Startup Therapy

Why Cofounders Often Don't Last Aug 16, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about cofounder breakup. Likened to marriage, having a cofounder requires commitment that comes with consequences when and if the Startup fails and coming up with an action plan when the business turns out to be a total flop.

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What to Listen For

00:00 Intro
00:33 Cofounders often don’t last
02:07 Cofounders should talk about what to do when things doesn’t work out
05:36 We make a binding contract with someone when the Startup longevity is uncertain
06:57 Founders don’t consider what to do if and when cofounders leave
09:16 Making a commitment at a time we know least about the outcome
14:24 Assumptions you’re making about your cofounder
21:10 Be prepared to deal with fundamentally different decision making
25:48 Plan for divorce but hope for a successful marriage
26:54 Start with a vesting agreement
31:33 Sign a commitment that when not met has consequences

The Case for Growing Slowly Aug 09, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about taking the slow growth approach. Instead of going full force too fast early on, take the time to understand whether the bets you’re paying back or not and when it’s time to change direction. Don’t follow the narrative that you need to accelerate right away. Follow the circumstances and consequences, and move at the pace that you’re supposed to take.

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What to Listen For

00:00 Intro
00:32 Dispel the myth about Startups should grow fast
01:57 Why do we feel we have to grow fast?
05:56 The car analogy: why early acceleration amplifies mistakes
08:34 The assumption we often miss is the factor of time
12:37 The best you do are the ones that you didn’t do
14:34 When you start to do too many things at the same time
17:30 Don’t mistake making bets into making good decisions
23:06 We get trapped in that repeatability phase
26:24 All the time we waste is a lot of money
29:59 The cost of accelerating the wrong people

Don't Rush Into Your Second Act Aug 04, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about founders rushing into building their next Startup. After a successful exit, most founders are overly eager to start their next big idea and land another win. They want to act upon it while they are in the momentum and prove that they aren’t a one-hit wonder.

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What to Listen For

00:00 Intro
00:36 Is it healthy to jump to the next Startup after you sold the first?
05:06 At some point you’ve already won, don’t rush to the next thing
09:08 Give yourself time to morph into an idea
13:12 The best ideas doesn’t often spring from boredom
17:21 All the best ideas started off small and dumb, but founders don’t think like that
23:03 Stories of founders who succeeded on their second act
27:58 Give yourself time to understand the drive and identify the false motivators
31:11 Take a little time to know the new you post exit

It's not What We Own - It's Whether It's Liquid Jul 26, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about liquidation probability. Many Startup founders make the wrong decision to lose interest in what they currently have and start pursuing something else in the hopes of a much bigger outcome, completely skipping the part where they first have to gauge the probability of success.

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What to Listen For

00:00 Intro
00:13 You should be more concerned about what you don’t own
05:40 The probability of liquidity is so low
09:06 The probability of your Startup getting liquidated and then liquidating the next
12:52 Important numbers: probability, equity that you own, and the value of equity
17:30 When the money you sold for is sitting on a preference
20:02 Probability should change the likelihood that you would sell
22:55 Always go with probabilities over percentage
26:57 We give up what we have and latch onto something with low probability
32:56 You only have so many years of peak earning potential

That Founder Sold for Too Little! Jul 21, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about opinions that do not matter when a company sells. A lot of founders are stigmatized for selling their Startups for too little. Too little in a sense that these non-founders only think of the numbers and not the value and work put into building the business. And the glaring truth is that they have never had that much money in their entire life! So their opinions aren’t valid.

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What to Listen For

00:00 Intro
00:53 To those who said, “That founder sold the company for too little.”
05:38 The lack of self-awareness of people making unnecessary comment
09:42 The unsolicited comment will constantly haunt the founder
13:46 Shooting back at the trolls just brings more trolls
17:49 $2M is $2M, how is that bad?
21:31 You can’t belittle $2M if you don’t have it
23:59 People are just chasing more without a clear objective
28:15 If the amount is relative to the founder’s needs, it’s a winning sale
30:00 Not all founders are able to sell their business
35:32 Founders shouldn’t lose sight of their accomplishment

When Can I Feel Good About Taking a Break as a Founder? Jul 19, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about putting every down for a much needed break. No, you can’t say, “I can’t take a break yet.” Or say, “Your hands are tied at the moment.” It’s critical that you take a break in between milestones, unless you want to get stuck on productivity and run dry on creativity.

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What to Listen For

00:00 Intro
00:24 When will you take a break?
05:08 Find milestones to fit in long-term breaks
10:37 Founders excel at planning but terrible at taking a break
13:41 When your only milestone to take a break is getting sick
18:59 If you recharge, you can do more work
22:48 The golden periods of creativity and analytical productivity
24:10 Get off, reset, and get back on with maximum energy
28:40 Some people aren’t taking PTOs
32:20 The concept of multiplicity
33:52 You’re going to come back as a better version of yourself

Forget Big Ideas - Start with Your North Star Jul 14, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about focusing on what you are trying to achieve before taking action on any big ideas you might have. Some of these ideas don't necessarily lead you to where you want to go. Some, if pursued, just end up in failures and frustrations. Instead, focus on where you want to go and then figure out how you want to get there.

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What to Listen For

00:00 Intro
00:24 Getting stuck in looking or working on an idea
03:41 Your business idea should align with what you love to do
06:46 Aspirations change as we age
11:00 Making a business out of something you’re good at
17:59 Specific goals makes it easy to map things around it
23:05 Every founder knows what to avoid
27:21 Just stop doing things that make you unhappy
31:29 When you’re using the wrong yardstick to measure growth
35:24 How to get paid for what you enjoy doing

Adding Staff Isn't a Sign of Success, Adding Revenue Is Jul 12, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about how increasing your staff does not necessarily mean growth, but a deliberate liability. Many people just focus on increasing the number of their employees and do not think about the cost of hiring more people. Yes, you need more people to get work done faster. Yes, you need additional minds to pitch in new ideas. But what if your revenue is lower than the liabilities?

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What to Listen For

00:00 Intro
00:39 Some people use staff count as a measure of success
03:40 A growing staff is only seen as a progress
07:01 Management strain continues as you add more people
10:48 There’s a diminishing return in every additional hire
14:28 Each new person that comes in is a burden in some form
16:08 Why do we associate hiring people with growth?
20:11 Putting people on payroll is easy, paying the payroll isn’t
24:33 Look at every choice as a possible liability
26:30 What can we do to keep revenue and stay efficient with staffing?
28:32 Getting additional funding to add people and accelerate things
32:13 If the Startup doesn’t work, you’ll regret adding more people

The Curse of the 37-Year Old Founder Jul 07, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about the dues founders pay for neglecting their health. Pushing yourself too much, putting your body through so much pressure, and then ignoring the warning signs as they come, you’re unconsciously trading your life for the success of your company. Don’t curse yourself in the process!

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What to Listen For

00:00 Intro
00:43 When you’re running your life too fast, you’re sacrificing your health
07:50 Processing all of life by not processing it
14:26 Because your body can adapt to anything, you shrug off any symptom
18:07 Early in our careers, we’re not aware of these problems
21:38 Founders rarely have a support structure
25:09 We're responsible for the conditions that created the liabilities
27:18 It’s difficult to admit you’re wrong when you made the bad decision
29:44 A lot of founders have had a massive panic attack at 37
32:28 When you’re deteriorating, why aren’t you doing something about it?
35:31 Your family can help spot the warning signs, but they won’t be
39:14 At your age, how much stamina do you still have?
40:53 How to avoid destroying yourself as your Startup grows
43:21 We assume that we’re the only ones going through it

When Our Startup Works for Everyone But Us Jul 05, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about what happens when things work for everyone else but not for you. The effort founders put into our Startup is a sacrifice in all forms and shapes, to the extent of spending less time with family, neglecting our health, or even getting a pay cut just to keep the business rolling. Yes, you are the founder but you’ve become a slave to your own business.

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What to Listen For

00:00 Intro
00:11 Things are going great for everyone except for you
04:20 Concepts that led to you being a founder
07:17 We're essentially mortgaging our goals without realizing it
12:36 When we take an investor, the investor becomes our boss
15:32 You need to set goals that are unchangeable
21:24 There is a threshold where commitment becomes destructive
26:12 It’s disruptive when you pick up on things your employees didn’t do

Can You Change People? Jun 30, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about changing a person’s personality (or the attempt to do so). It’s one of the factors founders cannot control and it’s silly to keep telling the same person what they should be doing more than once. It’s a waste of energy, a waste of time, and definitely a lost cause. Put your time and effort into someone else!

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What to Listen For

00:00 Intro
00:22 Trying to enforce behavioral change in your people
04:32 Them being a jerk is just reflection of our bad leadership
08:40 Skills: the things you can do, Personality: the things you can’t do
11:59 We keep thinking that we are the solution to the problem
16:54 Set an environment with a healthy culture people can mimic
20:56 Do not allow performance to outweigh the emotional wellbeing of the business
23:03 What would the problem look like if the person isn’t making it worse?
27:49 You shouldn’t be telling people to work harder
33:39 Ask yourself: Am I parenting or managing?
36:35 Personality issues are some of the problems founders can’t control

The Last Mile is the Most Important Jun 28, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about burnout when you’re nearly at the end of your Startup journey. Every sacrifice and risk you’ve taken will become useless if you feel tired and decide to take a break at the most crucial time and that’s when you’re at the last step of closing the deal. The trick is to surround yourself with people who will help you get through this phase.

