"Oh Sure, We'll Figure It Out": What Dick Beedon Taught Me About Building

Photo Taken at Unison’s Board Meeting, October 20th, 2017

I still catch myself wanting to text Dick about a problem I'm working through. It's been years since he passed in 2018, but I still have that impulse to run an idea by him, to get his take on a tricky situation, it never really goes away when someone shapes you that fundamentally.

I met Dick in the summer of 2012, right as I was diving headfirst into my first startup. I was twenty years old, thought I knew everything, and definitely didn't know anything. Dick had this way about him. Encouraging, optimistic, but with an almost surgical ability to deliver feedback that didn't make you defensive. He'd package hard truths in a way that made you want to lean in rather than shut down. I don't know how he did it. I've tried to replicate it with younger founders I work with now, and I'm not sure I've ever quite nailed his approach.

What struck me immediately was that Dick was an entrepreneur's entrepreneur. He didn't just build businesses. He genuinely loved the process. Loved kicking around ideas at breakfast, loved poking holes in assumptions, loved the refinement process of taking something rough and making it sharp. I'd watch him light up talking about go-to-market strategies for enterprise software companies, and you could tell this wasn't work for him. This was what he was built to do.

The Unison Reality Check

The most important business lesson Dick ever taught me came during a brutally honest conversation about Unison. We'd been growing, getting traction, and I was feeling pretty good about our progress. Dick sat me down and said something like, "You know what your real problem is? People see you as a services business. And until you solve that perception problem, you're never going to scale the way you want to."

I remember being frustrated at first. We weren't just a services business. We had product, we had vision. But Dick wasn't done.

"I'm not saying you ARE a services business," he continued, in that patient Midwestern way of his. "I'm saying that's what people see. And in enterprise software, perception dictates what kind of capital you can raise, what kind of talent you can attract, what kind of valuations you can command. You need to fix the packaging."

He was completely right. That conversation changed our entire trajectory. We repositioned everything. How we talked about ourselves, how we structured deals, how we presented our roadmap. It was uncomfortable work, but necessary work. Dick had a gift for identifying the one fundamental issue that, if left unaddressed, would cap your potential. And he'd push you to face it head-on.

Beyond the Code

Dick pushed me in ways that went far beyond business strategy. Here I was, a software developer who loved staying in my lane. Writing code, solving technical problems, avoiding people when possible. Dick saw something different. Or maybe he just refused to let me hide.

"You need to get out there," he'd tell me. "Learn the business side. You can code all day long, but if you can't sell, if you can't understand what makes a business actually work, you're limiting yourself."

More than that, he pushed me on relationships. Not networking in that shallow, transactional way everyone hates, but actually getting to know people. Understanding what motivates them, what scares them, what they're trying to build.

"Ask better questions," he'd say. "Stop networking and start actually caring about people. You'll be shocked how much more you learn."

I resisted this at first. I was an introvert. I was technical. Wasn't that enough? But Dick wouldn't let me off the hook. He'd drag me to events, introduce me to people, and then debrief with me afterward about what I'd learned. He turned relationship-building into a skill I could develop, rather than some innate trait I either had or didn't have.

Looking back, this might have been the most transformative thing Dick did for me. He took a twenty-year-old kid who just wanted to write code and pushed me to become someone who could actually build and lead a business. He saw potential I didn't see in myself.

"Oh Sure, We'll Figure It Out"

What I miss most about Dick is his attitude. That unshakeable, deeply Midwestern optimism that wasn't naive. It was just grounded in experience. He'd seen enough problems get solved, enough businesses pivot successfully, enough entrepreneurs overcome seemingly impossible odds, that his default setting was: "Oh sure, we'll figure it out."

I remember calling him once when we'd lost a major deal I thought we'd had locked up. I was spiraling, catastrophizing about what it meant for the business. Dick listened for about thirty seconds and then said, "Okay, so that happened. What are we doing tomorrow?"

No platitudes about how everything happens for a reason. No false reassurance that it wasn't a big deal. Just: what's next? Let's get it done. Move forward.

He'd faced his own significant health challenges over the years, and even then, even when I knew he was dealing with serious issues, he'd still show up. Sometimes physically in the boardroom. Sometimes via text at odd hours with a thought about something we'd discussed weeks earlier. His generosity with his time never wavered, even when time itself became precious.

The Giving Back Gene

Dick had this almost compulsive need to give back to entrepreneurs. It wasn't performative. He genuinely got energy from helping people build things. I'd see him at events, cornered by some twenty-two-year-old with a half-baked idea, and he'd give that person the same quality attention he'd give to a seasoned CEO. He took everyone seriously.

He used to say something like, "Someone helped me when I was getting started. I'm just returning the favor." But it was more than obligation. He loved it. Loved seeing the light bulb go on when someone grasped a new concept. Loved watching entrepreneurs he'd advised succeed. Loved the entire ecosystem of people building and creating and trying.

One of his favorite things to do was introduce people to each other. He'd sit back with this satisfied smile while two people he'd connected started riffing on potential partnerships or collaborations. "That's how things get built," he'd say. "Good people finding each other."

I think about that now when younger founders reach out to me. Dick modeled what it looks like to be genuinely generous with your time and knowledge, not because you're keeping score, but because that's just what you do. You help the next generation because someone helped you.

Resilience as a Practice

Dick talked about resilience a lot, but not in that abstract, motivational poster kind of way. He talked about it as a muscle you develop. A practice you commit to.

"You're going to get knocked down," he told me early on. "That's not the question. The question is: how quickly can you get back up? And what do you learn while you're down there?"

He modeled this constantly. When things went wrong, and in business things always go wrong, he'd take a beat, process it, and then immediately shift into problem-solving mode. No wallowing. No extended pity parties. Just: okay, here's where we are, here's what we need to do differently.

This was especially important for me at twenty. I didn't have the experience to know that setbacks were normal. That losing a deal or making a hiring mistake or pivoting your strategy wasn't the end of the world. Dick gave me permission to fail, but also showed me how to fail forward. How to extract the lesson and keep moving.

I try to channel that now when things get hard. I ask myself: what would Dick say? And the answer is usually some version of "Oh sure, we'll figure it out. Let's get to work."

Someone You Can’t Replace

When Dick passed in 2018, I lost not just a mentor and friend, but someone who was effectively family. The kind of person whose opinion mattered more than almost anyone else's. The kind of person whose approval you sought not because you needed it, but because you respected him so deeply that it actually meant something.

I still find myself in situations where I desperately wish I could get his take. A thorny business problem. A decision about whether to pursue an opportunity. How to deliver difficult feedback to someone in a way they can actually hear it. Dick had this wisdom that came from building multiple companies, from failing and succeeding, from just being in the arena for decades.

We lost him far too early. He had so much more to give, so many more entrepreneurs to help, so many more businesses to build or advise or improve. But I'm grateful, deeply grateful, for the time I did get with him. For every conversation, every piece of advice, every "oh sure, we'll figure it out" when I was convinced we wouldn't.

Dick taught me how to evaluate businesses with a critical but constructive eye. He taught me that your network is only as valuable as the depth of your relationships. He taught me that resilience isn't about never falling down. It's about getting back up, learning, and moving forward.

Mostly, though, he taught me what it looks like to be generous with your knowledge, your time, and your optimism. To believe in people before they believe in themselves. To give back not because you have to, but because you can't imagine doing anything else.

I miss him every day. And I'm trying my best to pass forward what he gave to me.

True inspiration. Incredibly kind human. And someone we lost far too early.