3 Lessons in 3 Years: what we’ve learned about supporting entrepreneurs

This month, Overwrite turns three. Over the past three years, we’ve had the privilege of walking alongside entrepreneurs from all walks of life. From first-time founders to seasoned business owners ready to scale. Our work has taken us into coffee shops, co-working spaces, and more than a few Zoom calls. We’ve seen the highs, the lows, and everything in between. And in that time, a few lessons have stood out as constants in the world of entrepreneurship. Lessons that shape how we deliver support through our technical assistance services and beyond. Here are three of the biggest lessons we’ve learned.

Lesson 1: Flexibility is the real secret ingredient

One of the first things we realized is that entrepreneurs work on their own clock. Sometimes that clock says 7AM. Sometimes it says 7PM. And sometimes it says, “I have a meeting in 15 minutes, but I really need to talk now.” Supporting entrepreneurs means adapting to their rhythms and not expecting them to conform to ours. That’s why our TA services are designed to meet business owners where they are. Whether it’s helping refine a loan application, creating a financial plan, or walking through compliance requirements step-by-step, we make sure the timing, format, and approach work for them.

Our takeaway: Flexibility isn’t just nice to have; it’s essential. The best support happens when we meet entrepreneurs on their terms, without adding more barriers to their already full plates.

Lesson 2: Small conversations can lead to big breakthroughs

We’ve learned that when an entrepreneur says, “I have a quick question,” what follows may not be quick, but it’s often important. Those conversations sometimes start with a small question about a spreadsheet or a marketing plan, and end with a breakthrough about how to restructure a business or approach a new market. This is why we build space for open-ended dialogue into our TA services. Entrepreneurs need room to think out loud, test ideas, and ask questions without fear of judgment. Sometimes our role is to provide an answer. Other times, it’s to ask a better question in return.

Our takeaway: Big shifts often grow from small moments. Listening deeply is just as valuable as providing solutions.

Lesson 3: Celebrate every step forward

In three years, we’ve celebrated big wins- clients expanding their retail footprint, hiring staff, being ranked higher in the app store, or securing major funding. However, we’ve also learned to celebrate the smaller steps. Entrepreneurship can be exhausting, and progress isn’t always linear. That’s why we make it a point to acknowledge when a business owner completes a milestone, even if it seems minor. Maybe they finally feel confident reading their own financial statements, or they took the leap to register their LLC after years of hesitation. These are victories worth recognizing because they build momentum.

Our takeaway: Encouragement fuels resilience. The more we highlight progress, the more likely entrepreneurs are to keep pushing forward, and that persistence is often the difference between success and burnout.

Three years in, our biggest realization is that supporting entrepreneurs isn’t just about resources. It’s about relationships. Our TA services are built on the belief that with the right guidance, timely information, and consistent encouragement, entrepreneurs can overcome challenges that once felt impossible. As we move into our fourth year, we’re excited to continue offering one-on-one technical assistance to help business owners strengthen their foundations, access funding, and build sustainable growth strategies. To all the entrepreneurs we’ve worked with so far: thank you for trusting us with your vision. And to those we haven’t met yet: we’re ready when you are. Here’s to the next three years of building, learning, and growing...... together.

P.S. If you’re a Colorado-based entrepreneur or know one who could use free, one-on-one guidance in areas like sales, hiring, accounting, and more, we’d love to connect.

Because when it comes to building a business, two heads really are better than one.

Just fill out our quick intake form, and we’ll be in touch.