Episode 787 | "We Shut Down a $1.5M Product, and Raised $10M Instead"
How do you know it’s time to move on from a product that’s growing?
In this episode, Rob Walling chats with Braden Dennis, co-founder of Fiscal.ai (formerly FinChat), about a rare founder journey: bootstrapping, catching lightning in a bottle, and choosing to go big with venture capital. They dive into the emotional and strategic weight of shutting down a $1.5M ARR product, what shifts when you scale past 40 people, and why Braden prioritized long-term vision over short-term revenue.
Topics we cover:
(2:30) – From FinChat to Fiscal.ai: rebranding and repositioning
(6:50) – Why they raised a $10M Series A
(13:09) – From bootstrapped to venture-backed: what changes?
(19:56) – Becoming a real CEO at 25 employees
(26:44) – Why they shut down a $1.5M product
(30:30) – Lessons from having four co-founders
(33:13) – The benefits of joining TinySeed
Links from the Show:
MicroConf Connect
The Great CEO Within
TinySeed: SaaS Institute
Fiscal.ai (formerly FinChat)
Braden Dennis (@BradoCapital) | X
Braden Dennis | LinkedIn
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 786 | Questions About Bootstrapping SaaS to a $90M Exit (with Kevin Wagstaff)
How do you really know when you’ve hit product-market fit?
In this episode, Rob Walling welcomes back Kevin Wagstaff, co-founder of Spectora, to answer listener questions about early traction in Facebook groups, finding product-market fit, handling criticism, and what it really took to bootstrap to a $90M exit.
Want to get your questions answered? Drop them here.
Topics we cover:
(3:15) – Early traction using Facebook groups
(7:17) – The tradeoff between growth and work-life balance
(12:26) – Participating inside Facebook groups run by rivals
(14:39) – Ranking for niche SEO terms
(19:06) – Funding the early days through consulting
(25:14) – Surviving churn in a seasonal, high-turnover market
Links from the Show:
SaaS Institute
Mark Cuban Blog Post
Kevin Wagstaff | LinkedIn
Kevin Wagstaff (@KevinWagstaff3) | X
Spectora
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
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Episode 785 | Choosing Between AI Products, Building Multiple Apps, and More Listener Questions (A Rob Solo Adventure)
How do you choose between multiple product ideas?
In this solo episode, Rob Walling answers listener questions about picking between two SaaS ideas, product positioning, and how to know when to stop working on a project.
Want to get your question answered? Drop them here.
Topics we cover:
(3:06) – Choosing between two AI products
(9:38) – Will early niche positioning hurt future growth?
(14:51) – At what point would you consider lowering prices?
(22:35) – Narrowing your ICP and product focus
(28:07) – How do you spec agency projects?
(30:10) – Should you keep building on a changing platform?
Links from the Show:
MicroConf Europe | Istanbul, Sep 28-30, 2025
SaaS Launchpad
TinySeed
The SaaS Playbook
MicroConf Connect
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
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Episode 784 | The Wealth Ladder: Six Levels of Financial Freedom
What’s the real roadmap to lasting financial freedom?
In this episode, Rob Walling chats with Nick Maggiulli about his new book, The Wealth Ladder. Nick explains how to identify your current financial stage and what it really takes to move up. They dig into how wealth changes your spending habits, why exits (not salaries) drive significant changes in net worth, and how your definition of freedom might evolve over time.
Topics we cover:
(6:07) – Defining the six levels of wealth
(11:49) – Why earning more isn’t enough
(14:17) – How entrepreneurs build wealth
(15:15) – The “0.01%” spending rule
(31:13) – Can money actually make you happier?
Links from the Show:
Invest in TinySeed
Of Dollars And Data
The Wealth Ladder by Nick Maggiulli
Just Keep Buying by Nick Maggiulli
The E-Myth Revisited by Michael E. Gerber
Nick Maggiulli | LinkedIn
Nick Maggiulli (@dollarsanddata) | 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
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Episode 783 | Bootstrapping ScrapingBee to $5M ARR and an 8-Figure Exit
When is the right time to sell your profitable SaaS?
In this week's episode, Rob Walling talks with Pierre de Wulf, co-founder of ScrapingBee, about how they mostly bootstrapped their web scraping SaaS to $5 million ARR and an eight-figure all-cash exit. They explore the pivotal shift that took them from $7K MRR to nearly $1M ARR in just 15 months, what Pierre splurged on post-exit, and the emotional, legal, and strategic complexities of selling a company.
Topics we cover:
(3:31) – Why they chose to sell
(5:41) – Post-exit emotions and celebrations
(9:57) – Lessons from failed startups before ScrapingBee
(13:16) – From 8k to $1m ARR in 15 months
(17:14) – Building a scalable SEO content engine
(29:19) – Handling a major cease-and-desist
Links from the Show:
MicroConf Connect
MicroConf Talk by Pierre de Wulf
The Java Web Scraping Handbook
ScrapingBee Blog
TinySeed
Discretion Capital
Pierre de Wulf (@PierreDeWulf) | X
Pierre de Wulf | LinkedIn
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
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.
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