Jason Fried challenges your thinking on fundraising, goals, growth, and more

Dec 17, 2023 1h 49m 47 insights Episode Page ↗
This episode features Jason Freed, co-founder and CEO of 37 Signals, discussing his contrarian approach to building a profitable, bootstrapped business. He shares insights on why small teams, efficiency over growth, and gut instinct lead to more fulfilling and lucrative outcomes, challenging the typical venture-backed startup model.
Actionable Insights

1. Prioritize Business Independence

Make independence a foundational decision for your business, as it grants the freedom to operate exactly as you wish without external constraints or obligations to investors.

2. Focus on Profit, Not Revenue

Prioritize profit as your primary financial metric, understanding that high revenue doesn’t guarantee financial health, but consistent profit ensures sustainability and prevents going broke.

3. Embrace Constraints

Actively seek or impose constraints on your business, such as small teams and limited cash, as these limitations foster ingenuity, drive efficiency, and force effective problem-solving.

4. Explore Alternative Business Paths

Don’t default to the venture capital ‘go big or go home’ model; recognize that bootstrapping offers many more viable and often more fulfilling pathways to building a successful and sustainable business.

5. Define Success by Enjoyment

Measure success by asking if you genuinely enjoyed the work and would willingly do it again, prioritizing personal fulfillment and worthwhileness over external metrics or growth targets.

6. Play Infinite Games

Focus on playing ‘infinite games’ in business and life, pursuing endeavors that never end (like building relationships or a company you love) rather than finite goals (like exits or promotions) for greater long-term happiness.

7. Trust Your Gut Instinct

Value and utilize your gut and intuition as crucial decision-making tools, giving them credit for synthesizing vast amounts of known and subconscious experiences into valuable insights.

8. Avoid Long-Term Planning

Minimize rigid long-term planning to avoid making outdated decisions and committing to future obligations that can lead to unhappiness; instead, stay focused on the present and adapt as you go.

9. Reframe Work Metaphors

Consciously choose positive, additive language (e.g., ‘create,’ ’exist,’ ‘make something great’) over aggressive, destructive war metaphors in business to foster a mindset of pride, excitement, and creation.

10. Focus on “Stay Ups”

Shift your mindset from focusing on ‘startups’ to ‘stay ups,’ recognizing that sustaining a business long-term is much harder and more commendable than merely launching one.

11. Monitor Your Energy & Interest

Regularly assess if your business fuels or saps your energy; if it consistently drains you, re-evaluate its worth and consider changes to maintain personal and professional well-being.

12. Prioritize Efficiency Over Growth

Adopt a business model that prioritizes efficiency in operations and resource allocation over rapid, often unsustainable, growth, which can lead to ‘slop’ and unprofitability.

13. Simplify Product & Pricing

Streamline your product offerings to a single core product with simple pricing to reduce complexity, avoid high support costs, and eliminate the need for extensive sales and customization.

14. Underdo the Competition

Instead of trying to ‘outdo’ competitors (which is expensive and defensive), aim to ‘underdo’ them by offering more simplicity and clarity in your products and services.

15. Minimize Startup Expenses

Drastically reduce startup costs by avoiding non-essential expenses like branding, offices, or custom web design; instead, leverage affordable tools and self-service platforms.

16. Maximize Early Self-Reliance

In the initial stages of your business, strive to do as much work as possible yourself, delaying hiring until absolutely necessary to minimize costs and avoid the complexities of managing others.

17. Prioritize Business Simplicity

Actively pursue simplicity in all business operations, recognizing that while simple tasks can be challenging, complexity invariably leads to greater difficulties and can quickly overwhelm even small businesses.

18. Practice Negative Visualization

Mentally prepare for the worst-case scenario and make peace with potential failures, as this ’negative visualization’ allows you to move forward with greater confidence and less anxiety.

19. Adopt ShapeUp Development

Implement the ‘ShapeUp’ development framework, using fixed ‘appetites’ of no more than six weeks per feature instead of flexible time estimates, to streamline product building and prevent long-running projects.

20. Use Small, Time-Boxed Teams

Structure product development with small, cross-functional teams (e.g., one programmer, one designer) given a maximum of six weeks to deliver a feature, preventing scope creep and slow decision-making.

21. Empower Teams to Define Work

Empower development teams by providing a shaped idea rather than detailed specs or task lists, allowing them to define the specific work needed and figure out the implementation independently.

22. Set Fixed Time Appetites

Counter the tendency for work to expand by setting fixed ‘appetites’ (time budgets) for tasks, rather than open-ended estimates, to ensure efficient completion within set limits.

