ABOUT DAN HENDERSON
Advisor. Coach. Operator.
I've spent 30 years building companies, investing in them, and leading business acquisitions as a buyer. Now I work with the founders and CEOs navigating those same decisions — as the thinking partner I wish I'd had.
The best advisors aren't the ones who tell you what to do — they're the ones who've been where you are. I've founded companies, raised capital, navigated acquisitions on both sides of the table, and led organizations through periods of growth and transition. I've made the hard calls, felt the isolation that comes with leadership, and learned what it actually takes to build something and successfully exit it. That experience is what I bring to every conversation.
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Among other ventures, I've served as a founding executive of FastSoft, a venture-backed company acquired by Akamai (NASDAQ: AKAM), and of BeClose, incubated at Alarm.com (NASDAQ: ALRM) prior to its IPO. I ran global M&A for 3Pillar Global through its acquisition by H.I.G. Capital, and spent six years as a venture investor at Virginia Venture Partners, where my portfolio companies went on to achieve valuations in the hundreds of millions of dollars.
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I hold an MBA from UCLA Anderson and an Executive Masters Certificate in Leadership Coaching from Georgetown University. I'm a Professional Certified Coach (PCC) through the International Coaching Federation — the leading global credentialing body for coaches — and hold advanced certification in executive coaching through the Center for ADHD Coaching Excellence.
EXPERIENCE
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30 years as founder, venture investor, and M&A executive​
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7 successful exits — as founder and investor
22 investments as lead investor — Virginia Venture Partners
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$300M+ combined investment value
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Head of Corporate Development — 3Pillar Global (acquired by H.I.G. Capital)
14 board positions held
CREDENTIALS
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MBA — UCLA Anderson School of Management
PCC — International Coaching Federation
Executive Masters Certificate, Leadership Coaching — Georgetown University
Advanced ADHD Coaching Certificate — CACE
30
YEARS OF EXPERIENCE
24
M&A PROJECTS LED
7
SUCCESSFUL EXITS
14
BOARD POSITIONS HELD
22
INVESTMENTS AS LEAD INVESTOR
$300M+
COMBINED INVESTMENT VALUE
ON ADHD AND LEADERSHIP
A late diagnosis that changed everything
I was diagnosed with ADHD in my mid-40s. By that point, I had built a career I was proud of — but I had also spent decades pushing through challenges I didn't fully understand, in ways I couldn't always explain. The diagnosis gave me a framework for understanding myself that I'd never had — and with it came more ease, more authenticity, and more genuine connection with the people around me.
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Many of the founders and CEOs I work with share this experience — high-achieving people who've always felt slightly out of step with the conventional playbook, who've built remarkable things partly because of how their brains work, and partly despite it. I understand that from the inside.
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What I offer isn't symptom management. It's a coaching relationship built on the understanding that our brains work differently — and that for many leaders, that difference is inseparable from what makes them effective. The goal isn't to minimize your ADHD. It's to understand it clearly enough that you can stop working against yourself and start working with how you're actually wired.
BACKGROUND
Thirty years at the table
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2022 — PRESENT
Founder — Gravity Insights LLC
Strategic advisory and executive coaching for founders and CEOs. After 30 years building and exiting companies as an entrepreneur, investor, and M&A executive, I now focus entirely on helping other leaders navigate the same terrain.
2021 — 2022
VP & Global Head of Corporate Development — 3Pillar Global
Stood up and ran the global M&A function at a private equity-backed software consultancy acquired by H.I.G. Capital. Led sourcing, diligence, and acquisitions alongside the PE sponsor. Vetted 120+ deals annually, completed 2 acquisitions in the first year.
2019 — 2021
SVP of Corporate Development — MarginEdge
Joined a high-growth, PE-backed payments company — after first leading their $2M seed round as a venture investor. Drove 10% of company revenue within 12 months at a business growing 125% YoY. Built transformational strategic partnerships with payments and accounting platforms.
2013 — 2019
Investment Director — Virginia Venture Partners
Member of the four-person investment team at an award-winning institutional seed fund backed by the Commonwealth of Virginia. Led 22 investments with a combined enterprise value of $300M+. Served as board observer at 14 portfolio companies. Notable exits: DivvyCloud (18x), Public Relay (10x), LiveSafe (7x), Rybbon/Blackhawk (4x).
2006 — 2013
Founding Executive — FastSoft, BeClose, & Others
VP of Marketing & Strategy at FastSoft, a venture-backed Internet infrastructure company spun out of Caltech — acquired by Akamai (NASDAQ: AKAM). Sourced and closed a $4.2M Series A. Founded or co-founded four companies between 2000 and 2012 across technology services, digital media, and wireless health.
OUTSIDE THE WORK
A few other things
I volunteer as a business advisor and leadership coach for Compass Pro Bono and Grounded Idealist's The Coaching Collaborative, working with nonprofits navigating growth and organizational challenges. I'm also a Patriotic Instructor with the Veterans of Foreign Wars Auxiliary, and I've served on boards and selection committees across the DC-area startup ecosystem for over a decade.
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I'm the fiddler and a vocalist in Pictrola, an award-winning professional bluegrass band that performs regularly at music festivals, concert venues, and performing arts centers. Music has always been central to who I am — the creative side, the technical side, and the kind of deep collaboration that only happens when a group of people are fully committed to something together. I've never found a better laboratory for learning how to think, listen, and work with others.