Written by Donna Harris, Founder & CEO of Builders + Backers.
It’s my birthday this week and, as we often do at key life milestones, I’ve been reflecting on my entrepreneurial journey. Twenty-plus years and six startups (plus dozens of investments and thousands of founders mentored). Each company was like a new version of myself as a builder – learning, iterating, evolving.
We talk about entrepreneurship in very short-term ways: funding announcements, rapid growth, how quickly we can scale and exit. For me, it’s been a long game. Many companies. Many chapters. Constant evolution.
I’m nothing like the V1 entrepreneur I was in my twenties. I’m older, wiser, and entirely more confident in my abilities and in what I’m building now.
Here are six gifts from me to founders everywhere – one hard-won lesson from each version of my journey.
Gift #1: The Power of Just Starting
My first startup was a services company in my twenties. I had no idea what I was doing – no business plan, no clear strategy, barely understood the fundamentals of running a company. But I jumped in anyway. Over time, I managed to drive some revenue, learned how to sell, and figured out operations on the fly, ultimately building a $1M business. But it was hard to scale beyond that, and I quickly realized the difference between a services business and a scalable product company. It was the classic services business hamster wheel – selling enough to keep the staff busy, having enough staff to service the business, but never getting ahead.
Ultimately I moved on from this company to Startup #2. But those few years of real-world startup experience taught me more about entrepreneurship than any number of entrepreneurship books or business school classes ever could have.
The Gift: Stop waiting to know what you’re doing. Start anyway.
“Sometimes you win. Sometimes you learn.” That first company was my “starter company” and the lessons I learned mattered more than the outcome. Most entrepreneurs never start because they think they need to figure it all out first. You don’t. The doing is the learning.
Gift #2: Know Your Real Boss
Startup #2 was my baptism by fire into venture capital. This was peak “dot-com era.” Money was flowing like water, and everyone believed the internet would change everything overnight. We raised loads of capital and suddenly found ourselves under crushing board pressure to grow at breakneck speed.
The investors had one obsession: get big fast and exit before the music stopped. Everything else became secondary. We hired bodies faster than we could onboard them, throwing people into roles without training or clear processes. The office buzzed with activity, but it was chaotic energy – people working harder, not smarter. Culture wasn’t even a consideration; it was just whatever emerged from the frenzy.
What we were building mattered less than how quickly we could scale it. Customer satisfaction, sustainable operations, building something people actually needed – these became nice-to-haves in service of the metric that mattered most: growth. The result was a dysfunctional organization where conflict became the norm and everyone was pulling in different directions.
The Gift: Understand whose vision you’re building toward – the investors’ quick exit or your long-term mission.
This experience taught me that VC money comes with strings attached, and those strings can strangle your company if you’re not careful. When external pressures override your internal compass, you stop building a business and start building someone else’s financial instrument. The hardest lesson? Sometimes the people writing the checks care more about their timeline than your success.
Gift #3: Two Rights Don’t Make Success
Startup #3 felt like we were finally doing everything right. We were a team of experienced builders who’d learned from our previous mistakes. We did proper customer interviews, validated the problem, and built something people genuinely wanted. The cloud was emerging, SaaS was revolutionary, and we were riding the wave of technological innovation.
But “doing everything right” turned out to be insufficient armor against reality.
Our customers loved what we built – they just couldn’t pay for it. What seemed like a slam-dunk market turned out to be full of organizations with good intentions and empty budgets. We spent a lot of time pivoting to find customers who actually had purchasing power, burning through resources and momentum. Then 9/11 hit, freezing the entire economy overnight. Enterprise spending disappeared. Budgets that existed in September were gone by October.
The final blow came when our primary investor died unexpectedly. What should have been a straightforward next funding round became a nightmare as his estate unraveled our capitalization table. We watched helplessly as circumstances completely beyond our control dismantled what we’d worked so hard to build.
The Gift: Product-market fit AND timing must both align. Sometimes you can do everything right and still fail.
This remains one of the most painful experiences of my entrepreneurial life, but it taught me that failure isn’t always about what you did wrong. Sometimes the market timing is off. Sometimes external forces intervene. Sometimes the perfect storm hits and even great companies get swept away. The hardest lesson? You can be right about everything and still lose.
