Startups For the Rest of Us

Startups For the Rest of Us

Episode 795 | TinySeed Tales s5e4: The $20K Milestone

September 11, 2025

Achieving significant revenue milestones like $20K MRR can paradoxically trigger anxiety and a focus on future challenges rather than immediate celebration, highlighting the 'arrival fallacy' in entrepreneurship.

Episode 794 | From Struggling Side Project to Life-Changing SaaS Exit

September 9, 2025

Unexpected external events, like the pandemic, can dramatically shift market dynamics and create product-market fit for seemingly niche B2C products, even when founders are on the verge of giving up.

Episode 793 | TinySeed Tales s5e3: Building Momentum

September 4, 2025

Early-stage SaaS companies can achieve significant growth and attract larger deals by proactively investing in security and compliance measures like SOC 2, even if it seems like a tedious expense initially.

Episode 792 | Hot Take Tuesday: GPT-5 Struggles, the A.I. Bubble, and the Windsurf Debacle

September 2, 2025

TinySeed's first fund has returned more capital to investors than was initially invested, placing it in the top 10% or 5% of funds from its vintage, which is a significant achievement in venture capital given the long timelines for fund returns.

Episode 791 | TinySeed Tales s5e2: Growing Pains

August 28, 2025

Focusing on agencies as a customer segment has proven to be a low-friction, high-momentum strategy for Outbound Sync due to their deep understanding of the product's value proposition and their ability to integrate it into their own sales processes.

Episode 790 | From Scrappy to Scalable: Evolving Your Role as a Founder

August 26, 2025

A founder's role must fundamentally evolve as their company scales, transitioning from direct execution to architecting systems and setting context for others.

Episode 789 | TinySeed Tales s5e1: From Agency to SaaS

August 21, 2025

Transitioning from an agency to a SaaS business requires a significant mindset shift, moving from a service-based mentality to one focused on scalable product growth and strategic decision-making.

Episode 788 | Do I Need a Co-founder? And More Listener Questions (with Derrick Reimer)

August 19, 2025

Non-technical founders leveraging AI tools for rapid product development face significant risks regarding code security, maintainability, and scalability, making a technical co-founder or experienced developer crucial for long-term SaaS success.

Episode 787 We Shut Down A 1 5M Product And Raised 10M Instead

August 12, 2025

Venture funding can be a strategic tool to accelerate growth and compete in crowded, winner-take-most markets, even for companies that started bootstrapped.

Episode 786 | Questions About Bootstrapping SaaS to a $90M Exit (with Kevin Wagstaff)

Early-stage SaaS founders can achieve significant growth by relentlessly engaging with their target audience in online communities, even if it requires unglamorous work and a temporary sacrifice of work-life balance.

Episode 785 | Choosing Between AI Products, Building Multiple Apps, and More Listener Questions (A Rob Solo Adventure)

When choosing between passion projects with limited revenue and more commercially viable but competitive ideas, consider the personal calculus of whether the intrinsic value of the project outweighs the potential for success, and for bootstrapped founders, avoid significant regulatory hurdles.

Episode 784 | The Wealth Ladder: Six Levels of Financial Freedom

The 'Wealth Ladder' framework categorizes wealth into six levels based on net worth, with each level suggesting different financial strategies, spending freedoms, and life goals.

Episode 783 | Bootstrapping ScrapingBee to $5M ARR and an 8-Figure Exit

Bootstrapped companies often fail due to founder burnout rather than a lack of funds, highlighting the importance of founder motivation and knowing when to exit.

Episode 782 | Why I Succeeded: My 10 Best Entrepreneurial Decisions

Entrepreneurial success is built on a foundation of calculated risks, continuous learning from mistakes, and a willingness to embrace hard, unglamorous work.

Episode 781 | A Founder's Regret List: 12 Mistakes I’ll Never Make Again

True entrepreneurial success requires consistent action and decision-making with incomplete information, rather than solely relying on theoretical knowledge from books.

Episode 780 I Ll Never Sell My Company And Other Myths Founders Tell Themselves

Founders who believe they will never sell their company risk significant financial loss, as growth multiples on exits are heavily dependent on consistent growth, and flat businesses often yield much lower valuations.

Episode 779 | 10 Myths Most SaaS Founders Believe

Founders who have reached seven-figure ARR have likely already demonstrated marketing and sales capabilities, even if they don't identify as marketers or salespeople.

Episode 778 | Pricing Pilot Projects, Niching Down, Skipping Stairsteps, and More Listener Questions (A Rob Solo Adventure)

Entrepreneurship inherently involves calculated gambles, and the concept of 'de-risking' is better understood as having contingencies like pivoting or expanding market reach rather than eliminating risk.

Episode 777 | Why Retiring Might Be the Worst Goal for Entrepreneurs

Retiring at a traditional age like 65 may lead to unhappiness and a lack of purpose, as evidenced by the "unretirement" movement and the psychological benefits of meaning over mere happiness.

Episode 776 | How Bootstrapping Led to a Life-Changing $90M SaaS Exit

Bootstrapped SaaS companies can achieve significant valuations and exits by focusing on niche markets with underserved customer needs and prioritizing exceptional customer service and word-of-mouth growth.

Episode 775 | A.I. Coding Tools, User Experience, Racking Your Own Servers, and More Listener Questions (with Derrick Reimer)

AI coding tools significantly shorten MVP development time, but maintainability and catching AI-generated mistakes remain critical concerns for long-term viability.