In 2011, I sent Brad Feld an email.
It was in response to something personal and vulnerable he had posted, and a message I deeply resonated with. At the time, I was a founder, a little lost, and craving connection. I didn’t expect him to reply. He’s Brad Feld, after all. But he did. Not with a quick note or a brush-off, but with a kind, heartfelt response that left me stunned.
I felt seen. I felt cared for. I felt like I mattered.
That moment stayed with me. I didn’t know it then, but I had just experienced Give First in its purest form: someone offering their time and energy with no expectation of return. Just to help. Just to connect.
Years later, in 2017, I found myself as a CTO founder going through the Techstars Boulder program. That’s when Give First became more than a memory; it became a practice. It gave a name to something I had already been doing for years through my volunteer work with Go Code Colorado, mentoring startup teams and coaching other technology leaders, often without even realizing that I was operating from this same principle.
Give First means being willing to help someone without the expectation of getting something back. It’s not altruism. It’s not transactional. It’s trust.
Becoming a Giver (Even When I Had Little to Give)
My path to becoming a mentor was non-linear. Early in my career, I had the good fortune of being surrounded by technology leaders who saw potential in me. Their belief encouraged me to reach higher. But over time, the landscape changed. I found myself in rooms filled with transactional leaders—those who wielded power at the expense of others. The kind of people whose leadership became examples of what not to be.
I’ve had more of those experiences than I care to count. And strangely, they make me a better mentor. They remind me what it feels like to walk into uncertainty and find no one there to guide you. They gave me the fuel to become the kind of supporter I wish I had during the hardest parts of my own journey.
When I launched my first company in 2007, a software consultancy, I had to step out of my comfort zone in every way. I’m a deep introvert by nature, but I had to force myself to show up if I was going to sell our services and deliver successful outcomes for our clients. I knew I needed to get comfortable with this, so I volunteered. I mentored. I engaged. Over and over again to build this skill. And in doing so, I discovered my own self more fully.
What Giving Has Given Me
People often think of mentoring as a gift you give to others. But let me be clear: I am the one who’s benefited most.
Giving first has sharpened my thinking. It’s exposed me to challenges I might never have encountered on my own. It’s helped me codify what I know—eventually becoming the foundation of the CTO Levels framework and my forthcoming book, Liquid. And it’s made me unafraid. There’s almost no situation that rattles me anymore. I’ve seen it all. And I’ve seen it because I keep showing up to help others solve their hardest problems.
But the greatest reward by far is the trust. When a mentee opens up to you, lets you into their uncertainty, and invites you to walk beside them for a while—that’s sacred. That kind of trust fills me up in a way no business success ever could.
Letting Go of the Return
The most powerful shift in my understanding of Give First came when I finally internalized the idea of expecting nothing in return.
Brad writes about this beautifully in the Give First book. It sounds simple, but it’s not. We all want to believe we’re being generous. But if we’re secretly tallying outcomes or waiting for recognition, we’ve turned generosity into a transaction.
Letting go of expectations doesn’t mean you won’t receive anything. Quite the opposite. The returns will come. Just not in the form, time, or direction you expect. When I stopped needing a specific outcome from each act of giving, I started noticing the astonishing, unpredictable ways the universe shows up to return the favor.
I’ve learned to trust the rhythm of reciprocity. I give what I can, to the people and causes where I know I can make a difference. And I trust that what comes back will be reshaped by time, guided by purpose, and aligned with needs I hadn’t even discovered yet.
Full Circle
Giving first isn’t something I plan anymore; it’s become a natural rhythm for how I show up. Since 2017, I’ve mentored at least one Techstars company every year (often more). I’ve made it a personal mission to bring more CTOs into the mentorship pool, so future founders have access to support I didn’t have in my program. I speak regularly at conferences to CTOs and CEOs alike. I consistently play matchmaker between CEOs and CTOs to help their businesses thrive. I coach and advise CTOs so they don’t have to make it all up as they go.
I will never forget the moment after I spoke at Techstars FounderCon in 2023 when a couple came up to me after my talk, both in tears, telling me that my talk saved their marriage, because it gave them a language to be both CEO/CTO together AND partners in life. Then moments later Techstars surprised me with their #GiveFirst award.
This is what it means to Give First. The absolute, unexpected gifts this synchronicity manifests down the line when we least expect it. And I learned it from the people who opened my eyes to what is possible. Brad and Techstars among them.
A Thank You, and an Invitation
Brad has given so much to the startup ecosystem through Techstars, his work as a VC, through his blog, through his writing, and through his presence. His new book, Give First, is not just a chronicle of that work. It’s a blueprint for how to build a world where generosity, authenticity, and trust lead the way.
If you’re someone who’s been walking the line between generosity and self-protection, or if you’ve felt burned by giving too much to the wrong people—this book is for you.
If you’re someone who wants to give more but doesn’t know how to start—this book is for you too.
And if you’re already living this way—thank you. You’re part of what’s keeping this ecosystem human.
So please—buy the book. Read it. Reflect on it. Share it.
And then find one way, this week, to Give First. You won’t regret it. I never have.