As the year winds down, I find myself reflecting on this crazy entrepreneurship journey of Overwrite and the lessons I’ve gathered along the way. Here are 24 lessons I picked up over time. Each has shaped I think about business, and I hope sharing them will inspire and guide others.
Industry Lessons
Choose Your Market Wisely: You cannot extract significant value from a small market. Even an average company can thrive in a massive market, while exceptional ones may struggle in a niche. Overwrite began with a focus on CDFIs, but we’ve since expanded to the broader economic development sector. This shift has opened new opportunities and reinforced the importance of aligning our vision with a market that can sustain it.
Solve Hard Problems: The most valuable opportunities often lie in solving difficult problems that others shy away from. Tackling these challenges not only differentiates you from competitors but also increases the value you bring to the table. Easy solutions attract many players, diluting their worth. Embrace the hard path—it’s where innovation lives.
People Are Watching: Even when it feels like no one is paying attention, they are. Social media engagement and emails don’t always reflect the impact of your work. Stay consistent, act with integrity, and trust that your efforts are being noticed, even if silently.
Company Lessons
Have a Strong “Why”: Your “why” is the anchor that holds your business steady when distractions and challenges arise. It shapes your mission and fuels your decision-making. Whenever momentum builds or uncertainty creeps in, revisiting your purpose can guide your path.
Do It Afraid: There will never be a perfect time to take the leap. Fear and self-doubt are inevitable companions on this journey, but they shouldn’t paralyze you. Move forward despite them. Growth lies on the other side of fear.
Good Things Take Time: Success rarely happens overnight. Anecdotally, it takes about five years for a business to shift from outbound efforts to a steady stream of inbound opportunities. Patience and persistence are your allies—stay the course, and let time work its magic.
Pivot Fast, Pivot Often: Adaptability is crucial in the early stages of a business. Pivoting doesn’t mean abandoning your vision but refining how you achieve it. Whether it’s your product, marketing, hiring, or pricing, be open to change while staying true to your core mission.
Entrepreneurship Is Hard: Starting a company demands more than expertise—it requires resilience and adaptability. Many entrepreneurs underestimate the challenges of sales, operations, and team management. It’s okay to reassess your path and pivot toward what works best for you, even if that means stepping back into a role within a larger organization.
Celebrate Your Wins: Pause to acknowledge milestones, big or small. Celebrating progress energizes your team and reminds you of how far you’ve come. Document these moments—they’ll serve as motivation during tougher times.
Operational Lessons
Keep Things Simple: Customization is the enemy of scale. Standardize processes wherever possible and avoid reinventing the wheel. Many operational challenges have already been solved—leverage existing solutions and focus your energy on what truly matters.
Product Lessons
Choose Your Product or Service Wisely: Products generally fall into two categories: mass-market with low margins or bespoke with high margins. Early on, Overwrite made the mistake of combining the two. We’ve since shifted to streamline underwriting and technical assistance while reserving bespoke efforts for consulting. Clarity in product strategy ensures profitability and efficiency.
Hiring Lessons
You Cannot Outsource Hiring: As a founder, your involvement in hiring decisions is non-negotiable. While HR teams can assist with logistics, you must ensure alignment between your company’s needs and the people you bring on board. Building the right team is one of your most critical responsibilities.
You Can’t Teach Everything: Some qualities like ambition, self-motivation, and passion cannot be taught. Not every employee needs to aspire to leadership, and that’s okay. Value those who excel in their roles, even if they prefer to stay in their lane.
Practice Radical Candor: Giving clear, honest feedback while showing personal care for your team is essential. Avoiding difficult conversations may feel easier in the short term but often leads to bigger problems. Embrace the philosophy of Radical Candor; it strengthens teams and fosters trust.
Sales Lessons
Not All Money Is Good Money: It’s okay to say no to a contract that doesn’t align with your values or expertise. Even if the opportunity seems lucrative, trust your instincts. Ethical concerns, misalignment with your core business, or gut feelings are valid reasons to walk away.
Listen: Pay attention to what customers want, both in words and actions. Observe where they spend their time and money. If something isn’t selling, take it as a signal to adapt or let go of your ego and refine your offerings.
Follow the Numbers: Revenue patterns reveal where to focus your efforts. For example, I noticed that historically, 58% of Overwrite’s revenue came from Colorado-based clients. This insight prompted me to reevaluate how we allocate time and resources. Data doesn’t lie so use it to guide your strategy.
Relationships Are Key: Expertise opens doors, but relationships often hold the key. Nurturing connections is as vital as refining your craft. Relationships have the power to create opportunities that might otherwise remain out of reach.
Don’t Take It Personally: Sales comes with rejection. Learn to accept “no” without holding grudges or taking it to heart. Stay open-minded, even toward those who may have doubted you in the past.
Self-Development Lessons
Put Yourself Out There: Growth doesn’t happen in your comfort zone. True learning comes from stepping into unfamiliar situations and embracing the discomfort of the unknown. Challenge yourself to explore, question, and grow.
Financial Lessons
Have a Budget: A solid financial foundation begins with budgeting. Track performance closely and ensure you understand the numbers driving your business.
Losing Money Is not a strategy: Every service or operation must generate profit. Small businesses can’t afford loss leaders. Strive to make each offering sustainable, even if the margins are small.
Time Management Lessons
Protect Your Time: As your business grows, more demands will compete for your attention. Learn to say no, prioritize emails over unnecessary meetings, and guard your schedule. Time is your most valuable asset so spend it wisely.
Know What You Like: Lean into what you enjoy and excel at. Delegate the rest to others within or outside your organization. This not only enhances efficiency but also brings joy to your work.
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