Four-time entrepreneur Jason Cohen discusses startup ideas including optimizing social media replies, simplifying data tools, and targeting niche markets. The conversation explores using AI in strategy, choosing the right niche for startup success, and the role of personal strengths in competitive advantage.

Jason Cohen’s talk “Designing the Ideal Bootstrapped Business” from 2013 is a classic in the bootstrapper canon. In this episode, Jason joins Adam and Ben to see how the talk holds up a decade after its creation. Timestamps00:00 Intro00:27 Designing the ideal bootstrapped business06:53 Recurring revenue vs one-off sales13:30 Getting all the LTV up front18:31 Product validation24:56 Creating a cash machine26:05 Where does growth come from?41:25 Annual prepays46:41 Increasing your prices51:56 What new advice is there since this talk?59:00 What about freemium?01:03:39 What happens next?01:08:58 Picking an idea that's compatible with the life you want to live01:12:16 Ideas for TailwindLinksAdamBenJason

Jason Cohen shares his experiences of founding two unicorns valued at over $1 billion. Discusses the dilemma of choosing between being rich or king, the importance of purpose in company success, decision-making based on financial thresholds, navigating criticisms after selling a company, and nurturing success through good product taste and capable leadership.

Jason Cohen, co-founder of WP Engine and a 2-time unicorn founder, shares his startup wisdom at all stages of growth. Topics covered include scaling, funding, WordPress growth, dealing with people challenges at scale, fitting writing into his schedule, and his thoughts on Lemon Squeezy's growth and fundraising. Cohen also discusses the future of WP Engine and gives advice on identifying growth opportunities and understanding the customer base.

Jason Cohen, founder of Gastrograph, discusses using AI to understand flavor profiles in beer and food products. Topics include predicting consumer tastes, personalizing products with AI, and envisioning a future of AI-crafted products for shared experiences.

Eric Siu interviews Jason Cohen, the mind behind WP Engine, discussing bootstrapping a billion-dollar company, embracing optionality in business strategies, continuous customer development, creating a company culture for personal growth, hiring and accountability in management, and finding a niche in the AI landscape.

Interview with Jason Cohen about bootstrapping software companies, reaching $10k/month revenue, lies founders tell themselves, and why you may not follow advice. Emphasis on navigating founder challenges, building profitable self-funded business models, validating ideas, and breaking from conventional wisdom in entrepreneurship.

Exploring the conflict between pursuing wealth and personal fulfillment in entrepreneurship, Jason Cohen reflects on selling his business and the unexpected criticism he faced. The podcast delves into the emotional landscape of selling a business, contrasting profits with personal values, and the intertwining of ego, money, and freedom in entrepreneurship.

Two-time unicorn founder Jason Cohen shares insights on aligning startup with personal interests, tailoring business models to fit life stages, and considering long-term goals for better decisions. Emphasizes self-knowledge for a meaningful founder career.

Jason Cohen, founder of WP Engine and Smart Bear, shares unconventional insights on building billion-dollar companies without venture capital. Topics include embracing optionality in business strategies, operating like a public company, continuous customer development, creating a company culture for personal growth, and finding a niche in the AI landscape.