Dillon Ferdinandi

Tag: life

  • Joining Opacity

    Getting back into the arena

    At the end of 2025, I started feeling the pull to get back into a startup. I still love the work I do with my coaching and advisory clients, and I plan to keep doing it, but I’m a team player at heart. I missed being in the arena with a small group of people working toward the same goal. Even venture investing, which I enjoyed for a long time, felt surprisingly solitary.

    After some reflection, I made a short list of what I wanted next: a great founder(s), an exciting problem to solve, the ability to work in person, and a role that would stretch me.

    I didn’t expect to find the right thing this fast but sometimes the timing works out in ways you can’t really plan. This week, I’m joining the founding team at Opacity.

    Great founder

    One of the things I’ve learned over the years is that the founder matters more than almost anything else.

    A family member had been trying to introduce me to Drew Wilson for years. The timing never quite lined up. Then, the very week Drew left Clerk to start Opacity, we finally connected. I think the timing was meant to be.

    We met for coffee a bunch of times and talked about technology, investing, design, and company building. All the conversations that are easy to have when you’re genuinely curious about the same things.

    When I told him I was thinking about getting back into a startup, he asked if I wanted to join. I didn’t need long to think about it. Drew’s a serial founder, and he’s already pulled together a strong group of designers and developers. It felt like the kind of team I wanted to be part of again.

    Interesting problem

    For most of my career, I have  lived at the intersection of design, product, engineering, and the people who actually use the things we build. Over that time, I’ve watched a few major shifts in how software gets made. At Slack Fund, I spent years finding and investing in “future-of-work” tools that made it easier for more people to create software.

    Through all of that, one tension never really went away. Designers created in one world, engineers built in another, and the gap between those two worlds never fully closed.

    It’s pretty incredible how much AI has accelerated software development. People who couldn’t write code a few years ago can now build real products, and experienced engineers are more productive than ever. With that said, we still don’t have anything close to that shift for designers. And almost nobody is building for what happens after the prototype – the messy part where real software gets shipped, teams collaborate, and the product becomes the source of truth for the company.

    That’s the space Opacity is working in, and it’s a problem I’m excited to help solve for builders.

    Working in person

    When we left San Francisco for Carlsbad more than five years ago, it was exactly the change our family needed. We had twins, I had finished cancer treatment, and we were in the middle of the COVID pandemic. Remote work perfectly fit the season of life we were in.

    We’ve built an incredible community in San Diego, and I wouldn’t trade this chapter for anything. But over the last year I started to realize how much I missed the energy of being in the same room as the people I work with.

    There’s a kind of momentum that only shows up when you’re building something together in person. Conversations happen faster, ideas get sharper, and relationships go deeper. Opacity isn’t fully in San Diego, and we’re not fully in person, but Drew is here in Carlsbad, and we’re building around a local network as the team grows. That matters more to me than I would have expected a few years ago.

    A fun role

    When I look back on my career, the word that comes to mind is generalist. 

    I’ve moved between product, investing, partnerships, operations, and coaching. Not because I had some master plan, but because I kept following the things that felt interesting or important at the time. The result is a mix of experiences that don’t fit neatly into one title, but have taught me how companies actually work.

    I wanted to find something where I could use all of that.

    The best analogy I have is from sports. Some people run a marathon once and decide they never need to do it again. Others finish and immediately start thinking about how they could do it better the next time.

    Right now I feel like the second kind.

    I’ve learned a lot over the past decade. I’ve worked with people who are far better than me at specific things, and I’ve been lucky enough to see how great companies get built from the inside. This felt like the right moment to step back into that environment and see what I can do with everything I’ve learned.

    At this stage, titles don’t matter much. Early teams are all utility players. My job is to do whatever helps us get a great product into customers’ hands, make sure it actually solves a real problem, and help build the team and operating foundation we’ll need as we grow.

    It’s still very early, and while there is plenty of uncertainty ahead, it feels like exactly the right moment to be back in the arena.

    If you want to follow along, we’re building at opacity.com.

