Dillon Ferdinandi

Category: Technology

  • 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.

  • Ten Years In

    This post was originally shared on my newsletter White Belt Mentality

    Hey friends, happy 2026!

    I hope you’re feeling healthy and well.

    It’s been a little while since I last posted, so I wanted to share a quick update and say thank you. Last year was my first full year running my coaching practice, and I’m so grateful for the people who trusted me, supported me, read along, or just reached out when something resonated.

    The majority of my work revolves around people in the middle of something. Venture-backed founders raising money or thinking about what scaling looks like after the next round. Leaders stepping up to bigger roles, managing boards, or hiring their first executive team. People selling companies, winding things down, or trying to figure out what’s next after a big chapter closes. The work isn’t about having all the answers. It’s about creating space to think clearly and move forward with confidence.

    On the personal side, Emily and I welcomed our third daughter last year. Adding another kid into the mix has been a big shift for our family – full of love, fun, and our fair share of chaos. For me, it’s also meant letting go of rigid routines and getting more comfortable adjusting on the fly.

    I also wrapped up the year with something I’ve been working towards for a long time – I received my black belt in Brazilian Jiu-Jitsu. I’ve spent over a decade on the mats and what started as a way to exercise and manage stress has transformed into a lifestyle. I spent a lot of the holiday season reflecting on the journey so far, and I thought it would be fun to share a few lessons that Jiu Jitsu has taught me.

    Consistency compounds.

    People new to Jiu Jitsu often ask how to get good fast. My answer is usually to slow down. Pick something you can sustain – maybe two or three days a week – not seven. I’ve watched more people burn out their first year than stick with it. Secondly, remember that life is always changing so allow your habits to change with it. Some seasons you train a lot. Other seasons you’re sick, exhausted, or just trying to keep your head above water. The important part is not burning out, getting hurt, or disappearing altogether.

    The real progress comes from sticking with something over a long period of time. Showing up on days when you don’t feel great, or when you feel like you’re getting worse. Going through stretches where you’re just reviewing the basics again. Then going a layer deeper. The journey is never a straight line. It’s more like a constant messy middle with occasional leaps forward that only make sense looking back.

    Get comfortable being uncomfortable.

    Jiu Jitsu puts you in tough spots constantly. You feel stuck, lost, and unsure, until you’re not and it just clicks. You’re constantly trying, failing and then trying again.

    When you’re uncomfortable in a bad position, the natural reaction is to panic – to move fast, to force something. Most of the time, that’s exactly what gets you submitted. Learning Jiu Jitsu means learning to breathe and stay calm under pressure long enough to see what’s actually happening and figure out your next move. There’s almost always another step you can take. As one of my professors always says, “it’s just action and reaction.”

    This applies to daily life and work too. We all end up in stressful, fight-or-flight situations. Our natural instincts often direct us to react quickly – to just do something! The better move is to slow down, breath, and respond or react with a clear mind. Calm doesn’t have to mean passivity. It means being able to think strategically when the situation feels intense or scary.

    You don’t do this alone.

    No one sticks with something for ten years without good people around them. Professors, training partners, and teammates make the hard days easier and the longer arc of mastery possible. Having people who notice when you’re gone (with a few guilt ridden texts!) and welcome you back matters more than most of us admit.

    Getting a black belt didn’t change much. There were no new powers or sudden insights. It just marked the start of another phase, one where the focus shifts from chasing milestones to continuing to learn. Kind of like being a white belt again and I’m finally at the real starting line.

    Thanks for being here and thanks for reading. Wherever this year is starting for you, I hope you give yourself permission to keep showing up in whatever way makes sense right now.

    Dillon

  • 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.