Startups For the Rest of Us

Latest Episodes:

Episode 623 | TinySeed Tales s3e3: Paternity Leave Sep 15, 2022

Show notes

In the third episode of season 3 of TinySeed Tales, Rob Walling checks in with Tony Chan of CloudForecast to see how he is faring since his co-founder is now on paternity leave.

During this time, Tony shares a big win along with dealing with some hiring and growth setbacks.

Topics we cover:

1:24 - How the business is doing while Francois is on paternity leave
2:36 - Tony’s perspective on being a solo founder for the past 6 weeks
5:04 - Managing your own founder psychology
7:49 - How Tony is dealing with an unexpected sales slump
16:16 - Did Tony end up hiring a full-time SDR?
21:04 - Dealing with setbacks
22:41 - What Tony is looking forward to in the next couple of months

Links from the Show:

Tony Chan (@toeknee123) I Twitter
CloudForecast
TinySeed Applications are now open
Episode 613 | Hacking Your Founder Psychology
Summit

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you.

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Episode 622 | Making Hard Product Decisions & Growth vs. Profitability with Derrick Reimer Sep 13, 2022

Show notes

In episode 622, join Rob Walling and fan favorite Derrick Reimer, the founder of SavvyCal, as they discuss topics like balancing profitability versus growth and deciding which features to build and not. They chat about some specific features that Derek has decided to build, those he has not decided to build, and the thought process behind them.

Topics we cover:

4:02 - Making product decisions
9:22 - Deciding on what features you are not going to build
19:12 - When to reply to debates on Twitter
27:42 - Twitter’s newsletter feature
31:40 - Derrick’s perspective on balancing profitability vs reinvesting in the business
43:10 - Is Rob scratching his maker itch by being an investor in companies through TinySeed, or is he missing building SaaS businesses?
46:29 - Should Rob join TikTok?

Links from the Show:

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you.

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Episode 621 | TinySeed Tales s3e2: Onboarding Their First Hires Sep 08, 2022

Show notes

In this episode of TinySeed Tales, Rob chats with Tony Chan from CloudForecast about the progress his rapidly growing team has made over the previous few weeks.

Tony is riding the roller coaster that is entrepreneurship and in this episode you get to follow along.

Topics we cover:

1:47 - New full time engineering hire onboarding results
4:50 - Part time SDR hire onboarding results
7:31 - How hiring affects company culture
10:19 - Tony’s biggest wins in the last few weeks
14:30 - Growing the product to grow Expansion Revenue
15:45 - CloudForecast’s summer sales lull
19:40 - Keeping sane as a founder
22:00 - What Tony is worried about coming out of summer
24:00 - The next MRR target

Links from the Show:

Tony Chan (@toeknee123) I Twitter
CloudForecast
TinySeed Applications open September 12, 2022
TinySeed Tales S2E1 I Introducing Gather
TinySeed Tales 1 I A Non-Technical Saas Founder

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you.

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Episode 620 | Finding SaaS Ideas, Customer Pain, SaaS Metrics, and More Listener Questions Sep 06, 2022

Show notes

In episode 620, join Rob Walling for a solo adventure as he answers some listener questions. These questions range from which SaaS business metrics to pay attention to and how to find good SaaS ideas to helping an employee transition from a task-level to a project-level thinker.

Topics we cover:

1:44- What SaaS business metrics matter the most?
11:21- Do you have any general observations about building a SaaS for non-technical customers?
16:00- How do you find a good SaaS idea?
24:41- How can I assist an employee in transitioning from a task-level to a project-level thinker?

Links from the Show:

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you.

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Episode 619 | TinySeed Tales s3e1: Moving from Bootstrapped to Mostly Bootstrapped Sep 01, 2022

Show notes

Welcome to Season 3 of TinySeed Tales, where we follow the founders of one SaaS startup throughout a year as they share their struggles, victories, and failures.

On the first episode of Season 3, Rob introduces us to Tony Chan, the cofounder of CloudForecast. CloudForecast is a daily AWS cost monitoring service for busy engineering teams. Tony is one of 33 startup founders from TinySeed’s Spring 2021 accelerator batch.

Topics we cover:

2:41- What’s CloudForecast?
4:09- How large is the CloudForecast team?
6:54- Why did Tony apply to TinySeed?
8:30- Why Tony turned down venture capital offers?
13:48- Tony reflects on the added complexity of taking funding
19:47- Tony’s biggest fear
22:34- What is Tony looking forward to?

Links from the Show:

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you.

