Dillon Ferdinandi

Tag: business

  • 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.

  • Strengthening Investor Communication

    Over the past few months, I’ve met with numerous founders preparing to raise capital in the first half of 2025. A recurring theme has surfaced: communication gaps with their existing investors.

    This trend isn’t surprising. Our industry lacks standardized communication practices between investors and founders. And given the choice, most founders would rather focus on customers, product development, and team building—the real work. However, maintaining candid investor communication is crucial—especially if you haven’t raised in a while. Neglecting it can lead to prolonged fundraising timelines, unexpected shifts in round dynamics, and challenges in securing capital when needed most.

    If this resonates with you, here are a few thoughts I’ve shared in recent conversations that might be helpful.

    1. Ship the Update

    Founders often hesitate to send updates when progress feels slow or setbacks arise. But investors prefer transparency over silence. Regular updates, even without major milestones, showcase your leadership—resilience, adaptability, and commitment to growth.

    Even if you don’t have significant product or revenue progress, share what you’re learning, experiments you’re running, and how you’re adapting. Prioritize authenticity over perfection. Your investors backed you, and regular communication fosters confidence, regardless of short-term results.

    2. Make the Update Useful — Give Homework

    Too many investor updates don’t include a request for support. These updates serve investors and their finance teams, but they should also be valuable to you. Make them mutually beneficial.

    Reflect on where you need help—introductions to new investors, potential board members, a key GTM hire, a connection to a CIO, etc. If you don’t ask, it won’t happen. If an investor isn’t responsive or their feedback isn’t helpful, that’s another issue to explore. But you won’t know unless you make the request.

    3. Ask the Awkward Questions Early

    Many founders assume their existing investors will participate in the next round, but that’s not always the case. Partners transition, fund strategies shift, and priorities change—especially in the current market. Decisions to reinvest can be impacted by many factors. A few I’ve seen recently include partner departures, fund performance, and policies around pro-rata and ownership thresholds.

    Rather than waiting until a formal fundraising process, ask the uncomfortable questions early. Push for clear answers. Doing so will save you time and energy and help you understand how to engage and leverage your investors moving forward. Ideally, investors should be engaged throughout your journey, but a direct conversation about reinvestment can surface important insights and actionable feedback early.

    Final Thoughts

    These suggestions are simply reflections from recent conversations. Building a great business is always the priority, and strong investor relationships can amplify your success.

    If you haven’t been sending updates, now is a great time to start and build the habit. Put your investors to work, and ask the tough questions now. Regular, candid communication can pave the way for smoother fundraising and stronger partnerships over the long run.