    I’m still coaching! Through this I am continuing to work with a small group of founders through my practice Grandview Performance Coaching. That work isn’t going anywhere. If anything, being back inside a startup makes me more fired up to support founders.

  • The Long Game

    January is just one month. Don’t burn out trying to prove to everyone and yourself that you’ve changed.

    This post was originally shared on my newsletter the White Belt Mentality

    Every January, the same motivational messages start taking over our socials and inboxes – “New Year, New You! This is the year everything changes!” “Time to lock in!!” Energy is high and people want to share that momentum (or sell you something that does).

    That’s great for them, but that’s not where many of us find ourselves sitting with the new year. Often times it feels like the same exhaustion and stress but with a calendar reset.

    We’re coming off the holiday season, which is usually less of a time to ‘rest and recharge’ and in reality is filled with travel, illness, complicated family dynamics, kids home from school, and the frantic push to close out the year.

    If you’re a founder or a leader you also have the added weight of unfinished goals, big decisions looming, or just the anxiety of “what’s next?” When you’re sitting in that place the constant “Let’s go! Crush it!” often doesn’t feel motivating.

    When my twins were young, I had long stretches where I was barely treading water. I was showing up, but I was a shell of myself, constantly on the edge of falling apart from lack of sleep and relentless demand. Later, after I was diagnosed with cancer, just getting through the day was a win. My body and mind definitely we’re “leveling up”. They were rapidly declining.

    We all have our own version of this, but the collective new year messaging of January rarely leaves room for it.

    Not every season is for acceleration

    Real life rarely moves up and to the right consistently. There are definitely seasons for building and riding the wave of momentum. But we also need to leave space for seasons of maintenance, recovery, struggle, or simply letting go. None of them are failures and not setting big audacious goals doesn’t mean there’s something wrong.

    In my coaching work, I talk to founders and leaders who are navigating the end of relationships, quietly winding down a business, carrying a diagnosis they haven’t shared, or just feel deeply burned out (or unmotivated). These are some of the most capable and ambitious people I’ve ever met. And they aren’t behind. They’re just in a different chapter or season of life.

    When “I’m not crushing it” is the truth

    One of the most common things I hear this time of year is some version of: “I know I should feel excited… but I don’t.” If that’s you: that doesn’t mean something is wrong with you. It means you’re paying attention.

    Sometimes the most honest (and the bravest) thing you can say is:

    • I don’t have big goals right now.
    • I don’t know what’s next.
    • I need to stabilize things before I can grow.
    • I’m just tired.

    During these seasons progress looks like showing up. Doing the small things. Just not quitting. Keeping the lights on. Or maybe asking for help. Sometimes the right goal is just consistency.

    The only scorecard that matters

    This is the core ethos of the The White Belt Mentality. You are on your own journey. The only comparison that actually matters is who you are today versus who you were yesterday. And putting in the daily work toward where you want to go.

    Progress isn’t measured against someone else’s highlight reel or their January enthusiasm. It’s measured internally, over time, and with the appropriate context.

    A white belt doesn’t worry about where they’ll be in five years. They worry about their stance. They show up, they learn, and they survive the next round. But they come back tomorrow.

    That’s enough.

    “But… life is really good right now!”

    If that’s you, that’s incredible! Seriously. Enjoy it.

    If you have the momentum, ride it, and see where it will take you. But do it with humility. Momentum is a gift. Most of us won’t feel high energy forever. So soak it in, be grateful, and maybe reach out to a friend who isn’t having the same kind of January. They might need that connection more than they’ll say.

    A permission slip (and small invitation)

    If this year is starting slow for you that doesn’t mean it will end small.

    You don’t owe the New Year a reinvention. You don’t owe January a breakthrough. You don’t owe anyone proof that you’re “on.”

    Some seasons are all about growth. Some are about holding steady. Some are about healing. All of them count. If this is a quiet, heavy, or just an uncertain start for you, know you’re not alone. And you’re definitely not doing it wrong.

    Just keep showing up. That’s the real work.