Gift #4: Your People Are Your Destiny
The biggest lessons from startups #3 and #4 weren’t just about markets or timing – they were about people. In both cases, I learned the hard way that WHO you build with often matters more than WHAT you build. This isn’t just your co-founders. It’s also your investors and your board.
I don’t believe in airing dirty laundry in public. But suffice to say: stress reveals true character. When things get difficult, what people say matters less than what they actually do. When money is on the line, values become apparent – often in shocking ways.
When the storm hits, it matters a whole lot who’s in your boat. Will you pull together and row to safety or throw each other overboard?
The Gift: Who you build with matters more than what you build.
My greatest startup scars weren’t created by market failures or product mistakes – they were created by the people I surrounded myself with. Choose your partners, investors, and board members not just for what they bring when times are good, but for who they will be when everything is falling apart.
Gift #5: WHY Beats WHAT Every Time
After those brutal lessons, I thought I was done with startups. Then #5 came along and reminded me why I fell in love with entrepreneurship in the first place.
This one was different from day one. We weren’t just building a product or chasing another market opportunity – we were on a mission to stimulate innovators to solve the world’s biggest challenges through entrepreneurship.
The vision was audacious and it energized our team. But I was surprised at how much it also resonated with just about everyone we met. Investors, customers, partners, even random people at cocktail parties would light up when we explained why we existed. They didn’t just get it. They wanted to be part of the movement.
For the first time, I experienced the magnetic power of purpose-driven building. When people grasped the WHY behind what we were doing, everything became easier. Recruiting talent, raising capital, landing partnerships, even getting press coverage – doors opened because people believed in the mission, not just the product.
The Gift: When people grasp WHY you’re building, it’s infinitely more compelling than WHAT you’re building.
This experience taught me that vision isn’t just marketing speak. It’s fuel. People crave meaning in their work and want to contribute to something larger than themselves. When you can articulate a compelling “why” that goes beyond making money, you tap into something far more powerful than features, pricing, or competitive advantages. You create believers, not just customers.
Gift #6: Conviction Over Consensus
The difference between my first startup and my sixth isn’t just experience – it’s conviction. And these are two very different things that work together in powerful ways.
Conviction comes from having deep knowledge of the problem. After decades of building companies, helping thousands of others do it, and thinking deeply about how to best serve them, I’ve become a master of what’s broken in how we support entrepreneurs. This conviction tells me what needs to be built, even when it goes against accepted norms. It’s the unshakeable certainty that comes from understanding a problem so deeply that the solution becomes obvious, regardless of what conventional wisdom says.
Experience, on the other hand, is how you execute on that conviction. It’s knowing what solutions to build, how to bring them to market, which team members to hire, which investors to avoid, how to navigate board dynamics, when to pivot and when to persist. Experience is the tactical knowledge of how to build successfully – the accumulated wisdom from five startups worth of mistakes and victories.
When conviction and experience align, something powerful happens. You know not just what to build, but how to build it well (and who to build it with). You can move confidently in directions that make others uncomfortable because your conviction is grounded in deep problem knowledge, and your experience gives you the roadmap to execute.
The Gift: Conviction tells you what to build. Experience tells you how to build it. You need both.
Most entrepreneurs have one or the other – either strong conviction without execution knowledge, or solid experience but unclear vision. The magic happens when decades of problem mastery meets hard-won building wisdom. That’s when you can create something truly disruptive while avoiding the classic pitfalls that kill most startups.
Entrepreneurship Is a Long Game
I’ve built six companies, but they’re all just chapters in a longer story. Some painful, some exhilarating, all educational. Each one taught me something that prepared me (and made me more ready) for the next.
The real gift isn’t any single lesson – it’s understanding that entrepreneurship is a long game of becoming. Each version of yourself as a builder teaches the next. I am significantly wiser and entirely more confident now than the entrepreneur who started V1. That confidence didn’t come from never failing – it came from failing, learning, and building again. And again. And again.
When you focus on more than short-term exits and you view each venture as part of a larger mission, you build a legacy that transcends individual companies – one forged by decades of victories and defeats.
The question isn’t whether you’ll face setbacks or encounter forces beyond your control. You will. The question is: What version of yourself as a builder are you becoming through it all?