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What to Listen For

00:00 Intro
00:55 What happens when we’re near the end of the deal?
05:53 Startup equity is the most expensive currency one can spend
09:31 When you just want to be done with it
11:56 What else can you do to motivate yourself?
17:54 Being vulnerable at this stage doesn’t allow for a second chance
20:21 What happens if you fall apart at the last moment?
24:53 Every hardship loses value if you drop everything now
28:10 There’s no version of a Startup that doesn’t have a burnout
32:01 Don’t go through this process alone

How We Leave is How We're Remembered Jun 23, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about avoiding unpleasant breakups. There always comes a time when you need to part ways with people, friends, staff, even investors. Every bad breakup can seriously damage your reputation in any means possible simply because some harbor vindictive emotions and speak negatively against you. What can you do then to avoid that?

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What to Listen For

00:00 Intro
00:22 How many good stories do you remember of breakups throughout your career?
03:55 Your poor actions is what people remember the most
06:21 Letting go of people means having more than one conversation
12:42 Your reputation takes years to build and takes seconds to destroy
17:23 The damage a single blown relationship can do
22:41 How handle breakups that usually end well
25:10 The need to justify yourself and your actions
28:25 It matters if they don’t feel mistreated when the breakup happens
34:04 A little touch can change the tone and reignite a soured relationship
38:58 We have to be structured and strategic with our words

What Happens to My Startup After I Sell? Jun 21, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about what happens after you sell your Startup. Beyond the big paycheck that will certainly make your life better, is the lingering attachment you have for your company and what becomes of it after you give up ownership and control over it. And what about the employees you’re leaving behind? Will they be well taken care of?

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What to Listen For

00:00 Intro
00:40 This fantasy of reaching this level when you want to sell your Startup
05:35 When you sell, how is everyone else in the organization affected?
08:59 From the one making the decisions to asking permission from someone else
14:01 Realizing that you have to step off the trail is a tough pill to swallow
17:51 It won’t be the same environment and a lot of people won’t stick around
23:26 This is about what to consider when you sell
26:02 Investors will only see you as a fall-in-line employee
32:08 If things were great, why do we want them to end?
39:17 It’s not just you, but the employees within the company

If We Want Power, We Create Power Jun 16, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about power struggle. A lot of us are used to hearing people telling us what we should and shouldn’t do, what we can and cannot achieve just because these people have tried it or have been in a similar situation. What they don’t realize though is the difference in capacity and skills. What works for them may not work for you, and what works for you didn’t work out for them.

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What to Listen For

00:00 Intro
00:27 The value in having a level of power and control in an agency
02:45 When having somebody else determine your destiny wasn't going to work for you
11:01 Setting your own path and not allowing anyone to tell you what to do
16:36 Stop listening to what everybody else is telling you to do
23:31 If you can do it once, you can do it again
27:10 What if the investors investing in you aren't what you should be focused on?
28:36 Attaining power that wasn’t handed to you gives a sense of inner peace
33:43 Set your own terms so other people can set their own
37:34 Figure out how to create power for yourself and extend it to the world

What will We Regret Risking for Our Startups? Jun 14, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about regret. Founders are bound to make decisions all the time. These decisions can make or break the Startup, and this is why regret is inevitable. Not all decisions bring a positive outcome, and when the outcome is the opposite of what you had anticipated, it’s part of the risk you’re taking.

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What to Listen For

00:00 Intro
00:33 Can you remember the first time you felt regret during a trade off?
05:15 The regret didn’t kick until later
07:43 Many of the risks that we’re putting up won’t return
11:39 We assume that we can make up for these risks
14:09 Don’t use the same pattern whenever you experience something new
17:28 When we form habits, we stop thinking about the different outcomes
21:32 Myth: No matter what the sacrifice is, you’ll be able to pay it back in the future
25:52 Going on a vacation but not really enjoying the vacation
27:25 We have to periodically reassess the sacrifices that we make
30:53 Founders are experts at manufacturing anxiety

Lessons from "Once Hot" Startups Jun 09, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about how we get blinded by the early signs of growth. When things go well, we tend to think it’s the golden moment and that your Startup is on it’s way to getting big, only to find out a week or a month later that you’re back at step one. Early stage successes become dangerous when we get blinded by them and start making the wrong decisions.

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What to Listen For

00:00 Intro
00:20 Early signals that tend to blind us from what we actually should be doing
04:54 It becomes dangerous when we start making decisions based on sudden growth
08:41 When things go well, it increases our vulnerability to make the wrong decisions
14:23 Yes, it’s going well, but you aren’t making any profit
19:24 It’s a mentality problem when we get too excited at the early stages
23:43 External signals sometimes send the wrong message
27:08 Don’t get blinded how well your product is received after launch

What If I Sell Too Early? Jun 07, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about when is the best time to sell your Startup. It’s a tedious process so you shouldn’t just focus on what’s happening during the negotiations but also the pros and cons after the sale is made. And of course, how much you’re being paid for selling is as important as HOW you’re getting paid.

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What to Listen For

00:00 Intro
00:11 “What happens if I sell too early?”
06:36 Buyers are often negotiating to pay for a company’s future value
10:17 Whatever cash you’re taking now might be the last cash you’ll ever get in the negotiations
15:10 It’s not about how much but HOW you’re getting paid
17:58 Myth: The maximum amount the company is worth is equal to how much the founder need
27:21 You have to be realistic that you might not be able to sell

Do We Need Offices Anymore? Jun 02, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about going back to an office setting. The idea that more work gets done inside the office is no longer as effective as it used to be. An office setting may not be that substantial anymore for Startups. A lot of businesses are being run remotely and by far, they are progressing well.

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What to Listen For

00:00 Intro
00:28 What happens when we return to our offices?
04:15 In current times, is an office really necessary?
08:47 Myth: We need an office to build culture
15:59 An office is the least likely way to build friendships
23:37 Myth: We need an office to get work done
27:20 Office equals work is no longer true
30:36 Slack and other project management tools can make collaborations happen
35:25 Collaboration versus coordination

Our Latest Success Might Be Our Last May 31, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about the notion that your current success will be the same for every Startup you build. While you’re in the momentum and when new ideas come in, you’re most likely tempted to venture into another Startup. Right? But, take a pause there and consider the odds of your success.

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What to Listen For

00:00 Intro
00:25 The notion that your current success will be lifetime
04:59 We think about our startup success the way people tend to think about career success
08:05 Sometimes, founders are just done and want to sell fast
14:36 We optimize for cost and revenue over time but unwilling to invest time when it’s over
18:28 We love to assume the outcome in that next hand and just carry forward
22:56 Stick around and work on every angle to achieve exponential liftoff
26:41 Pay attention to what you have in your hand at the moment
30:07 Successful Startups achieve success due to a ton of factors lining up at the same time

Do Socio-Political Issues Belong at Work? May 26, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about founders allowing open discussion of socio-political issues inside the workplace. Over the years, societal and political issues are topics that can either encourage healthy discussions and debates within the team or instigate friction and divide within the company. The question is, HOW do we talk about these issues?

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What to Listen For

00:00 Intro
00:25 Socio-political issues in a workplace
03:02 It’s important how and where we talk about these issues
05:55 Areas where we can start to have more productive conversations
10:51 Focus has a cost and it’s not that simple
14:44 Some socio-political issues are directly impacting people’s focus 11:39
18:03 Not all founders really care about other people’s issues outside of work
20:28 There are a lot of people in power that just don't understand these issues
25:43 Why this idea of just oppressing everything is just a broken hammer
32:00 Issues aside, what are the employees trying to accomplish?
36:34 Not everyone wants to be pulled into these discussions

The Superstar Advisor Sham May 24, 2021

In today’s Startup Therapy Podcast, Wil and Ryan ask, is it too early to get an advisor? Many Startup companies invest in an advisor to tap into connections that can possibly help raise additional capital. Yet, this investment does not promise successful returns because some introductions don’t end with the results founders are hoping for. The anticipated business meetings are never set.

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What to Listen For

00:00 Intro
00:28 How often were you asked to be a business advisor?
03:55 What's the guarantee that they want to know you?
07:08 If getting an advisor is just for raising the capital
09:31 One-sided conversations: what’s the biggest thing you can have getting an advisor
12:10 What if you make the introductions and nothing comes of it?
16:18 Ponder first if it’s the right time to invest in an investor
18:46 When people know more than you do, they just seem like geniuses
22:37 You can’t qualify an advice on a topic you’ve never understood
28:58 A good advisor will tell you what questions you should be asking
35:25 Advisors aren’t that bought in and won’t fully care

Startups are Built at the Expense of the Founder May 19, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about at what cost Startups are built on. What people often see is it’s all about raising money and getting external financial support, that additional funds are more than enough to keep the business going. But what people don’t see is the physical, mental, and emotional health that are being spent alongside a bloating debt.

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What to Listen For

00:00 Intro
00:24 The true currency spent when building a Startup
05:10 What are the personal costs for the founders?
09:05 Raising more money doesn’t make things any easier
19:31 Our Startups pull our health on different directions
23:58 Founders slowly lose connection with close relationships
29:00 Are you doing better than before you started your business?
33:13 If you’re well-being is failing, your Startup success won’t amount much

Why Nobody Returns Our Sacrifices? May 17, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about imaginary debt. A lot of founders are tied to this idea that employees will commit the same level of sacrifice as they would for the company. And that people will appreciate what they do and stick around no matter what happens. But it’s all an illusion. No one can actually match a founder’s willingness to sacrifice everything for the Startup.