Episode 618 | How to Achieve Financial Freedom Aug 30, 2022

Show notes

In episode 618, join Rob Walling as he chats with Sam Dogen, the founder of Financial Samurai, which is one of the longest-running and most popular personal finance blogs. Over the last 13 years, Sam has personally written over 2,500 essays along with a Wall Street Journal Bestselling book. We talk about achieving financial freedom, money mindsets, and relentless execution.

Topics we cover:

3:12- The 4% Rule
4:40- Sam’s alternative approach to the 4% Rule
7:25- The FIRE Movement
10:16- How to navigate the US health insurance system as an early retiree
12:10- Sam’s relentless execution when it comes to running Financial Samurai
17:40- How Sam learned about personal finance
18:47- How Sam negotiated a severance package despite quitting his investment banking job
22:47- Why he runs Financial Samurai as a true lifestyle business
26:07- Would Sam sell Financial Samurai for $20 million?
27:35- The premise of Sam’s new book
28:46- Sam’s mental model for allocating financial assets to generate passive income

Links from the Show:

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you.

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Episode 617 | News Roundup: Profitwell $200M Exit, Spreadsheet Mentality, and Watching an Acquirer Ruin Your Company Aug 23, 2022

Show notes

In episode 617, Einar Vollset and Tracy Osborn join Rob Walling for a bootstrapper news roundup episode. They cover a wide range of topics from ProfitWell’s big 200 million exit, spreadsheet mentality, watching an acquirer ruin your company, and much more.

Topics we cover:

[3:06] What’s your take on ProfitWell’s acquisition?

[5:52] Watching an acquirer ruin your company

[14:03] The spreadsheet mentality

[23:09] If you can’t buy it twice, don’t buy it

[36:00] Balancing realism with optimism as a founder

Links from the Show:

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you.

Subscribe & Review: iTunes | Spotify | Stitcher

Episode 616 | An 8-Figure SaaS Founder's Approach to Remote Work Aug 16, 2022

Show notes

In episode 616, Rob Walling chats with Liam Martin, the co-founder of Time Doctor and author of the new book, “Running Remote: Master the Lessons from the World’s Most Successful Remote Work Pioneers.” We dig into the fundamentals of asynchronous communication, how to do remote work better, and some surprises they saw during the pandemic.

Episode Sponsor

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Topics we cover:

[2:46] What Liam has learned running Time Doctor for the past 12 years

[6:23] Can extroverts thrive long-term in a remote work environment?

[11:14] Liam’s approach to metrics and KPIs for engineering teams

[18:23] Why remote companies that move faster collaborate less

[21:31] How far can you take async communication in a remote team

[24:29] Combating isolation on remote teams

Links from the Show:

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you.

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Episode 615 | Bootstrappable Businesses, Cargo Culting, and How Pricing Affects Growth (A Rob Solo Adventure) Aug 09, 2022

Show notes

In episode 615, join Rob Walling for a solo adventure where he covers what makes a business bootstrappable (and things to avoid), cargo culting, and how large of a business you can build at different customer lifetime value levels.

Episode Sponsor:

Topics we cover:

[1:51] What makes a business bootstrappable?

[14:15] Cargo culting

[20:05] How large of a business can you build at a specific annual contract value or lifetime value?

Links from the Show:

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you.

Subscribe & Review: iTunes | Spotify | Stitcher

Episode 614 | Deciding When to Quit Your Day Job, Founder Anxiety, and More Listener Questions Aug 02, 2022

Show notes

In episode 614, Rob Walling chats with fan favorite Derrick Reimer. They start out by talking about Derrick’s decision to take a sabbatical from The Art of Product podcast after co-hosting it with Ben Orenstein for more than 5 years. Then, they answer a handful of listener questions, including when to quit your day job to focus on your startup full-time, coping with anxiety as a second-time founder, and choosing a domain name.

Episode Sponsor:

Topics we cover:

[2:18] Derrick’s decision to take a break from The Art of The Product podcast

[10:22] When should you go full-time on your startup?

[17:20] Before looking for tech firms, should I know the best frontend and backend architecture for my SaaS MVP and then only shop for firms who specialize in that?

[24:13] I'm starting a new SaaS business, and despite a previous successful experience, I can't stop feeling extremely anxious about it. Is this something you're familiar with? How did you deal with it?

[30:34] When choosing a domain name for my startup, should you go with a meaningful and expressive name, but a less serious TLD.io or a somewhat fictional name combined with the best tld.com?

Links from the Show:

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you.

Subscribe & Review: iTunes | Spotify | Stitcher