Lost and Founder

1. Embrace transparency and vulnerability to build trust and improve team performance

If people have to cry in the bathroom, you're fucking up.

Psychological safety is crucial for team success. Research shows that teams with high psychological safety outperform those without it. This means creating an environment where team members feel comfortable expressing personal issues, sharing mistakes, and speaking up without fear of harsh criticism or judgment.

To foster psychological safety:

• Encourage open communication about work and personal challenges
• Lead by example, sharing your own vulnerabilities and mistakes
• Recognize and reward honest feedback and constructive criticism
• Create opportunities for team bonding and personal connections

By embracing transparency and vulnerability, you build trust, improve team cohesion, and ultimately drive better performance and innovation.

2. Focus on core strengths instead of diversifying prematurely

Great companies are almost universally fed by a powerful, ongoing set of marketing processes that earn attention from the right audiences and bring them to the company's (physical or virtual) doorstep.

Resist the temptation to diversify too quickly. Many startups make the mistake of expanding into multiple products or markets before establishing a strong foundation in their core offering. This can lead to diluted focus, stretched resources, and diminished quality across all offerings.

Instead:

• Identify your company's unique strengths and core competencies
• Double down on improving and expanding your primary product or service
• Build a strong brand and customer base in your core market
• Only consider diversification when you've achieved significant traction and have excess resources

By maintaining a laser focus on your core strengths, you can build a solid foundation for future growth and expansion.

3. Prioritize customer retention over acquisition for sustainable growth

Subscriber retention versus customer acquisition.

Retention is key for sustainable growth, especially in subscription-based businesses. While acquiring new customers is important, retaining existing ones is often more cost-effective and leads to higher lifetime value.

To improve customer retention:

• Invest in product quality and user experience
• Implement a customer success program to help users get the most value
• Regularly collect and act on customer feedback
• Create loyalty programs or incentives for long-term customers
• Focus on solving customer problems and delivering consistent value

By prioritizing retention, you can build a more stable revenue base and reduce the pressure to constantly acquire new customers, leading to more sustainable growth over time.

4. Understand the venture capital model and its implications before raising funds

Personal happiness and successfully raising venture capital are rarely correlated.

Venture capital is not suitable for every startup. The VC model typically requires rapid growth and a large exit (acquisition or IPO) to generate returns for investors. This can create pressure to scale quickly, sometimes at the expense of profitability or long-term sustainability.

Before seeking venture capital, consider:

• Your growth aspirations and willingness to aim for a large exit
• The potential loss of control and decision-making power
• Alternative funding sources (bootstrapping, angel investors, crowdfunding)
• The impact on company culture and employee expectations

If you do decide to raise VC funding, be prepared for the pressures and expectations that come with it, and ensure your goals align with those of your investors.

5. Develop a scalable marketing flywheel rather than relying on growth hacks

Growth hacks alone can't solve all your marketing problems, but the right ones may add immense value to an already humming marketing flywheel.

Build a sustainable marketing engine. While growth hacks can provide short-term boosts, they often don't lead to long-term, sustainable growth. Instead, focus on creating a scalable marketing flywheel that consistently attracts and converts customers.

Elements of a strong marketing flywheel:

• Content marketing that addresses customer pain points
• SEO to drive organic traffic
• Social media engagement and community building
• Email marketing for nurturing leads and retaining customers
• Referral programs to leverage word-of-mouth
• Continuous optimization based on data and customer feedback

By developing a comprehensive marketing strategy that builds upon itself over time, you create a more predictable and sustainable growth model for your business.

6. Create a dual career track to retain top individual contributors

There is a deeply held misconception in business culture that people management is (a) the only way to lead and (b) the only way to advance one's career.

Value individual contributors equally to managers. Many companies lose top talent by forcing skilled individual contributors (ICs) into management roles for career advancement. Create a dual career track that allows ICs to progress in title, compensation, and influence without becoming people managers.

Benefits of a dual career track:

• Retains top technical talent who may not excel in or desire management roles
• Allows employees to focus on their strengths and passions
• Provides diverse career options for employees
• Ensures management roles are filled by those with genuine interest and aptitude

Implement this by creating parallel advancement paths for ICs and managers, with equivalent levels of recognition, compensation, and influence at each stage.

7. Invest in self-awareness and behavioral change for personal and professional growth

When you find a real truth about yourself, or a truth about your company, it's going to have that same feeling. The truths we hide about ourselves and our creations stay secret because we bury them in layers of guilt and shame, of fear and self-loathing.

Self-awareness is a superpower. Developing a deep understanding of your strengths, weaknesses, motivations, and blind spots is crucial for personal and professional growth. This self-knowledge allows you to make better decisions, build stronger relationships, and lead more effectively.

To improve self-awareness:

• Seek regular feedback from peers, mentors, and subordinates
• Practice mindfulness and reflection
• Keep a journal to track thoughts, emotions, and patterns
• Work with a coach or therapist to uncover deeper insights
• Be open to challenging your own assumptions and beliefs

Remember that self-awareness is an ongoing journey, not a destination. Continuously invest in understanding yourself and your impact on others to become a more effective leader and individual.

8. Balance product development between minimum viable and exceptional

Great products are rarely "minimally viable".

Find the sweet spot between minimum viable product (MVP) and exceptional viable product (EVP). While the lean startup methodology emphasizes rapid iteration and learning through MVPs, launching a subpar product can damage your brand and make it harder to gain traction.

Considerations for product development:

• Start with a small, well-executed core feature set
• Gather feedback from trusted advisors and potential customers
• Iterate based on user feedback, but don't rush to launch prematurely
• Ensure your product solves a real problem better than existing solutions
• Balance speed to market with quality and user experience

Aim to create a product that is both viable and impressive enough to generate positive word-of-mouth and retain early adopters.

9. Consider early acquisition offers seriously, weighing pros and cons

Twenty-five million dollars.

Evaluate acquisition offers carefully. While the startup culture often glorifies building unicorns and going public, early acquisitions can provide significant benefits for founders, employees, and investors. Don't dismiss acquisition offers without careful consideration.

Factors to consider when evaluating an acquisition offer:

• Personal financial goals and life circumstances
• The potential for future growth versus current valuation
• Impact on employees and their career prospects
• Market conditions and competitive landscape
• Alignment with your long-term vision for the company
• The acquirer's culture and plans for your product/team

Remember that turning down an acquisition offer doesn't guarantee a better outcome in the future. Weigh the risks and rewards carefully, and be open to opportunities that could provide a positive outcome for all stakeholders.

10. Recognize and combat depression in entrepreneurship

Depression was a catalyst for me to seek professional therapy and professional coaching, something I hadn't done previously in my career.

Mental health matters. Entrepreneurship can be an emotionally challenging journey, often leading to stress, anxiety, and depression. Recognizing the signs of depression and taking proactive steps to address mental health is crucial for both personal well-being and business success.

Strategies for maintaining mental health:

• Seek professional help through therapy or coaching
• Build a support network of fellow entrepreneurs and mentors
• Practice self-care through exercise, meditation, and hobbies
• Set boundaries between work and personal life
• Be open about mental health struggles with trusted team members
• Focus on behaviors and habits, not just outcomes

Remember that seeking help is a sign of strength, not weakness. By prioritizing mental health, you'll be better equipped to handle the challenges of entrepreneurship and lead your team effectively.

Last updated: January 24, 2025