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What to Listen For

00:00 Intro
00:48 When you feel indebted to the people in your team
06:26 Your team’s sacrifice is exponentially different from yours
09:43 Everyone else is going to be looking out for themselves
13:23 Founders find it difficult to get out of unhealthy situations
17:26 There is a point at which feeling indebted has a limit
20:28 No one actually takes care of the founders
25:27 The endless “I can’t” that binds the founders
29:11 Creating your own phantom conversations
30:09 You have zero right to expect that your sacrifices will be appreciated
34:39 Massive loyalty dissolves when a better offer comes
38:31 How to break free from the imaginary shackles

Even in Failure, Founders Deserve True Respect May 12, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about the most dreaded outcome - a failing Startup. When a business fails, founders often wallow over how people react and what they can say about the situation. The adverse reactions don’t matter. What should matter is who stays to help pull you out of the rubble.

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What to Listen For

00:00 Intro
00:19 Understanding how founders feel when a Startup fails
05:44 When you can’t deal with how people will process the failure
10:22 The Steve Jobs interview and dealing with criticisms
12:05 Do the people you’re concerned about actually have a voice in the situation?
17:14 Only founders who failed can sympathize with you
21:47 Surround yourself with people who knows what you’re going through
25:45 As a founder, how do you reach out?
29:58 When one founder is down, other founders should empathize and help

Can I Lead Without Being Liked? May 10, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about the pressures of leading a Startup team. It’s a Founder’s job to make difficult and unpopular decisions, even unconventional ones, which may merit the team's unfavorable reactions. Over time, these unpopular decisions make a Founder less likable. So then, at what point will being likable still matter?

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https://www.startups.com/begin
Join our Network of Top Founders
Send an email to therapy@startups.com

What to Listen For

00:00 Intro
00:30 As we lead, how important is it that we're liked?
05:29 Making fundamentally unpopular decisions to grow
11:56 When we’re starting, we build good relationships with people
16:00 You’re a cool boss but you aren’t invited in team lunches
19:23 The expectation for you to say ‘Yes’ all the time
21:47 What about when decisions don’t map back to you?
23:23 Even if you aren’t liked, you have to be respected
28:39 Everyone loves you, but you’re doing a bad job
32:43 Make difficult decisions but still empathize
37:22 As the organization grows, there will be more people not connected to you
39:39 Things you can do to seed some goodwill

When to Admit "I messed up." May 07, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about admitting you made a mistake. Oftentimes, it becomes difficult for leaders, including founders to admit that they’ve made the wrong decision or chose the wrong option. It’s the kind of vulnerability that no one wants to show. But if leaders can’t admit that they are wrong, no one else in the organization will.

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Resources:

Startup Therapy Podcast
https://www.startups.com/begin
Join our Network of Top Founders
Send an email to therapy@startups.com

What to Listen For

00:00 Intro
00:09 Founders fundamentally mess up and that’s okay
04:54 The longer you admit that something’s wrong, the worse it gets
10:32 COVID pushed organizations to strategically respond to the situation
16:26 Make people understand why you made a mistake
20:49 If founders can’t admit that “I messed up”, no one else will
23:25 When something goes wrong, it matters how you talk about it
28:23 Vulnerability comes with issues, but comes with benefits as well

Who is "Qualified to be a Founder"? May 03, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about the qualifications of becoming a founder. It turns out; anyone can become a founder. Having the idea and vision for your Startup is easy, but building a business out of nothing, dealing with potential issues and challenges, and getting started aren’t as easy.

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Resources:

Startup Therapy Podcast
https://www.startups.com/begin
Join our Network of Top Founders
Send an email to therapy@startups.com

What to Listen For

00:00 Intro
00:49 Congratulations on our 100th episode!
02:31 Recalling the early episodes
04:19 The topics are more focused on the Founders
08:43 Who is qualified to be a founder?
13:31 You have to be a guru when you start a business
16:50 Don’t be all things to your Startup
18:27 95% of all Startups is guesswork
22:57 Your expectations should include the iterative process
26:52 There’s just so much we haven’t seen
28:43 Unless you’ve been part of a fundraising process, you won’t understand how it works
33:25 Get third-party perspective
34:30 There's no parody in consequence

How to Sell the Vision Apr 26, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about selling a founder’s vision. The real struggle lies in convincing people that your vision, your idea can solve an existing problem. Startups often fail when the customers who are supposed to benefit from the product do not understand how it can serve their needs.

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What to Listen For

00:00 Intro
00:51 Back at a time when people ask: “What the hell is an internet?”
06:15 It won’t matter what you’re selling if the approach isn’t relevant
08:50 Ask yourself: “What problem are you solving?”
14:57 Founders often fail to set the problem that could potentially solve itself
19:14 Looking back into a business proposal that addressed an unrelatable problem
22:53 It’s essential to consider who you’re talking to when presenting your vision
26:49 The people you bring in will have a major definition of the company’s future
28:46 Be ready to explain how your vision will benefit others
31:25 If you can’t clearly define the problem, you can’t move forward
36:26 Do not assume that people can easily connect the dots

Manage Downside First - Big Opportunity Second Apr 19, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about planning for a downside strategy. Having a downside strategy allows for open conversations to conclude effective upside plans and address issues level-headedly. It’s a clear and sound path for founders to clean up a failing Startup.

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What to Listen For

00:00 Intro
00:29 Dealing with downsides forces difficult conversations
05:33 Downside strategies are a big part of any Startup
11:05 What is your tolerance for tough decisions?
18:14 Duration and severity of a downside
21:30 Know how to deal with a failing business
26:27 Establishing a threshold can make a difference
29:40 “When we worry about things, we tend to scale up to the biggest worry.” - Wil
32:10 Having a downside strategy allows for a powerful upside strategy
36:09 Build detailed downside strategies and be open to conversations

Why Money Can't Buy Happiness Apr 12, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about the correlation between money and happiness. Being successful and having a lot of money doesn’t equate to genuine happiness. More often than not, it’s a fleeting distraction from other issues that require attention. Money can only give you exhilarating yet passing moments.

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What to Listen For

00:00 Intro
00:10 Once you have money, are you truly happy?
04:15 With or without money, there’s always an issue to resolve
07:10 Wealth can only take care of the pain, but not buy real happiness
10:22 Money distracts you but can’t fix you
13:52 When the excitement fades, what else is left?
17:55 Spend time on your yourself, don’t get stuck on an outcome
21:48 At the end of the day, you’re still the same person
24:09 Analogy on the happiness of pursuit
27:10 Every milestone reached is often a fleeting moment

Is This the Right Cofounder? Apr 05, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about finding the right cofounder. It remains a challenge for Startup founders to find a business partner that doesn’t just have the best ideas, both should also see eye to eye when it comes to company growth and career goals.

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What to Listen For

00:00 Intro
00:35 Are you working with the right cofounder?
05:21 Not everyone is cut to be a founder
10:06 The consequences of committing to the wrong person
12:13 Signs that the partnership isn’t working
16:12 When there is friendship but lacking work partnership
23:17 It’s not about perfection, there are shortcomings too
26:41 You can’t test your cofounder until sh*t happens
32:24 Questions to ask when looking for a cofounder
36:06 How to prepare for a new partnership
38:36 Getting into an amicable breakup through conversations
42:08 Present terms that are beneficial for both party
46:52 It doesn’t benefit you yo blowup on someone

How Transparent Should I Be With My Staff? Mar 29, 2021

In this Startup Therapy Podcast, Wil and Ryan ask how much is too much when it comes to Founder transparency? Why many inner workings of your company should be on a need-to-know basis, how being a leader can mean holding your emotional cards close to your chest, and when being completely open can be too much.

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Never Tell People How Much Money You Have Mar 22, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about the disadvantages of having wealth. People are drawn to Founders who are successful, who have money to spare. Most of the time, people, including family, expect you to settle their financial issues just because you have the money. It reaches a point where you’re expected to spend your money and not expect anything in return. The toxicity is just too much when it happens too often.

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What to Listen For

00:00 Intro
00:26 Relationships and wealth
05:38 When people is all about wanting something from you
07:51 Some family members expect more from you
13:38 Founders are being judged by their wealth
16:41 Once you give something, you’re expected to give more
19:10 People tend to want to have your money too
23:24 Either way, you’ll be judged by how much cash you have
26:32 Assumptions are made when you have the means and resources
29:45 People with money can’t just give away what they have
33:29 The calls are now about financial matters, no more sincere connections
36:31 Everyone just wants to take from you but not willing to give back

Can Anyone Be as Committed as the Founder? Mar 15, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about commitment. There is a limit to the expectation you can set on others, and that your passion and commitment may not be as intense for the rest of your team. There are certain aspects of your Startup that you’ve got to shoulder on your own. After all, a founder’s superpower is the intensity of his commitment.

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What to Listen For

00:00 Intro
00:26 What is founder commitment?
03:53 The insane level of expectation founders have
07:22 Startup downside: letting go of people
12:00 Even with commitment, some people aren’t willing to deal with the downside
15:15 Not everyone shares the same expectation within the organization
19:02 Don’t set high expectations for other people
24:58 You can’t manipulate people into sharing your dream
25:57 Commitment is a founder’s superpower
27:16 There are certain things only founders should worry about

It Doesn't Matter Who Has the Bigger Startup Mar 08, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about the ugly truth about comparing your success to other businesses. When founders meet, the first person to speak often sets the tone of the conversation; many don’t even want to dig deep into the hardships one must endure to attain success. And is money the only metric for growth?

