Startup Therapy

Latest Episodes:

You Only Have to Be Right Once Feb 24, 2025

Show notes

In this episode of the Startup Therapy podcast, Ryan and Will chat about how startup success isn’t always a straight path. They use Mark Cuban’s story as a prime example, showing why sticking it out for the long run is so important—because success can happen at any time in a founder’s career. They also talk about how those early small wins can build up to something bigger and why setting strict timelines for success doesn’t really make sense. At the end of the day, one big right moment in a 50-year career can be a total game-changer.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:07 The Reality of Founders' Success

02:00 Mark Cuban's Journey to Billionaire Status

06:35 The Importance of Small Wins

10:15 Financial Stability and Early Success

15:57 The Value of Consistent Small Wins

18:02 Success Doesn't Have a Timeline

18:12 When Does Success Happen?

18:20 Examples of Late Bloomers

18:45 The Myth of Early Success

19:59 The Impact of Timing

20:44 The Internet Era and Young Wealth

21:40 Outliers and Unrealistic Expectations

25:13 Consequences of Chasing Quick Success

27:28 The Value of Longevity in Business

30:02 Unexpected Success Stories

31:46 Staying in the Game

32:36 Join the Startups.com Community

What Would I do Differently Feb 03, 2025

Show notes

In this episode of The Startup Therapy, Ryan Rutan and Will Schroter explore the 'what if' scenarios that often preoccupy founders. Will shares personal milestones, showing how taking bigger risks shaped his journey. They discuss the hidden costs of success, the pitfalls of romanticizing alternative outcomes, and the importance of realistic risk assessment. The key takeaway? Embrace risk to avoid the regret of missed opportunities.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:

00:07 – Reflecting on milestones and 'what ifs'
00:44 – The risks and rewards of entrepreneurship
04:00 – A hilarious temp job experience
07:34 – The reality of alternate paths
09:02 – The danger of romanticizing 'what ifs'
13:48 – The cost of success
15:29 – Building a realistic mental model
16:18 – Stop guessing and get real answers
16:26 – The cost of staying in a job you hate
17:30 – Should you stay or leave?
18:10 – The true cost of success
19:12 – The hindsight trap: romanticizing outcomes
21:56 – Learning from failure and modeling risk
22:55 – Zirtual acquisition: a case study in risk
28:47 – Surviving failure and moving forward
31:35 – Avoiding regret and embracing risk

When Can I Afford to GAMBLE? Jan 27, 2025

Show notes

In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroter dive into an interesting perspective: taking risks in entrepreneurship is actually a luxury, not the norm. They break down what it really costs to take risks, how to figure out your "minimum viable risk pool," and why having a financial cushion is key to surviving setbacks.

They share personal stories from their experience at Startups.com, emphasizing the importance of cutting personal and business expenses to stretch your runway and make smarter decisions. This episode is all about helping entrepreneurs understand the financial milestones they need to hit to keep their businesses afloat—and how time plays a big role in navigating risks.

This episode is packed with advice for anyone trying to manage the tricky balance of risk and reward in entrepreneurship. Tune in to learn how to take smarter risks and build a solid foundation for your business!

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:15 Why Taking Risks Is a Luxury

02:08 Balancing Personal and Business Costs

03:44 Lessons from Startups.com

05:55 Why You Need a Risk Buffer

10:25 Figuring Out the Minimum Viable Risk Pool

16:51 Financial Discipline and Budgeting

19:09 The Freedom Fund Explained

26:51 How to Survive Financial Challenges

Can Founders Find Contentment? Jan 21, 2025

Show notes

In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroeter delve into the anxiety surrounding contentment in the startup ecosystem. They question the conventional wisdom that equates contentment with stagnation and probes whether startup founders should aim for contentment as a goal. Through personal anecdotes and industry examples, they explore the influence of perpetual ambition and societal expectations on entrepreneurs. They also discuss the differences between being content and being complacent and reflect on the continuous urge to chase new problems and challenges, even when previous goals have been achieved.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:44 Questioning the Need for a Business Coach
02:05 The Dilemma of Contentment vs. Ambition
04:02 Reflecting on Milestones and Contentment
07:35 The Nature of the Startup World
15:23 Anxiety as a Driving Force
20:51 The Anxiety of High Achievers
22:11 The Pressure of Success: Avicii and Pharrell
23:59 Imposter Syndrome Among Overachievers
26:21 The Elusive Goal of Contentment
29:08 Balancing Ambition and Contentment
33:29 The Trap of Endless Ambition
40:44 Finding True Satisfaction

