Startups For the Rest of Us

Latest Episodes:

Episode 613 | Hacking Your Founder Psychology Jul 26, 2022

Show notes

In episode 613, Rob Walling chats with Dr. Sherry Walling about the release of her new book, Touching Two Worlds: A guide for finding hope in the landscape of loss. They cover a lot in this episode, including the hustle of launching a book, the behind the scenes of how Sherry has hacked her own psychology to help promote the book, and grief in entrepreneurship.

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Topics we cover:

[4:04] What it is like to publish a book with a traditional publisher

[5:30] The process of launching and promoting a book

[9:24] A clever way to reframe cold outreach

[15:52] Hacking your founder psychology

[21:03] A short book summary

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 612 | Balancing a Side Project and Going Full-time on Your Product Jul 19, 2022

Show notes

In episode 612, Rob Walling chats with longtime friend and repeat podcast guest Dave Rodenbaugh. Dave was even at the very first MicroConf back in 2011.

In this episode, we have a candid conversation on our experiences balancing side projects with a day job, struggling with the decision in our own different ways of when to quit, and the surprising habits you have to unlearn once you are finally independent of the day job and consulting work.

Topics we cover:

[1:27] Dave’s thought process behind expanding Recapture

[5:34] The decision to go full-time on Recapture

[15:05] Dave’s process for unlearning bad employee / consultant habits

[20:07] The danger of the arrival fallacy

[24:20] What would you do if you sold the business?

[26:03] Balancing a side project with your day job

Links from the Show:

Dave Rodenbaugh (@DaveRodenbaugh) I Twitter
Recapture
Rogue Startups

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 611 | Bootstrapping ProfitWell to a $200M Exit (with Patrick Campbell) Jul 12, 2022

Show notes

In episode 611, join Rob Walling as he chats with Patrick Campbell, the cofounder of ProfitWell, on how he and his co-founders bootstrapped ProfitWell to a $200 million exit.

Profitwell was acquired by Paddle earlier this year. We dive into a bunch of topics you have not heard elsewhere, including details about the actual transaction, what was the stock vs. cash split, the revenue breakdown of consulting versus SaaS when they sold as well as talking through his thought process as they were deciding whether to sell.

Topics we cover:

[3:53] Using their consulting business to fund and grow Profitwell in the early days

[8:23] The split between cash and stock in Profitwell’s acquisition

[9:49] The percentage of Profitwell’s revenue from consulting vs. SaaS

[13:39] The conversations that Patrick and his cofounders had from the get-go about their end goals and how much to reinvest in the business

[15:02] The ownership split between all of the cofounders

[17:08] How he made sure his employees were taken care of in the acquisition

[19:05] Did Patrick ever consider taking funding?

[26:14] How long it took to sell the business from the first contact with Paddle

[31:55] Why should SaaS founders take money off the table once they hit certain milestones?

[36:01] Patrick’s feelings about competing with Stripe

[42:15] Why Patrick moved to Puerto Rico

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 610 | How I Would Start Over Today, Bad Habits of Solopreneurs, and the Benefits of a Day Job (A Rob Solo Adventure) Jul 05, 2022

Show notes

In episode 610, join Rob Walling for a solo adventure where he talks about the benefits of working a day job before launching your company, some bad habits he picked up in the early days, why the college dropout narrative is annoying, and what he would do if he was starting over today.

Topics we cover:

[1:08] The benefits of working a day job

[6:20] Some bad habits Rob learned as a solopreneur in the early days

[9:45] Why the college dropout narrative is bs

[12:51] What would Rob do if he was starting over today

[19:22] The benefits of starting a business today vs. 10 years ago

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 609 | Building Your MVP, the Bug Fix Hamster Wheel, and More Listener Questions Jun 28, 2022

Show notes

In episode 609, join Rob Walling for a solo adventure as he answers a handful of listener questions ranging from when it makes sense to have multiple LLCs and hiring task-level vs. project-level thinkers to planning for large projects. He also shares his thought process behind ways you can build a complex mobile app prototype in a capital efficient manner.

Topics we cover:

[1:56] Is it worth it to create multiple LLCs?

[6:10] Do you have any tips for how to find the time to work on future improvements when it feels like you don't have time to do anything but fix bugs and answer support tickets?

[13:01] Do you have any advice around how to build a complex mobile app MVP in a capital efficient manner?

[20:30] Should internal company, marketing and transactional emails be on the same domain?

[22:27] How do you plan for a large project?

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 608 | Bootstrapping (and Exiting) a 7-Figure Info Product Jun 21, 2022

Show notes

In episode 608, Rob Walling chats with Adrian Rosebrock, who bootstrapped and successfully exited his seven-figure info product company, PyImageSearch, in 2021. PyImageSearch provided digital courses around visual image detection and image classification in Python.