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What to Listen For

00:00 Intro
00:25 Drawing comparisons against other founders
03:03 The focus is often on the negative instead of what’s working
06:58 Comparing your performance to others just doesn't’ make sense
11:11 We often see the outcome but not the amount of work done
13:50 How do you perceive where you need to go?
17:04 At what point can you say, “I’m good”?
20:36 When a company grows, the focus shifts internally
23:05 Growth just for the sake of growth isn’t always true
26:12 Doing well with the things you really care about
28:50 Quit glossing over to avoid tough conversations
31:22 When things go down, which parts will matter?

How Founders Get Rich Without An Exit Mar 01, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about getting rich without selling your business. They discuss how getting too focused on getting rich causes missed opportunities, is selling your Startup necessary, the cash stacking effect, and spending money you haven’t earned yet.

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What to Listen For

00:00 Intro
00:09 Myth: Build big things to get rich
03:55 You miss other avenues for growth when you’re too focused on getting rich
05:31 The cash stacking effect
11:44 Getting regular pay versus never getting paid while running a startup
13:22 Planning to spend money you haven’t earned
16:52 “Aim for the likelihood of the outcome, not the size.” - Ryan Rutan
19:11 The broken idea of how to become rich
23:07 When did you start to feel rich?
28:26 Do you need to sell to get rich?
29:19 If there isn’t a need to, don’t sell

How to Make Potential Failure Less Scary Feb 22, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about getting through a Startup failure. While your mind can make it seem bigger than it is, most people won’t remember when a business shuts down, and that processing your emotions include assessing your failure to get back up!

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Resources:

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What to Listen For

00:00 Intro
00:10 What does failure really look like?
04:57 This is how people think about failure
09:21 When you’re focused on not failing instead of succeeding
11:19 Unpacking two filters of Startup failure
15:45 Your Startup failure isn’t as big as you think it is
20:58 What happens when you freak out
22:31 Over time, people forget about a company shutdown
26:34 Process the emotions, but get back up!
29:32 Unpack and assess your failure to manage it

Why Doesn't Anyone Understand What I'm Going Through? Feb 15, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about the hard part of being a founder - nobody understands what you do. Founders need people they can talk to about their job, someone mentally and emotionally willing to support their journey, and why the lack of support can hold them back.

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What to Listen For

00:00 Intro
00:12 Does anybody actually understand what founders do?
03:13 “Communication is the burden of the sender.”
04:52 Imagine being a founder is a job interview
08:25 Americans tend to ask people what they do
10:08 Only founders understand their fellow founders
13:23 It’s different when you cause everyone to lose their jobs
17:13 When you don’t get the support that you need
20:55 This is where founders are held up
25:12 Keep people who truly understand what you do

I Can't Have That, And That's Okay Feb 08, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about the cost of ambition. They discuss the levels in which aspiration is achieved, how starting a business involves: a series of unique conditions, the three basic levers of ambitions, and the uncertainty of the returns a founder has to consider.

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What to Listen For

00:00 Intro
00:21 There are things that you may not achieve at all
03:25 Not having something sometimes doesn’t matter
05:52 It’s not just ambitions, it involves a series of conditions to reach a certain threshold
11:44 “There are levels to which ambition alone can achieve.”
15:39 The cost of ambition becomes more than just our time
21:42 You know the cost, but what about the returns of your ambition?
26:45 Once you achieve something, how much are you willing to work for the next
32:17 The three basic levers of ambition

Many Startups Shutdown a Few Times Before They Succeed Feb 01, 2021

In today’s Startup Therapy Podcast, Wil and Ryan talk about the truth about Startup shutdowns. Shutdown cycles always happen to Startup businesses, several bad decisions don’t mean a complete failure, and second chances can happen when you’ve asked the critical Why’s.

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What to Listen For

00:00 Intro
00:59 Startup shutdown is always part of the process
07:05 Shutdowns had been happening even before COVID
12:15 When you assume you’re a failure because of several bad decisions
14:27 How bad was the mindset?
16:47 What was the turning point?
19:56 Rising back after a 48-hour downtime
24:59 Do-overs are what defines some of the great companies
28:46 Tips on how to restart a Startup
34:06 The looming danger when you can’t ask all the critical “Why?”
35:54 It starts with seeing a version 2 of the business to restart

When am I "too old" to Start a Startup? Jan 25, 2021

In today’s episode of Startup Therapy Podcast, Wil and Ryan talk about when it’s too late to launch a Startup. How gained experience equips founders to get through Startup challenges, the liabilities and the stakes involved when founders start late, why our 20’s is the golden decade to test and fail.

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Resources:

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What to Listen For

00:00 Intro
00:22 When is it too late to launch a Startup?
04:42 Deciding an end-point to your career
07:20 Our 20’s is a one-time get-out-of-jail free card
11:55 Gained experiences in building a Startup is the baseline of future endeavors
18:20 Missing important family moments
22:49 Mishaps will happen but the experience will get you through
25:09 Understanding the consequences of knowing the pattern from start to finish
28:45 You’re less employable at your peak age
31:47 Not all founders started at their 20’s
34:44 Starting in your 40’s is the most challenging times
37:00 50’s is the most expensive stage for founders
41:58 One of the challenges is, if not now, when?
43:09 Why young founders pivot so much
45:45 Passion and mastery produces different outcomes

What Do We Lose When We Sell Our Startups? Jan 18, 2021

In today’s episode of Startup Therapy Podcast, Wil and Ryan talk about the emotional toll on Founders when they sell their business, how to spend time when the Startup is gone, losing authority and level of importance, if there’s a way to prepare to become an ‘exited’ Founder.

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What to Listen For

00:00 Intro
00:25 Some of the potential downsides when selling a Startup
03:38 How much our Startup is tied to our sense of purpose
09:18 Concentration of excitement and purpose
13:21 That feeling of being needed
17:30 The horrible feeling of never being able to do it again
20:20 When you become an “ex” or “former” CEO
26:23 Without a business, how will you spend 16 hours a day?
30:40 Equating work hours to family time
34:12 Preparing to become an ‘exited’ founder

We Can't Keep Ignoring Founder Emotions Jan 11, 2021

In today’s episode of Startup Therapy Podcast, Wil and Ryan talk about the impact of Founders feeling uncomfortable about sharing their emotions, why you are being put in the wrong light, unpacking emotions to show vulnerability, and the difference between problems and emotions.

Listen in for more tips on being an approachable Founder!

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What to Listen For

00:00 Intro
00:44 Founders not feeling comfortable sharing their emotions
04:41 The pride and ego tide into the business
09:55 Why focus on other aspects of your business
13:30 How to unpack emotions and do something about it
21:15 Our problems and emotions are two separate things
26:10 Most founders keep their vulnerabilities
28:14 How being open impacts founder-team relationship
32:19 When everyone around puts you in the wrong light

Founders: All We Make are Bad Decisions Jan 04, 2021

In today’s episode of Startup Therapy Podcast, Wil and Ryan talk about using passion to pursue a business, how to differentiate novelty from passion, why founder burnout is common, and why identifying your theme is important before starting a business.

Listen in to test if you're passionate enough to start a business!

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What to Listen For

00:00 Intro
00:59 What moment turned into a passion?
05:02 Mistaking novelty as passion
08:42 The problem with purpose we all run into
14:14 When there’s no curiosity and passion, your role changes
17:13 Strategic planning: when growth is the only business metric
22:58 Find a theme that you’re passionate about
31:54 The energy in the early days can fade

The Benefit of a Hard Reset Nov 23, 2020

In today’s episode of Startup Therapy Podcast, Wil and Elliot talk about the benefits of a hard reset for a Startup, letting go of liabilities in exchange for a fresh start, and identifying priorities when going through a hard reset.

Listen in to know why a Startup reset can sometimes help save a business!

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What to Listen For

00:00 Intro
00:47 Benefits of a Startup's hard reset
04:16 Outsourcing based on what may happen
08:19 Part of a hard reset is getting fresh talents to join the team
12:27 With a rest, what does the staff look like?
15:12 Take inventory of the stuff that didn't work
18:20 Businesses walking away from monthly liabilities
22:06 Shred expenses and cut old agreements to reset
25:51 Sometimes, a start over is best to be profitable
27:51 If you're thoughtful, can build a more nimble business
30:01 Some hard events push for a reset, for decisions to be made

Why Every Founder Needs a Founder Group Nov 16, 2020

In today’s episode of Startup Therapy Podcast, Wil and Ryan talk about why founders need to belong in a therapy group, the benefits of voicing out your worries as an individual, and setting goals for yourself, not just your Startup.

Listen in to know how founders can effectively unload personal struggles!

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What to Listen For

00:00 Intro
00:58 How lonely are founders?
04:06 The things that founders can't share
10:22 Founders Group at Startups.com
14:37 How does trust develop within the founders group?
21:11 A group can't converse when they have differing ideas
28:35 Empathy for the members is equally important
33:03 The three questions to ask in every session
33:42 What keeps you up at night?
39:27 What do you need help with?
44:52 How can the community here support you?
47:51 Then, the founders talk about their goals
51:23 The point of a clarity call
52:35 Do you justify that every other goal is important, but yours?
54:43 When trust is established, the group can accomplish anything
56:06 Email us or visit groups.startups.com

When Are Founders Just Employees? Nov 09, 2020

In today’s episode of Startup Therapy Podcast, Wil and Elliot talk about how founders struggle to negotiate their compensation, what should happen in cap table discussions, and why founders should rethink how they get paid.