Why do Investors FIRE Founders? Jan 13, 2025

Show notes

Ryan Rutan and Will Schroeter discuss the complexities and challenges faced by startup founders, particularly the frequent occurrence of founders being replaced by investors. The conversation delves into the motivations behind such investor decisions, the difficulties in replicating a founder's passion and vision, and the common pitfalls and consequences of these transitions. The hosts share personal anecdotes and provide insights on how to prevent these situations, handle them professionally if they arise, and maintain valuable stakeholder relationships. This episode is a must-listen for any startup founder navigating the turbulent waters of investor relations and company growth.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:

00:25 The Downfall of Bench and Ian Crosby's Story
01:54 Investor Motivations and Founder Replacements
03:33 Understanding Investor Expectations
05:40 The Slow Burn of Founder Dismissal
08:23 The Impact of Replacing Founders
13:49 Personal Stories of Founder Replacement
16:47 The Challenges of Replacing Founders
19:26 Augmenting the Team vs. Replacing the Founder
22:01 Why Investors Push Founders Out
24:00 Navigating Earn-Out Periods in Acquisitions
24:26 The Challenge of Replacing Founders
26:43 Timing the Transition: Leadership vs. Management
29:08 The Mercenary CEO: Pros and Cons
35:31 Investor Expectations and Founder Realities
42:19 Handling Founder Exits Professionally

The Burden of Unrealistic Expectations Dec 02, 2024

Show notes

In this episode Ryan and Will delve into the intense pressures faced by founders from investors, peers, and the startup community. They discuss how these external expectations often drive founders to pursue goals misaligned with their personal beliefs and values. The conversation explores how unchecked expectations can lead to burnout and misguided efforts. They share insights on the importance of auditing and resetting personal and business expectations to ensure they align with one's true goals and values. The hosts also highlight the dangers of comparing oneself to other founders or industry giants, and emphasize the significance of building a business that meets personal fulfillment rather than external benchmarks.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/st...
Website
https://www.startups.com/begin
LinkedIn
/ startups-co

Join our Network of Top Founders
Wil Schroter
/ wilschroter
Ryan Rutan
/ ryan-rutan

What to listen for:
00:32 The Source of Pressure and Expectations
03:32 Investor Expectations and Their Impact
04:05 Personal Story: Missing Investor Expectations
05:44 The Reality of Investor Expectations
10:15 Comparing Yourself to Other Founders
17:45 The Peer Comparison Trap
18:06 Personal Journey: From Poverty to Success
20:01 The Futility of Social Media Comparisons
23:07 Tying Success to Self-Worth
28:20 The Illusion of Goals and Success
31:53 Reevaluating Startup Expectations
36:43 Conclusion: Building What Matters to You

How do I Stay Positive In Tough Times? Nov 25, 2024

Show notes

Ryan and Will discuss the omnipresent challenges that come with running a startup. They delve into the perpetual 'shit storm' that founders face and share practical advice on how to keep moving forward even when everything feels like it's falling apart. Key points include regaining perspective, converting anxiety into actionable tasks, breaking down large goals into manageable micro-goals, and finding healthy obsessions to channel stress. They emphasize the importance of maintaining a positive outlook, not just for personal sanity but for the wellbeing of the entire team, and share personal anecdotes and strategies that have helped them through their toughest times.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/st...
Website
https://www.startups.com/begin
LinkedIn
/ startups-co

Join our Network of Top Founders
Wil Schroter
/ wilschroter
Ryan Rutan
/ ryan-rutan

What to listen for:
00:07 The Perpetual Shit Storm of Startups
01:01 Practical Advice for Founders in Crisis
02:10 Regaining Perspective During Tough Times
05:08 Personal Stories of Overcoming Challenges
15:29 The Importance of Taking Action
20:41 Managing Anxiety with Side Tasks
21:58 The Power of Micro Goals
23:37 Breaking Down Big Tasks
26:29 The Importance of Focus
32:07 Finding Healthy Obsessions
41:08 Building Momentum with Small Wins
43:14 Join the Startups.com Community