Adrian wasn’t always an entrepreneur. He graduated with a PhD in computer science, got a day job, realized early on that he hated it, and just stair-stepped his way up to running a successful business. In this episode, we cover a lot including Adrian’s decision to start blogging and launch a Kickstarter campaign in the early days to learning how to hire employees and making the decision to sell the business in 2021.

Episode Sponsor:

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Topics we cover:

[2:41] The story of how Adrian first discovered MicroConf

[6:29] Why Adrian didn’t want to go down the traditional path after getting his PhD in computer science

[10:01] When he knew having a traditional day job as an employee wasn’t for him

[11:24] How he used the stair-step approach to launch PyImageSearch

[13:54] What Adrian did when he started to see early traction

[16:45] Did having a PhD in computer science have a big impact in the early days of launching his business?

[18:05] Adrian’s approach to learning how to market

[20:31] How he balanced working a day job and his side business in the early days

[23:39] Adrian’s launch plan for selling his first ebook in 2014

[28:48] The epiphanies that Adrian had in the early days to keep plugging away

[33:33] How he went from making $38,000 in 2014 to $600,000 in 2016 as a company of one

[36:28] The mindset shifts he had to make when he started hiring employees

[39:10] Adrian’s decision to sell the business

[45:03] His reflections after selling the business in 2021

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 607 | Overcoming Plateaus, Stealth Launches, Founder-Driven Sales, and More Listener Questions Jun 14, 2022

Show notes

In episode 607, Rob Walling chats with Asia Orangio, and they answer listener questions about customer onboarding videos, overcoming revenue plateaus, stealth launches, and founder-driven sales.

Topics we cover:

[1:12] Where’s the best place to put customer onboarding videos?

[5:37] How to scale a content business

[15:36] What to do if revenue has plateaued?

[21:41] When to do a stealth launch

[26:30] Is it possible for a SaaS product to sell to the enterprise without a dedicated sales team?

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 606 | The Podcasting Landscape, Keeping Your Saw Sharpened, and Scaling Your Team with Craig Hewitt Jun 07, 2022

Show notes

In episode 606, Rob Walling chats with Craig Hewitt, the founder of Castos. They talk about company building, staying up to speed when you are no longer doing the day-to-day tasks as well as their thoughts on a recent string of acquisitions happening in the podcast ecosystem.

Topics we cover:

[1:24] 2 MicroConf Local events happening in Chicago and Denver

[3:50] The pros and cons of Spotify acquiring a couple of podcast analytics platforms

[7:51] The specific challenges with podcast analytics

[12:39] Spotify vs. Apple

[16:31] Staying up to speed as CEO once you have a team doing the day-to-day tasks

[28:32] Implementing OKRs at Castos

[33:07] Castos’ Mission

Links from the Show:

Craig Hewitt (@TheCraigHewitt) I Twitter
Castos
MicroConf Local
Seeking Scale
Rogue Startups
Bootstrapped Web
Tempo I Castos

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 605 | Building a SaaS with Little Dev Experience, Using No Code for Your MVP, Bootstrapping a Two-Sided Marketplace, and More Listener Questions May 31, 2022

Show notes

In episode 605, Rob Walling is joined by Ruben Gamez, and they dig into a handful of listener questions. Topics range from building a SaaS with little development experience and using no-code tools to build your MVP to stair-stepping bootstrapping a two-sided marketplace.

Topics we cover:

[0:55] Selling to the enterprise

[4:31] What level of development expertise would you say the founders of a B2B SaaS should have in order to create a successful product?

[13:26] Should you launch a productized service to validate a SaaS idea before building it?

[20:47] Can you use the stairstep method to bootstrap a two-sided marketplace business?

[31:34] Is no-code something you see mainly for building an MVP, or is it something that you could sustainably build an actual SaaS startup on without running into scaling issues? What are the downside risks to no-code tools other than platform risk?

[37:08] Do you think no-code tools will ever get to the point where you can build a full SaaS business?

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 604 | How to Decide Which Features to Build (with Derrick Reimer) May 24, 2022

Show notes

In episode 604, Rob Walling talks with Derrick Reimer and gets the latest update on SavvyCal, how he makes product decisions, and they also share the best things they’ve bought for $100 and $1000 that have added much more value to their lives than the price point.

Topics we cover:

[4:50] Apple’s influence on startup founders

[8:52] SavvyCal’s new Squadcast integration

[12:51] Some upcoming features in the works for SavvyCal

[14:05] Experimenting with a freemium feature—meeting polls

[17:07] Derrick’s mental framework for deciding what features to build next

[23:58] Switching from an employee to a founder mindset

[25:56] Would you rather fight one duck-sized horse or a thousand duck-sized horses?

[27:25] The best purchase Derrick has made for under $100 in the last 6 months

[33:14] The best purchase Derrick has made for under $1000 in the last 6 months

Links from the Show:

Derrick Reimer (@DerrickReimer) I Twitter
SavvyCal
Squadcast

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