Listen in to get an idea how founders benefit more from their company!

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What to Listen For

00:00 Intro
00:50 What's going through your head?
02:21 When it isn't worth it anymore
06:02 The cap table discussion
09:26 When the thing you're most excited about is gone
11:46 Don't disincentivize employees by cramming them down
18:00 Have a conversation with investors to set the process you need to adhere to
21:25 Negotiate comp packages based on milestones
23:27 Founders should rethink how they get paid
25:12 What will make you keep working in the company?

We get Paid in Finishes, not Starts Nov 02, 2020

In today’s episode of Startup Therapy Podcast, Wil and Elliot talk about spending a decade to build a business from scratch, how past success can’t dictate the next success, and why nothing matters until the end goal is reached.

Listen in to learn how founders grow an idea into a successful Startup!

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What to Listen For

00:00 Welcome back to the Startup Therapy Podcast!
00:55 How long does it take to reach success?
02:28 The incubator project in 2001
03:39 The split in focus with multiple projects
07:54 How long will it take to prove a good idea?
10:33 Commit time to grow your company
12:03 Every idea is a bad idea unless you act on it
15:59 A problem you are willing to invest in
17:42 The early high-five indicators
18:55 What will a decade cost you?
22:03 "Don't work on something you don't care about." - Elliot Schneier
24:13 Focus and the right idea lead to success
27:04 Past success doesn't guarantee the next success
30:15 How do you explain commitment to new hires
31:22 Nothing matters until you reach the finish line

You Are NOT Your Startup Oct 26, 2020

In today’s episode of Startup Therapy Podcast, Wil and Ryan discuss why founders should separate themselves from their Startups, the lack of predecessors to guide young founders, what else to focus on besides building the business, and maintaining individuality.

Listen in to learn about individuality and separation from your Startup!

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What to Focus on to Get a Hit

[00:00:32] Are we a separate entity from our Startup?
[00:05:58] For founders, everything should have been right
[00:10:04] There's a pattern to follow, young founders don't have that
[00:11:24] There's a company that you do, it's not who you are
[00:16:01] It actually isn't validation, it's a relief
[00:18:14] Self-inflicted prison: you get stuck in your Startup
[00:20:06] It's not always about how your Startup is doing
[00:23:30] What do you do when you're not building your Startup?
[00:23:30] What can we do for other founders?
[00:26:33] Why is it affecting you at a personal level?
[00:29:14] Your Startup is not who you are

How to Translate What Investors Tell Us Oct 19, 2020

Our focus in today’s episode is listening to what investors are actually saying. Wil and Elliot discuss the direct and indirect ways investors say ‘No’, the passive-aggressive questions, when founders become annoying, and how investors should behave.

Listen in to learn how to translate what your investor is saying!

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What to Focus on to Get a Hit

[00:00:40] Why founders can't understand their investors?
[00:02:24] The NO's that sound 'Yes'
[00:06:18] Venture Community vs Angel Investors
[00:07:11] From an analyst to a partner
[00:09:38] Is it a yes or a no?
[00:10:35] Understanding the user pipeline and deal flow
[00:12:27] What happens when you press on investors
[00:15:45] When investors are interested, they'll blow you up
[00:17:55] Time kills deals
[00:19:34] If it's not a resounding Yes, it's probably a No
[00:22:04] The tendency to annoy investors when you can't take the hint
[00:25:12] Show investors a drastic demand in the product
[00:28:08] How should investors behave?
[00:34:28] Always make a statement in a question
[00:36:47] Education on a fairly complicated space
[00:38:20] The passive-aggressive questions
[00:42:00] Investors saying 'maybe'
[00:45:10] Investors should be definitive in saying 'No'

Why Don't We Feel Like We've Made It Oct 12, 2020

Our focus in today’s episode is how to get a hit on your business. Wil converses with Sam Parr, Co-Founder and CEO of The Hustle, a massively successful email newsletter to help entrepreneurs make smart business decisions fast by providing information in an easy to consume format.

Wil and Sam look back at the early stages of their Startups, how to gauge financial security, why an early start is an accelerant, tough conversations with investors, and incredible stories of successful Startup businesses.

Listen and learn how to get your first million!

What to Focus on to Get a Hit

[00:00:07] Welcome to the show, Sam Parr!
[00:01:18] The early days of the Hustle
[00:03:35] The gap between expectations and reality
[00:05:57] When you get your first million dollars
[00:07:37] The perks of balling out
[00:09:41] Business impacts the capitalist society
[00:12:31] Doing things that aren't just about safety
[00:13:42] Emotional instability, compounding level of anxiety
[00:15:07] Possibilities changes your worldview
[00:17:42] Success doesn't often equate to happiness
[00:19:21] What are the goals?
[00:22:27] What was your number for security?
[00:25:16] How agency and non-funded businesses grow
[00:28:24] Genuine appreciation for the hustle, for the grind
[00:31:54] A Man's Search for Meaning by Viktor Frankl
[00:35:22] We're built to get stuff done
[00:36:33] Remove the timeframe, fulfill your obligations
[00:38:59] Tough conversations with investors
[00:41:13] Victim mentality to get out of a bad deal
[00:42:06] The untold hustle stories
[00:44:32] Massive capital gains versus annual cash flow
[00:46:09] Stories of small operations minting profits
[00:50:28] What can you make that can last 50 years?
[00:53:31] When early success becomes an accelerant
[00:56:41] Four years from now, a 50 million net worth?
[00:58:55] If you're good at setting up a startup
[01:01:00] Hiring a person to stir the business
[01:04:00] The perks of financial stability
[01:06:45] What to focus on to get a hit

Why aren't Founders more Transparent? Oct 05, 2020

Our focus in today’s episode is transparency of founders about their startups. Wil converses with Andrew Warner, an internet, startup entrepreneur and founder of Mixergy.com. On Mixergy, proven entrepreneurs are invited to teach how they built their startups.

Wil and Andrew define the lines between genuine curiosity and transactional conversations in building relationships, how topics and answers have consequences, and getting people to open up about themselves by sharing a little bit of yours.

Listen to how transparency can affect business relationships.

Episode Resources

Mixergy.com - “Learn from Proven Entrepreneurs”

What to Listen For

[00:00:12] Who is Andrew Warner?
[00:02:02] Why aren't founders more transparent about their startups?
[00:02:48] Why do I have to talk about the loser stuff?
[00:05:23] A little bit of a personal backstory.
[00:08:15] Being open to others about your vulnerability.
[00:12:24] Everything has always worked until you fail.
[00:14:07] Nobody wants to hear how well you are doing.
[00:15:08] If you do not have the tools of being vulnerable.
[00:16:16] People are always craving to be transparent of some things and hide others.
[00:19:01] The moment you're vulnerable, you become less defensive.
[00:20:45] What are some areas you don't feel talking about publicly?
[00:23:09] When one openly becomes honest and vulnerable, everyone becomes honest and vulnerable.
[00:26:48] Be genuinely curious to get people to open up.
[00:28:34] Do you need to share a little bit to get some during interviews?
[00:30:38] Ask a double-barrel question to give some room for sensitivity.
[00:32:00] Being vulnerable makes building relationships faster.
[00:34:52] Transactional relationships won't help build real connections.
[00:38:33] Actually listen and give leading questions to actually connect.
[00:39:44] When people sit with you more and more, they value your time.
[00:44:34] Incapability of small talk, possibly a fatal flaw.
[00:46:49] How to disarm someone so full of himself.
[00:52:32] Ask very personal questions to further relationships.
[00:57:51] The topics and answers that have consequences.
[00:59:16] Look for topics that people do not need to defend.
[01:01:46] Be prepared for backfires.
[01:04:18] Do you wish you can take back what you've overshared?
[01:08:30] Tell people if you're uncomfortable sharing something.
[01:09:20] We connect with people with their flaws, it makes us human.

What Do We Owe Our Employees? Sep 28, 2020

For Startups, what exactly do we owe our employees and to what extent?

In this episode of the Startup Therapy Podcast, Wil Schroter & Elliot Schneier redefines the unwritten social contract between employers and employees, the problems that arise when issues remain unheard, and how transparency has changed the leadership approach of Startups.

Listen in to hear why transparent leadership builds valuable trust!

Episode Resources:

Send us your questions - Therapy@Startups.com
Email coaching@startups.com for Startups Coaching sessions

What To Listen For:

[00:01:14] There's a lot that employees rightfully feel they are owed.
[00:03:03] Some employee journeys are their first journey and founders should at least explain to them what they don't know.
[00:07:00] Most major problems are always mapped back to someone who wasn't heard.
[00:10:23] It's easier to just tell people what to do when a problem arises, but taking time to listen to employees builds so much trust both ways.
[00:13:05] The paranoia about the concept of communicating in a transparent way.
[00:17:43] Transparency and honesty can be an adequate form of compensation.
[00:19:07] Bringing the staff into conversations, makes them feel like teammates instead of cogs.
[00:24:03] If you can't attach humility to your leadership, you really start to lose credibility.
[00:27:47] Old school draconian type of work environment isn't getting you the top talents anymore.
[00:31:43] Listening style of leadership is more natural than the learned-style approach.
[00:35:02] Now, people feel comfortable enough to converse organizationally with leaders.
[00:37:33] "Do it because I said so," is a very weak argument.
[00:38:42] That social contract that we owe has created more human relationships, a metric of happiness.
[00:40:49] The more opportunity to have less problems amongst everyone, it's easier to lead a company.

[00:43:30] Don't hesitate to reach out to us at coaching@startups.com.

