"Don't waste your chips on bad hands."

Dimitar Stanimiroff has been through multiple exits, some successful, some painful shutdowns. He co-founded WePal (acquired) and Heresy (shut down after 3.5 years). His biggest financial return came from joining Stack Overflow, not founding his own company.

In today's episode, I'm joined by Dimitar Stanimiroff, a seasoned SaaS founder, operator, and investor who's experienced both sides of the exit coin. After co-founding WePal and seeing it acquired, he started Heresy, raised $1M in venture funding, and ran it for 3.5 years before making the difficult decision to shut it down. He then joined Stack Overflow as an operator and helped scale it, resulting in his biggest financial return to date.

Together we unpack:

• Why "quitting on time feels like quitting too early" and the real cost of staying too long
• How to think of your entrepreneurial journey like poker chips; finite resources you can't waste
• The hard reality of shutting down a business after raising venture capital
• Why his mentor Joel Spolsky told him to quit just months after launching
• When plateauing milestones become warning signs it's time to fold

👆 If you're a founder struggling with the decision to persevere vs. pivot vs. shut down, this conversation provides a framework for making one of the hardest decisions in business.

About Dimitar Stanimiroff

Dimitar Stanimiroff is a seasoned SaaS founder, operator, and investor. He co-founded WePal (acquired) and Heresy, and helped scale Stack Overflow, Handshake, and CrossBeam to over $100M ARR. As an angel investor in B2B SaaS, he's backed PatchHQ, Lightdash, and others from pre-seed to Series A. His biggest insight: think of your time as poker chips and don't waste them on bad hands.

Connect with Dimitar Stanimiroff on LinkedIn.

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"I had to let everyone go and run the entire business myself."

Tara Button's Buy Me Once had raised £3 million and grown to 14 staff. They were burning through cash faster than they could raise it. The choice: close the business completely or go solo with AI automation.

The result? Q4 2024 revenue exceeded Q4 2023 (with the full team) and they made their first profit ever.

In today's episode, I'm joined by Tara Button, bestselling author and founder of Buy Me Once, a mission-driven e-commerce business finding the longest-lasting products on the planet. When facing a critical cash crisis in 2024, Tara made the radical decision to let go of her entire 14-person team and rebuild the company using AI automation, despite having zero coding experience.

Together we unpack:

• How to identify which business tasks are truly critical (hint: it's less than you think)
• The step-by-step process she used to replace entire departments with automations
• Why she worked 16-hour days building email scrapers and inventory systems with ChatGPT
• How founders can start implementing AI automation without ripping everything up

👆 If you're a founder feeling overwhelmed by operational complexity or wondering whether AI can really replace human work, this conversation will open your eyes to what's possible.

About Tara Button

Tara Button is the founder of Buy Me Once, an e-commerce platform dedicated to finding the longest-lasting products on the planet to combat throwaway culture. After her business idea went viral in 2016, she raised over £3 million and authored the Amazon bestselling book "A Life Less Throwaway." When her business faced a cash crisis in 2024, she made the bold decision to rebuild it as a one-person operation using AI automation, resulting in their most profitable quarter ever.

Connect with Tara Button on LinkedIn.

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Why You Can't Sustain What You Don't Enjoy

Nick Baker left his successful consultancy after 25 years, burnt out from always being "on." He became a non-exec, convinced he'd never return to operational leadership. Then UK Padel came along, and he became CEO because he genuinely loved what they were building.

The lesson? You can endure anything temporarily, but you can't sustain what you don't enjoy.

About Nick Baker:

Nick is the CEO of UK Padel and former co-founder of Alpha FMC, which he took through private equity investment to a successful IPO. After spending 25 years in financial services and stepping back from executive roles, Nick found himself drawn back into operational leadership through his passion for racket sports and building something he truly believed in.

Together we unpack:

• Why genuine passion for your business isn't just nice-to-have; it's essential for long-term success
• How to know when it's time to step away and make yourself redundant the right way
• The secret to staying authentic as you scale (hint: stay involved in delivery)
• Why founder-led selling works so well and how to maintain that edge

👆 If you're a founder feeling disconnected from your business or wondering how to sustain your energy for the long journey ahead, this conversation will give you clarity.

About Nick Baker

Nick Baker is the CEO of UK Padel, which operates multiple padel clubs across the UK and runs the country's biggest national tournaments. He previously co-founded Alpha FMC, a financial markets consultancy that he grew over 25 years before taking it through private equity investment to a successful IPO. Nick is also an active angel investor, having backed over 75 startups, and serves as chairman for several businesses.

Connect with Nick Baker on LinkedIn.

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