In Episode 567, Rob Walling chats with Don Pottinger about joining a company as a developer, transitioning to CTO within 6 months, buying the company for $1, and then later on selling it for a life-changing sum of money.



The topics we cover



[1:13] Introductions



[4:08] Learning to code independently vs learning on the job



[06:38] Joining Kevy in 2014



[8:00] Transitioning to Director of Engineering and then to CTO



[11:58] Difficulty of laying employees off



[14:20] A new CEO and $0 MRR



[16:08] Cap table difficulties



[19:56] CEO departure and buying the company for $1



[26:30] Starting over and doing it solo



[29:01] Running as a lifestyle business and selling the company



[35:02] Launching a new startup



Links from the show




Kevy



Langua Talk



Don Pottinger (@donpottinger) | Twitter




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 567 | From Developer to CTO to Buying the Company for $1

The original podcast for bootstrapped and mostly bootstrapped startups, this show follow the stories of founders as they start, acquire, and grow SaaS companies. Hear when they fail, struggle, succeed, and take you with them through the tumultuous life of a SaaS founder. If you like Mixergy, This Week in Startups, or SaaStr, you’ll enjoy Startup for the Rest of Us.

Business

Investing

Careers

Management & Marketing

Business News

Shopping

Marketing

Management

Entrepreneurship

In episode 709, join Rob Walling for a solo adventure as he shares his story of growing his personal wealth over the past few decades. Selling companies was the major driver of wealth, but he also explores the role of cryptocurrency, running profitable companies, and angel investing. Rob emphasizes the power of entrepreneurship in achieving financial freedom, while acknowledging there are ways to do so while keeping risk relatively low.



Episode Sponsor:





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Topics we cover: 




2:50 – A lesson on how to build wealth



4:31 – Entrepreneurship was our biggest tool



6:37 – Building, acquiring, then selling companies



10:45 – Building slowly while staying risk-averse



13:27 – Investing in riskier assets like cryptocurrency



19:39 – Running profitable companies



20:56 – Angel investing, and WP Engine



23:44 – Traditional, salaried employment



24:53 – Typical investments: stocks, bonds, REITs



27:36 – Real estate investing




Links from the Show: 




MicroConf Connect



Christopher Gimmer (@cgimmer) | X



Christopher’s tweet



Sherry Walling (@sherrywalling) | X



The Stair Step Method of Bootstrapping



Start Small Stay Small by Rob Walling



This Took 11 Years to Be An "Overnight Success" - SaaS Exit Strategy



Zen Founder



The SaaS Playbook by Rob Walling



WP Engine



TinySeed



Barbell Strategy Explained for Stock and Bond Investors




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.

Episode 709 | The 7 Greatest Investments of My Life

In episode 708, Rob Walling and Derrick Reimer tackle listener questions about building development skills vs. business skills and strategies for entering competitive markets. They also chat about building on top of AI services, addressing the risks of platform dependency and the importance of managing infrastructure costs. 



Episode Sponsor:





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Visit DevSquad.com/startups and get 10% off the first three months of your engagement.



Topics we cover: 




02:38 - Should you build technical skills or business skills?



11:41- Entering a competitive market



21:14 - Building a valuable analytics dashboard tool



29:29 - When should a solo founder hire for marketing roles?



36:29 - The rare skillset of a full-stack marketer 



38:18 - Implications of building on openAI and scaling infrastructure costs




Links from the Show: 




Register for MicroConf US in Atlanta, April 2024



Rob Walling | X



Derrick Reimer | X



Derrick Reimer



SavvyCal



Start Small Stay Small by Rob Walling



The SaaS Playbook by Rob Walling



Devin AI




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

Episode 708 | Outsourcing Marketing, Competitive Markets, and More Listener Questions (with Derrick Reimer)

In episode 707, Rob Walling, alongside guests Tracy Osborn and Einar Vollset, give their hot takes on some recent news in the world of SaaS. They discuss Once.com’s launch, liquidation preference nuances in startup buyouts, with moving from open source to full time income and more. 



Episode Sponsor:





Find your perfect developer or a team at Lemon.io/startups



The competition for incredible engineers and developers has never been more fierce. Lemon.io helps you cut through the noise and find great talent through its network of engineers in Europe and Latin America.



They take care of the vetting, interviewing, and testing of candidates to make sure that you are working with someone who can hit the ground running.



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And for subscribers of Startups For the Rest of Us, you can get 15% off your first 4 week contract with a developer by visiting lemon.io/startups



Topics we cover: 




2:18 - Once.com and the Implications of One-Time Software Sales



10:39 - Liquidation Preferences in Startup Acquisitions



21:59 - Turning an open source project into a business



24:32 - Book recommendations



30:30 - Is building a startup actually hard?



32:46 - Startups vs. lifestyle businesses




Links from the Show: 




Register for MicroConf US in Atlanta, April 2024



Once.com



Campfire



Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist by Brad Feld



Never Split the Difference by Chris Voss



The Anomaly by Herv Le Tellier



The Art of Learning by Josh Waitzkin



The Beginning of Infinity by David Deutsch



TinySeed



Einar Vollset (@EinarVollset) | X



Tracy Osborn (@itsTracyMakes) | TikTok




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 | Google

Episode 707 | Once.com, Open Source to FT Income, and More (Hot Take Tuesday)

In episode 706.5, join Rob Walling as he reconsiders some of his most common advice. He explores why lowering prices might make sense and discusses the benefits of a B2C business model. Rob also walks back his prior advice on bootstrapping two-sided marketplaces and launching multiple products to see what sticks. 



Topics we cover: 




1:04 – What would happen if you lowered prices?



3:56 – Benefits of a B2C approach



7:05 – Two-sided marketplaces allow to reach two audiences



8:47 – Launch a bunch of products to see what sticks



10:52 – This episode was released April 1, 2024




Links from the Show: 




The SaaS Playbook



Rob Walling (@robwalling) | X




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 | Google

Episode 706.5 | Rethinking My Most Common Advice

MicroConf US in Atlanta is here in just a couple weeks, and this is your last call to buy tickets. We've sold more than 90% of the tickets, and we will sell this event out as we have for many years. The event is April 21st through the 23rd in Atlanta, Georgia at the amazing Starling Atlanta. 



There are going to be 200-ish of your closest bootstrapped and mostly bootstrapped founder friends who are showing up to hear talks from folks like Rand Fishkin of SparkToro, Asia Orangio of DemandMaven. I'm giving a talk as well, and Dr. Sherry Walling will be talking about staying motivated as an entrepreneur.

We have a special guest MC, Lianna Patch, and we'll have a very special guest who has never appeared on the MicroConf stage before- Ben Chestnut, the co-founder of MailChimp.



Get all the details and secure your ticket before they run out at microconf.com/americas.

Episode 567 | From Developer to CTO to Buying the Company for $1

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