Why No One Tells Founders, It's Over, Move On Sep 21, 2020

Are you working yourself into the ground without making much progress, if any?

In this episode of the Startup Therapy Podcast, Wil Schroter & Elliot Schneier break down the failure of their company AffordIt, what actually happens when you run out of VC money, and when you should drop the ego & focus on doing what’s best for your mental health instead.

Listen in to hear what our VC’s did when we ran out of money!

Episode Resources:

Send us your questions - Therapy@Startups.com
Sign up for the Startups Newsletter - https://www.startups.com/newsletter

What To Listen For:

[00:00:12] - Welcome Elliot!
[00:01:12] - The failure of AffordIt
[00:02:42] - What happens when you run out of money from your captial raise?
[00:05:19] - Obtaining VC in hard economic times
[00:07:35] - What happens if you take on investors and don't become a unicorn?
[00:10:12] - How to fail gracefully & maintain relationships
[00:11:12] - Is it the investor's job to call when to fold the business?
[00:13:08] - What we wished our investors would have done
[00:15:35] - The importance of mental health in leadership and why no one cared at the time
[00:18:04] - If investors won't advise you in critical moments, who will?
[00:22:34] - The group that shatters your ego as a Founder the most
[00:28:12] - AffordIt's breaking point
[00:31:10] - The perfect person to tell you you're done
[00:32:32] - Not sure if it's time for you to fold the tents or have a question? Email us at Therapy@Startups.com
[00:36:57] - You don't have to run out of money to fold the tent

The Advisory Board Aug 10, 2020

Do you really need an advisory board?

In this episode of Startup Therapy, Ryan Rutan and Wil Schroter talk about why an advisory board is important, how to build your own board of advisors, and creating connections that will lead you to endless opportunities.

Listen in for tips on getting advisors to expand your Startup network.

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What To Listen For:

[00:00:58] The Advisory Board
[00:02:03] Why is an Advisory Board important?
[00:06:02] How do you decide who joins the Advisory Board?
[00:07:44] The Board members are interchangeable.
[00:13:03] Advisers aren't that hard to get.
[00:15:06] How to ask someone to be in the Advisory Board?
[00:18:53] Don't get worked up on the number, get worked up on the quality.
[00:21:17] These people must have perennial advice.
[00:24:40] Connect to people who might be helpful to you and the business. Build a network.
[00:25:53] Even if you lack credibility, connections can get you where you need to be.
[00:27:16] One person can give you the answer and fast forward everything.
[00:31:08] "If you want to get advice, raise capital. And if you want to, raise capital, try to get advice."

How Do We Create Career Paths Within Startups? Aug 03, 2020

Want to get your best employees to stick around?

In this episode of Startup Therapy, Ryan Rutan and Wil Schroter talk about how contribution outweighs years of service, capabilities dictate career progression, and why Startups enable accelerated career growth.

Listen in for tips on expanding careers without the hierarchy.

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What To Listen For:

[00:02:20] Hierarchy isn't necessary for people on the team to grow.
[00:06:34] We want as flat of an organization as possible.
[00:10:05] What happens when you move to another company
[00:11:50] Growth essentially needs to be unpacked.
[00:15:31] Cash needs to align with contribution.
[00:20:09] Opportunity wherein you can't go to another company because you pay the most in your current position.
[00:22:54] Understand what's motivating folks to stay.
[00:28:28] The reflection of your progression is through your capabilities.
[00:30:27] Position progression shouldn't have anything to do with managing people.
[00:33:33] Don't look at the years of experience, anyone can level up.
[00:36:19] Measure employee value by contributions, not by time employed.
[00:39:26] In smaller companies you can get your hands on stuff you couldn't touch before.
[00:42:45] People can outgrow the company, or grow faster than the company's growth.
[00:44:55] Title progression is not bound by who's ahead of you.

Early Retirement Is a Broken Concept Jul 27, 2020

Have you planned your retirement?

In this episode of Startup Therapy, Ryan Rutan and Wil Schroter discuss why retirement goals should start now, how early testing changes your plans, and what objectives to set immediately.

Tune in for more retirement opportunities in your Startup game.

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What To Listen For:

[00:01:06] Retirement is this day and age isn't what it used to be.
[00:03:00] This concept of retirement. The work many of us do just doesn't have the same kind of drudgery that it used that retirement is the safety net from pain.
[00:05:00] It's about spending some more time doing things that you are already doing.
[00:07:56] Our startups should be helping us to get to our goals without necessarily having to sell.
[00:09:11] Deferred living: You can work on a startup for decades and not have it sell, and if you didn't design it towards that every day enjoyment.
[00:11:00] Retirement should be the things that you want to do. And the question is, how much of it can I do right now?
[00:12:50] Ease into it, figure out that one thing you want to do.
[00:18:30] It's like popping a bubble. If you just pop the bubble on whatever that dream is and it's still interesting, okay there's something there worth stressing for.
[00:22:05] With retirement, we would have endless choices of what to. But can you spend 16 hours a day with something that isn't a job.
[00:25:00] For any major life event transition, you should be testing, you should be preparing yourself.
[00:26:20] Retirement should be something that you're constantly chipping away at, by creating more opportunities to spend the time the way you want it.
[00:28:00] If we look at retirement as a gateway, we can't retire. The ability to play tests is there, there's no reason you can't be doing these things.
[00:30:18] I don't think there are a lot of hobbies that activate us the way our jobs do.
[00:32:34] Do you really think that top performing professional athletes were still playing because they need the money? It wasn't retirement because they achieved financial success, they had satisfied themselves.
[00:34:14] There's a huge difference between wanting to retire and wanting to not do something you're already doing.
[00:34:55] The ultimate goal of retirement is that nothing changes, because all along we deliberately planned to get more and more time to do things we want to do.
[00:37:00] Instead of waiting for this amazing moment that can change it all, change a number of things year end, year out, eventually the things you want to do during retirement are already in place.

Why We Say "No" Jul 20, 2020

Does "No" mean never? Not exactly.

Today on the Startup Therapy Podcast, Wil & Ryan discuss why saying "No" is just as much discipline as it is a luxury, how to build your confidence in saying "No", and when saying "No" can actually grow your business.

Whatever you do, don't say "No" to this episode!

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How Much Money Does it Take to Be Rich? Jul 13, 2020

Do you have safety assets for your next milestone bet?

In this episode of Startup Therapy, Ryan Rutan and Wil Schroter discuss the difference between personal and business safety, an optimized approach to running a Startup, and creating a safety net for every milestone.

Listen in and learn how base-level stability can fundamentally change a business.

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What To Listen For:

[00:00:33] How can I feel safe from Startup scam?
[00:02:10] Safety can be achieved at a much lower threshold. Now that I am safe, how do I become rich?
[00:06:22] Personal safety vs Business safety
[00:09:40] Optimizing approach to building a Startup
[00:12:06] What safety looks like as a milestone?
[00:13:40] Safety means you can weather a storm. What is a storm to you?
[00:17:03] Startup narrative: What safety really is and how important is it for businesses?
[00:19:31] Having a safety net allows you to do things you couldn't do.
[00:21:11] Establish real, specific milestones
[00:23:45] The safety that businesses should be looking for.
[00:25:49] Isolate your milestones, put your bet on something that doesn't impact your safety.
[00:27:00] Create base-level stability for the business.
[00:29:17] How focusing on getting to that safe point can fundamentally change the business.
[00:32:43] Once you're safe, becoming rich becomes a luxury goal.
[00:34:00] What do you need to be safe enough to make really big bets?
[00:36:18] Figure out exactly what safety looks like.

Optimize for the Probability of an Outcome, Not the Size Jul 06, 2020

Eager to prove that your business idea is the next big thing?

In this episode of Startup Therapy, Ryan Rutan and Wil Schroter discuss how to get more out of short-term goals, finding validation for Startup growth, and why funding doesn’t equal success.

Listen in and learn how to optimize probability for the best possible outcome!

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What To Listen For:

[00:00:36] At what point was not aiming big enough the problem?
[00:03:01] Trying to hypothesize how big it could possibly be when you don't even know if it works when it's still small?
[00:07:49] You could start with one broken argument that says, well, it's going to take the same amount of time to build…
[00:13:37] You don't just set one goal and you kind of hang out until you hit that one goal.
[00:21:15] It now has to be a giant business to somehow have some sense for validation.
[00:22:08] You probably also don't need the funding to do a good job in that market.
[00:29:26] Make it work in a microcosm and then make it work somewhere else.

Founder Reputation Jun 29, 2020

Reputation: we all have an understanding of the long term & lasting impacts it has on your standing as a Founder, but how do we cultivate our reputation?

Today we discuss why reputation is so important, how your resume & reputation are two very different things, and what the cost incurred if we don't take our reputations seriously.

Remember, your reputation is very hard to build & very easy to destroy - so listen up!

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How Do I Leave My Startup Stress at Work? Jun 22, 2020

As a Founder, running a Startup is inherently stressful, right? Wrong!

Today we discuss why self-imposed stress is often unproductive and imagined, a few tactics to try that will help you leave Startup stress at work, and how to be more present when you are home.

Listen in to learn how to relax!

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Why Can't I Be Happy Where I Am? Jun 15, 2020

Why is it that as Founders, we feel like we must constantly be chasing something - otherwise we don't feel satisfied?

But sometimes happiness isn't just about reaching milestones & crossing finish lines, so today we talk about why you're probably running from your fears, unpack our own flawed logic behind not taking a moment to celebrate our own successes, and you can take that much needed moment to breathe for yourself.