Are Investors Trying to Push Us a Cliff? Nov 18, 2024

Show notes

In this episode of the Startup Therapy Podcast, Ryan and Will delve into the often misunderstood motivations of venture capitalists. They discuss why investors push startups to grow rapidly, the pressures VCs face to deliver returns within a specific timeframe, and the fundamental differences between the stakes for founders and investors. The episode uncovers the reasons behind the 'push you off a cliff' approach, the impact of the 2 and 20 model on VC behavior, and the importance of understanding these dynamics to better navigate the startup journey.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/st...
Website
https://www.startups.com/begin
LinkedIn
/ startups-co

Join our Network of Top Founders
Wil Schroter
/ wilschroter
Ryan Rutan
/ ryan-rutan

What to listen for:
00:11 Understanding Investor Motivations
01:12 The VC Time Crunch
03:57 Profit vs. Growth: A VC Perspective
13:25 The Reality of VC Salaries
16:29 Founders vs. Investors: Different Stakes
19:00 Conclusion: Aligning Goals with Investors

What Previously Funded Founders Do Differently Nov 11, 2024

Show notes

In this episode of the Startup Therapy Podcast, Ryan and Will discuss the daunting realities of raising capital for startups. By sharing insights and experiences from both first-time and repeat founders, they delve into the recurring theme of regret found amongst entrepreneurs who've gone through the funding process. Topics include the hidden costs of raising money, the pitfalls of losing focus, and the challenges of working with investors. The hosts offer practical advice on when to raise funds, how to mitigate the risks of distraction, and the importance of being selective and strategic about bringing investors on board. Whether you're gearing up for your first round of fundraising or re-evaluating your approach, this episode provides valuable lessons to help navigate the complex landscape of startup financing.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/st...
Website
https://www.startups.com/begin
LinkedIn
/ startups-co

Join our Network of Top Founders
Wil Schroter
/ wilschroter
Ryan Rutan
/ ryan-rutan

What to listen for:
00:14 The Reality of Raising Funds
00:38 Founders' Regrets and Reflections
02:15 The Perils of Not Getting Paid
04:22 Understanding Founder Compensation
11:04 Strategies for Better Compensation
13:24 Challenges with Profitable Companies
15:02 The Pressure to Grow or Bust
15:16 The Dilemma of Raising Too Early
15:47 The Vulnerability of Early Stages
16:22 The Importance of Timing in Fundraising
16:56 The Pitfalls of Early Funding
17:28 The Distraction of Fundraising
20:34 The Impact of Investor Expectations
28:23 The Challenge of Having a New Boss
31:50 Key Takeaways and Final Thoughts

Are Startups Easier for Experienced Founders? Nov 04, 2024

Show notes

In this episode of the Startup Therapy Podcast, Ryan and Will debunk the myth that each startup venture becomes progressively easier with experience. They explore the truths and fallacies surrounding repeat entrepreneurship, sharing personal anecdotes and insights from their extensive history of building and acquiring startups. Discussing expectation management, the double-edged sword of experience, and the harsh realities of repeating past mistakes, Ryan and Will emphasize that while experience offers certain advantages, it does not guarantee success in new ventures. They also highlight the emotional resilience required to endure the cyclical nature of startup challenges and the ever-present difficulties of achieving product-market fit and successful marketing, regardless of prior victories.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/st...
Website
https://www.startups.com/begin
LinkedIn
/ startups-co

Join our Network of Top Founders
Wil Schroter
/ wilschroter
Ryan Rutan
/ ryan-rutan

What to listen for:
00:15 Debunking the Myth of Easier Startups
01:27 The Double-Edged Sword of Experience
02:32 Drawing from Multiple Experience Buckets
05:15 Expectation Management in Startups
09:39 Avoiding Duplicate Mistakes
13:01 Raising Capital: Lessons Learned
15:16 The Value of Experience in Decision Making
17:07 The Reality of Investor Promises
17:17 Understanding People: A Founder's Key Skill
18:38 Emotional Maturity in Leadership
20:00 Challenges That Never Get Easier
21:57 The Ever-Changing Landscape of Product Market Fit
25:39 Marketing Struggles for Experienced Founders
27:40 The Pain of Failure: It Never Gets Easier
31:30 The Value of Experience and the Role of Luck
32:38 Join the Startups.com Community

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