23. “Kill” Overdue Projects

If a project cannot be completed within its fixed time ‘appetite,’ be prepared to ‘kill’ it rather than extending the deadline, to maintain system integrity and prevent endless, demoralizing projects.

24. Implement “Cool Down” Periods

Schedule ‘cool down’ periods (e.g., two weeks) after intense work cycles, allowing teams to address minor tasks, fix bugs, or pursue small improvements, fostering replenishment and continuous refinement.

25. Avoid Firm Delivery Promises

Refrain from making definitive promises about project completion dates, particularly distant ones like ‘by the end of the year,’ as this often leads to disappointment and undermines trust.

26. Pilot New Methods on Low-Stakes Projects

When adopting new methodologies, start by applying them to low-criticality projects where failure has minimal impact, allowing your team to learn and improve without high stakes.

27. Avoid Rapid 180-Degree Changes

Do not attempt rapid, fundamental 180-degree changes in your business or processes, as existing organizational momentum makes such drastic shifts prone to failure.

28. Limit Failure Post-Mortems

Avoid excessive post-mortem analysis of failures, as the true causes are often complex and unknowable, and prolonged analysis can lead to superficial conclusions just for the sake of agreement.

29. Ask “How Does This Feel?”

Foster intuitive decision-making by encouraging open-ended discussions and asking team members ‘What do you think?’ or ‘How does this feel?’ to tap into their gut reactions and emotional responses.

30. Test Raw Instincts with Project

In hiring, especially for creative roles, assign a paid project and then ask candidates ‘If you had more time, what would you do?’ to assess their raw instincts, creativity, and ability to riff on the spot.

31. Embrace Ignorance for Innovation

Approach new challenges with a willingness to be ignorant of conventional methods, as not knowing ‘how it’s supposed to be done’ can foster greater creativity and reliance on intuition, leading to novel innovations.

32. Offer “Pay Once” Software

Explore developing and offering non-subscription, ‘pay once’ software products as an alternative to SaaS, addressing potential ‘subscription fatigue’ and providing value for a single purchase.

33. Target Overpriced Software Commodities

Identify ‘commodity’ business software categories where numerous similar products still charge premium subscription prices, as this presents an opportunity to offer a high-quality, lower-cost, non-subscription alternative.

34. Build Essential 80/20 Generics

Create high-quality, simple products that master the core 80/20 functionality, rather than attempting to replicate every feature of complex, expensive alternatives.

35. Seek Zero Marginal Maintenance Cost

Pursue business models, like self-hosted, one-time purchase software, that eliminate ongoing marginal maintenance costs associated with hosting and support, boosting profitability.

36. Offer Complementary Niche Tools

Develop products that serve as complementary tools or specialized solutions for specific contexts (e.g., backups, secure communication) rather than solely aiming to replace existing market leaders.

37. Target “No-Brainer” Price Points

Price your products to be an easy, ’no-brainer’ purchase for customers (e.g., under $1000 for business software), encouraging adoption as a valuable addition to their toolkit.

38. Provide Product Source Code

Grant users access to your product’s source code (with appropriate licensing) to empower them, especially product teams, to learn from its construction, modify, and customize it for their specific needs.

39. Design for Universal Accessibility

Design products for universal accessibility by minimizing text and focusing on intuitive categories people already understand, reducing the need for localization and making it instantly usable worldwide.

40. Implement Dynamic Multi-Language Panels

For global products, provide dynamic translation panels that display key words or phrases in multiple languages simultaneously, offering universal access without requiring separate language installations.

41. Embrace New Creative Explorations

Permit yourself to pursue novel creative projects and ideas, even if they diverge from established plans, to sustain excitement and personal engagement in your work.

42. Focus on Current Execution

Prioritize and concentrate on the tasks and projects currently underway, rather than being overwhelmed by a vast array of potential future opportunities.

43. Imagine an Alternate CEO

Periodically engage in the thought exercise of imagining how an outsider would run your business to identify potential missed opportunities or alternative strategies.

44. Seek New Business Grooves

Actively identify and explore new ways of operating or new opportunities to avoid getting stuck in established routines and to foster continuous evolution.

45. Hire Selectively for Small Teams

Maintain a small team size to foster close collaboration and allow for highly selective hiring, ensuring cultural fit and shared values.

46. Assess Candidate Tastes & Influences

During hiring for creative roles, inquire about candidates’ tastes, admired products, and influences to gauge their perspective and the unique contributions they might bring.

47. Seek Aligned VC Investors

If pursuing venture funding, seek out investors who align with a disciplined approach, understand your reluctance for growth obsession, and grant you the autonomy to build the business on your own terms.