Listen in to find peace within Startup chaos!

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Are Big Cities Better For Startups? Jun 08, 2020

Is it better to live as a Startup Founder in a major city?

In this episode of Startup Therapy, Ryan Rutan and Wil Schroter discuss working from home, where to locate a company, and their experiences living in different areas.

Tune in to hear the benefits and setbacks of being in a major city.

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What To Listen For:

[00:00:33] What are the pros and cons of being in a big city at this point?
- The pros are things like networking locally and easily socializing, the cons are lack of space and the costs are higher.
[00:17:52] How has working from home currently changing how people live and work.
- People will see how easy it is to move and live in different locations.
[00:21:39] What’s the benefit of moving to a place with cheaper housing?
- You can get a palace with is much nicer than cramped city living.
[00:32:26] What about the importance of socialization?
- Socialization is done outside of working together.

Sometimes Shrinking is the Right Move Jun 01, 2020

Can downsizing your Startup be the right move for you?

In this episode of Startup Therapy, Ryan Rutan and Wil Schroter speak on the appropriate sizing of businesses, understanding the health of a business, and the importance of communicating these changes with your team.

Listen in to foster the longevity of your business.

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How Founders Should Communicate in a Crisis May 25, 2020

Do you have tactics that can be deployed to help manage during a crisis?

In this episode of Startup Therapy, Ryan Rutan and Wil Schroer talk on the crisis’ they’ve dealt with in the past, what works in managing during those instances, and beneficial communication tactics.

Tune in learn how to best communicate amidst chaos!

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What To Listen For:

[00:00:19] Their experience with going through crisis’
[00:08:00] What happens after a crisis
[00:10:23] How they dealt with the 2000 - 2008 financial crisis
[00:12:25] Zirtual financial mismanagement
[00:15:10] Lessons learned from handling crisis’
[00:30:22] On problematic communication during a crisis
[00:35:25] Get everybody on the same side of the table

Opportunities In a Recession May 18, 2020

Do you feel like the recession is bringing your Startup to a standstill?

In this episode of Startup Therapy, Ryan Rutan and Wil Schroer discuss how to make this recession beneficial for your business, how to delegate and refocus, and why you should buy-in during the recession.

Listen in and learn how to optimize and weather the storm!

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Bringing On An Investor Means Hiring Your Boss May 11, 2020

Does bringing on an investor mean you’re hiring you’re own boss?

In this episode of Startup Therapy, Ryan Rutan and Wil Schroter discuss, what happens once we close the deal with investors, the nature of the relationship between the investors and the Founders, and the decision of hiring your own boss.

Tune in to understand how having investors could alter your business mode.

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Treat Departing Employees Like Future Employees May 04, 2020

Have you thought about the inevitability of an employee leaving your Startup?

On this episode of Startup Therapy, Ryan Rutan and Wil Schroter discuss how former employees can be either an asset or a liability, learning to not take an employee leaving personally, and extending yourself to help them in their career path even after they leave.

Listen in and learn how to encourage a happy send-off culture!

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Forget Compensation, Let's Talk About Quality of Life Apr 27, 2020

Shouldn’t we still have health, happiness, and comfort while trying to grow a Startup?

On this episode of Startup Therapy, Ryan Rutan and Wil Schroter discuss why it’s important to focus on quality of life as a Founder, giving yourself permission to enjoy and take care of yourself, and the power of quality of life as a form of compensation.

Tune in and learn to take quality of life seriously!

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What If This Was Our Last Startup? Apr 20, 2020

What if we determined that what we're doing now is the thing we want to be doing for the rest of our lives?

On this episode of Startup Therapy, Ryan Rutan and Wil Schroter discuss the fulfillment of finishing, the dynamic of passion within mastery, and the habit of deferred living.

Listen in and learn to take advantage of the moment!

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What If the Founder Personality is a Liability For the Startup? Apr 13, 2020

Are you aware that how you respond to difficult situations affects whether or not the best solutions will be created?

On this episode of Startup Therapy, Ryan Rutan and Wil Schroter discuss emotional intelligence, how your EQ affects business health, and why it’s important as a Founder to be self-aware that your personality influences the organization.

Listen in to learn why emotional intelligence is important!

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It's a Marathon - Not a Sprint Apr 06, 2020

Do you know what it looks like to pace yourself for the long run as a Founder?

On today’s episode of Startup Therapy, Ryan Rutan and Wil Schroter talk about how to set your pace, how sprinting is an easy trap to fall into, and what happens when you push yourself too hard.

Remember, it’s a marathon - not a sprint!

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What Should We Teach Kids About Entrepreneurship? Mar 29, 2020

As parents and potential parents, what should we be teaching kids about Startup companies?

On today’s episode of Startup Therapy, Ryan Rutan and Wil Schroter talk about how entrepreneurship is not taught formally, the benefit of teaching it at a young age, and how ownership of ideas is important to a child’s intellectual growth.

Tune in to learn what can be done to nurture the entrepreneurial spirit in children.

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Is it Okay to Show My Flaws? Mar 22, 2020

When is it okay for a Founder to be open with their team and business partners about their personal problems?

On this episode of Startup Therapy, Wil Schroter & Ryan Rutan open up about their past & current struggles with anxiety, health issues, and being overly critical with themselves and their Startups.

Listen in to hear how we’ve come to learn to deal with our flaws in a healthy and productive manner, it can be done!

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Celebrate Tiny Wins Like Super Bowls Mar 15, 2020

Starting a company is hard, growing a Startup is slow, and frankly there aren't many Super Bowl type moments. Don't get discouraged, instead celebrate the small wins because the small wins daily lead to success over time.

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Will Somebody Try to Steal My Startup Idea? Mar 08, 2020

Surely by now we've all seen The Social Network, but how much of a concern is it really if someone tries to steal our idea?

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What Problems Go Away With Time? Mar 01, 2020

Running a Startup can be chaotic, we know this, but is it true that problems will go away with time? Not necessarily. Some do, some don't, listen in to learn how & when to align your expectations for the unexpected.

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When Will My Startup Make Me Happier? Feb 23, 2020

Starting a Startup is brutal, hard work - at what point do our companies finally start to pay us back?

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Is a $0 Salary a Badge of Honor? Feb 16, 2020

The $0 salary, is it the cool & honorable thing to do, or is it completely & utterly ridiculous? We'll find out today on this episode of Startup Therapy.

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What Happens After I'm Successful? Feb 09, 2020

On today's episode of Startup Therapy we answer the question: what happens after we achieve the success we've worked so hard to get?

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Is Doing Non-Startup Stuff Good For My Startup? Feb 02, 2020

We talk a lot about how much time we spend on our Startups, but what about doing stuff that's not Startup related? On today's episode of Startup Therapy we discuss why this important - not only for your own sanity, but for the growth of your company.

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The Side Hustle Jan 26, 2020

On today's episode of Startup Therapy we're going to talk about the often misunderstood "Side Hustle" - why it's important, where it fits into Startup Life, and how to survive it... or when it's time to quit.

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Do Founders Need to be Good Managers? Dec 15, 2019

As Founders, the day you incorporate your company you become a manager. Today on Startup Therapy we talk about why management is important, how no one's truly qualified for this role, and if you, as a Founder, even need to be your own manager.

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Fat, Sick, and Nearly Startup Dec 09, 2019

As Founders, how can we deal with personal hardships that are often a result of our own Startups - while we're still running them? On today's episode of Startup Therapy, we share very personal stories of our own struggles with health and well-being as we built Startups.com

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I've Lost Interest In My Startup - Now What? Nov 25, 2019

Ever caught yourself thinking - I don't love my Startup like I used to? Today we talk about similarities between relationships and Startups, why it's okay if the passion really has faded away, and a few actionable things you can do about it to help move on.

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Bouncing Back from Failure Nov 18, 2019

It's a fact, most Startups fail...but we never actually think that could happen to ours, right? In today's episode of Startup Therapy we talk about how to bounce back from failure, why it's not as bad as it sounds, and we share our own stories of past failures.

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Founder Groups Nov 11, 2019

The Founder's journey can be a lonely one, but it doesn't have to be. In today's episode of Startup Therapy, we talk about why you should consider hosting Founder Groups, how they're helpful, and how they've helped us with our Startups.

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What to Expect in the First Year Nov 04, 2019

As Founders, we think we know how our products and businesses will look and function for years to come, but as with time it's nearly impossible to expect the unexpected. In today's episode of the Startup Therapy podcast, we discuss what our Startups looked like in year 1, so you might have a better idea of what to expect in your first year too.

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Overwhelmed. Oct 28, 2019

As a Founder, do you find yourself overwhelmed...and frustrated that things aren't moving forward as fast as you like? Startups are often portrayed as a go big or go home affair, and as Founders it's easy to get caught up chasing monumental goals and forget about the daily actions that will actually get us there.

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Why Am I So Lonely? Oct 21, 2019

As a Founder, do you find yourself feeling isolated, anxious, or alone? We've all heard the phrase, "it's lonely at the top", but as Founders we do far more than hear it...we live it. On today's Startup Therapy, we're going to talk about why loneliness is part of the Founder journey and what we can do to minimize the negative impacts it has on our lives, our families, and our Startups.

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How Do I Get People to Take Me Seriously? Oct 14, 2019

As a Founder, does it feel like every time you walk into a room you're being judged before a single word comes out of your mouth? Do you feel like it's always an uphill battle to be taken seriously? On today's Startup Therapy, we'll look at why it takes so much work to be taken seriously and what we can do to thumb the scales in our favor.

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How Much Is Our Freedom Worth? Oct 07, 2019

As Founders we value our freedom, but how much? When was the last time you considered the value, and the cost, of your freedom as a Founder? On today's episode of Startup Therapy, we'll discuss both sides of the Founder Freedom coin - the costs and the benefits.

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How Do I Quit My Own Startup? Sep 30, 2019

As Founders, we know that Startups fail, and we end up moving on, but what happens when a Startup's doing really well but we want to move on anyway? On today's episode we discuss the reasons you may be compelled to quit your own Startup, how to fill the role you leave empty, and what life after quitting might look like.

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Can I Have a Boss Again? Sep 23, 2019

As a Founder, I've asked myself...can I ever be an employee again? What happens if I'm forced into reporting to someone else now that I've tasted the freedom of Founderhood. Maybe you have too? On today's Startup Therapy, we'll discuss what happens when you have to stop being a boss and start having one.

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Am I Safe? Sep 16, 2019

As a Founder, when the business is struggling it can feel that that struggle is linked to your personal life, your personal safety, and you could suffer greatly as a result. On today's Startup Therapy podcast we'll talk about how important it is to isolate feelings of startup peril from those of personal safety, for your good and that of the business.

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Things We Don't Want To Do Sep 09, 2019

As Founders we spend a lot of time thinking about what we want to accomplish, but have you ever sat down and really given thought to using the freedom that comes with being a Founder to say, "Here's some things I NEVER want to do again"? On today's episode, we talk about the power of reducing stress by building a Startup we love, in an environment intentionally designed to avoid the things we loathe.

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Work From Home Sep 02, 2019

Is remote work bullshit? In today's episode of the Startup Therapy podcast were going to talk about when and how remote work & work-from-home policies can really have a positive impact on a Startup.

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My Company is Worth Millions...Why Am I Broke? Aug 26, 2019

Does the idea of building a business worth millions that leaves you, as the Founder, broke seem unfair? On today's episode of the Startup Therapy podcast we'll explore why building something of great value doesn't directly or immediately turn into value for us, as Founders.

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Should I Pay People With Equity? Aug 19, 2019

Paying people with equity is a time-honored tradition in cash-starved startup land, however, have you ever stopped to consider the real cost? In today's Startup Therapy podcast we'll talk about the real cost of treating equity like cash when it represents 100% of the future return on your efforts.

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When Should Someone Else Run My Company? Aug 12, 2019

On today's Startup Therapy podcast we're going to discuss why superior managerial skills don't necessarily trump a Founder's passion and knowledge as a company scales, and how to decide what to let go of...and when.

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The Cost of Toxic Employees Aug 05, 2019

We all know the value of having a star player on our team or an amazing co-Founder, but what about the opposite? On today's episode of the Startup Therapy podcast, we'll discuss how to handle, identify, and handle toxic teammates before their impact spreads across the organization.

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An Exit Plan Jul 29, 2019

As Founders, we're all familiar with the concept of an exit plan. In today's Startup Therapy podcast we discuss what you actually CAN plan for, what happens if you don't plan at all, or if you don't actually want to sell.

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How Much Should I Be Working? Jul 22, 2019

When was the last time you asked yourself - "How much should I actually be working?" Probably never because the answer is obvious, 24/7 right? In today's Startup Therapy podcast we're going to dig into the notion that more hours equal more growth. While there's truth to that assumption, we'll explore how to think quality and not quantity when it comes to your weekly punch card.

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Should I Regret Not Raising Capital? Jul 15, 2019

Have you ever asked yourself, do I need to raise capital to be successful? In today's episode of Startup Therapy, we'll talk about you why probably don't need to regret NOT raising capital, at least not yet.

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Burnt. Out. Jul 08, 2019

How are you feeling today? Chances are, as a Founder - some version of tired, worn out, mentally foggy, or stressed part of the answer. Today, we're going to dive into burn out. How to see it coming, how to avoid it, and how to recharge when you've gone too far.

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Steve Blank - When Startups Shed Their Skin Jul 05, 2019

In today's bonus episode, we talk to Steve Blank - the godfather of Silicon Valley

Learn more about your ad choices. Visit megaphone.fm/adchoices

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Am I a Fraud? Jul 01, 2019

As a Founder, when was the last time you felt like you had no idea what you were doing? Today we talk about why feeling like a fraud is actually a very normal part of Founder life.

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Work Life Balance Jun 24, 2019

Stay longer. Work harder. Sleep less...as startup Founders we've all gone through periods where this felt necessary. Today we'll talk about what you can do to balance life and startup, and why it's actually beneficial for you and your startup to do so.

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Preparing Your Spouse For a Startup Jun 17, 2019

As a Founder, you've likely spent years in the build-up to actually starting your company, but how much time did you dedicate to preparing your spouse for the leap into entrepreneurship?

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Equity Doesn't Mean Equal Jun 10, 2019

50-50, even-Steven, when splitting equity equal is best, right? Today on the Startup Therapy podcast we discuss why cutting things right down the middle is rarely fair to start and only gets further out of balance as time goes on.

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How to Shut Down Gracefully Jun 03, 2019

Why is it everyone talks about starting companies, but nobody ever tells us how to shut them down? Today on the Startup Therapy podcast we'll cover how to wind down a startup with as much grace as possible.

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Growth Isn't Always Good May 27, 2019

What if I told you growth doesn't always make a startup better? Today on the Startup Therapy podcast we're going to talk about why the focus should be making our startups better, not just bigger.

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Your Advisors are Probably Wrong May 20, 2019

What if the advice you're getting from the smartest people you know...is wrong?

Today on the Startup Therapy Podcast we'll discuss how to seek advice, how to ensure you're getting the best advice, and how not to fall into the trap of letting other people's experiences dictate your actions.

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How I Harness My Startup Anxiety May 13, 2019

Does your startup produce more anxiety than revenue? Does your morning routine consist of running down an endless list of worries? Do you lie awake at night and regret ever starting your business? Today we're going to explore why anxiety is a part of every founder's life.

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How Much to Pay Yourself May 06, 2019

As a Founder, should your startup's salary be on par with whatever you were making at your last job? Or should you tough it out and not get paid at all? The answer is probably neither of those options.

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When to Raise Funds Apr 29, 2019

One of the most common questions among Founders is - Do I have to raise money for my startup?

What that question generally means is: "Can you tell me how to raise money and where to find it?"

Sure, every startup could put more money to use but does every startup need funding?

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Startups Don't Go Bankrupt, Founders Do Apr 22, 2019

What if you could be completely broke, on the verge of bankruptcy at home, while still running a thriving business?

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Life After a Startup Exit Ain't All Rosy Apr 15, 2019

There are endless stories about Founders cashing out on their startups - but what happens to those Founders after the exit? Are they happier for it? If not, then how does that affect the path that current Founders are on? Wil and Ryan dive into real post-mortems of what happens to Founders after they sell their company, and the painful emotional issues that come with life post-exit.

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$250k is a Life-Changing Exit Apr 08, 2019

When we think about "startup exits" we think about "millions and billions". But how life-changing could an exit of as "little" as $250,000 be? A lot more than you might think, which is important because most people are far more likely to get to a $250k exit than millions or billions. Wil and Ryan unpack exactly how $250k could fundamentally change your life and how trying to get to that milestone first could be a more achievable and powerful goal than holding out for the big Willy Wonka ticket.

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Your Degree Means Nothing Here Apr 01, 2019

A true startup is a meritocracy where big degrees and titles shouldn't determine how capable your team is or how fast each person can grow. We talk about creating an environment where each team member can put their past accomplishments aside and focus exclusively on what they have contributed to the startup today.

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When to Fold the Tents Mar 18, 2019

If you find yourself focusing more on not losing than winning then it could be time to fold the tents and pack up camp, but when should you make that call?

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Optimizing Your Startup for Happiness Mar 16, 2019

What if instead of focusing our startup around our product or revenue - we started optimizing for our own happiness? What if our work hours gave us more time with our kids or who we worked with were only the people we enjoyed the most? It's possible! The key is thinking about your startup differently by using "personal happiness" as a core tenet of how the company works.

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A $1 Million Business is a Home Run Mar 11, 2019

In the age of "unicorn valuations" and giant funding rounds, the world has lost sight of how valuable a startup can be with even a million dollars of revenue. Ryan and Wil do a detailed walk through of exactly how important a million dollar business can be to a Founder and how dangerous it is to be lead astray by big numbers that have very little personal value to a you as a Founder.

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Stop Comparing Yourself to Other Startups Mar 11, 2019

Many of us play a horrible game of comparison, whereby we compare ourselves to other Founders, other startups, and if we're (un)lucky, the press and social media barrage we see of other people's success. It's all BS. The moment we start comparing ourselves to other people's apparent success, we all lose. In this episode we talk about how to "stay in your own lane" and avoid the fallacy of following false idols in the startup world.

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The Emotional Cost of Being a Startup Founder Mar 11, 2019

No one talks about the intense emotional cost of being a startup Founder (so of course we do!) From missing time with your loved ones to putting all of your chips on a single bet (and losing), we talk about the toll this takes on a Founder and what you can do to help alleviate some of this intense stress in your own journey.

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The Problem with Working on Multiple Ideas at Once Mar 11, 2019

Wil and Ryan debunk the myth that startup Founders can work on multiple ideas at once and just pick the best one to run with. We unpack the issues that come with trying to split your focus and how costly that decision can be.

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