“Winning” sounds simple until you try to define it without drifting into clichés or chest thumping. In our world, where we spend our days starting, acquiring, and building businesses with capital, time, talent, and technology, the idea deserves sharper edges. We are not playing a game that ends at the final buzzer. We are building systems that keep paying out in health, energy, and results.
We help leaders do the most important work of their careers, and we try to make that work feel like something you would brag about to your future self. We do all of this with patience, curiosity, and a steady willingness to be boring in the short term so we can be interesting in the long term. That is the mindset that guides our holding company, and it is the frame for our definition of “winning.”
Winning is functional. It looks like decisions that age well, teams that become more capable every quarter, and customers who can describe our value without using buzzwords. If an outsider cannot tell what we do and why it matters, we are not winning yet. Clarity is step one. Step two is compounding. Step three is doing the first two steps again, only cleaner and faster.
Winning is also emotional. It feels like walking into a Monday with calm focus rather than panic. It feels like the kind of confidence you get from a reliable engine, not a lottery ticket. It sounds like honest debates, short meetings with real outcomes, and a lot of laughter left in the hall after the lights go off. It smells like coffee at 6 a.m. and clean code at noon. It ends with products that earn trust, not attention alone.
Money is a lagging indicator of decisions made months earlier. We want durable cash generation, efficient balance sheets, and return on invested capital that beats our hurdle without drama. Growth is welcome, yet only if it pays its own way within a reasonable time.
We like profits that repeat, not one-hit wonders. Our scoreboard celebrates boring wins: lower churn, faster payback, and pricing that honors value created. Revenue that sticks is better than revenue that shouts.
We hire for builders who think like owners. Winning shows up in a culture where feedback is a gift, accountability is normal, and kindness is the default. Titles matter less than outcomes. Meetings are short, preparation is long, and documentation is explicit.
We want teammates who can disagree without becoming disagreeable, who listen for the second answer, and who can explain a complex topic in plain language. If new hires become better versions of themselves in a year, we are winning.
Users do not care about our strategy decks. They care about whether the product is coherent, fast, and trustworthy. We win when customers depend on us quietly, renew without haggling, and send us their friends without being asked. Craft matters. Details are not decoration. Good onboarding, sensible defaults, and support that solves problems on the first touch are not nice-to-haves. They are the work.
When we start something new, we begin with a brutally small problem and a narrow audience. We interview real people, write the painful truths on paper, and ship the minimum useful version. We watch what users do, not what they say. We add features only after the core loop is proven. We write the operating memo before the brand narrative so we do not fall in love with our own adjectives. The goal is traction that survives contact with reality.
When we acquire, we look for stable cores with room to breathe. We value clean books, steady customers, and teams that already care. We say no when the deal only makes sense in a spreadsheet. Post-close, we prioritize trust, not fireworks. Day one is for listening. Day two is for simplification. Day three is for focus. We remove busywork, modernize the essentials, and create a simple plan that the operating team can actually finish before the next quarter ends.
Building is a craft and a calendar. We set annual intentions in pencil and quarterly plans in pen. We publish scorecards that a new hire can read in five minutes. We automate the obvious, standardize the repetitive, and reserve human talent for the creative and the gnarly. We pair engineers with operators so product decisions consider both elegance and margin. We prune as often as we plant because resources are finite and attention is precious.
Winning likes discipline. We keep our promises to ourselves. We maintain checklists because our brains have better uses than remembering steps thirteen through seventeen. We close the books on time. We document decisions so no one has to read minds. We practice incident reviews that search for causes, not culprits. We track the cost of complexity like it is a line item, because it is.
We also invest in energy. Burnout is expensive. We treat rest like a performance enhancer. We design workflows that protect deep work. We keep meetings off the calendar unless a meeting is the only way to get the job done. We choose clarity over cleverness in our communications. And yes, we still like a good joke in the standup because a room that laughs together learns faster.
A company can drown in opportunities. We filter with three tests. First, is the problem painful enough that customers will pay and stay. Second, do we have a structural edge that compounds, like a data advantage or a distribution channel that gets stronger as we grow. Third, will working on this make our team more capable. If any answer is no, we pass with gratitude. Saying no is not a failure. It is maintenance of the engine.
We treat risk like weather. You cannot stop the rain, but you can pick a good roof. We diversify revenue where it makes sense, keep enough dry powder, and avoid key person traps. We prefer reversible decisions when uncertainty is high and commit slowly until the map is clearer. We hedge on inputs we cannot control and rehearse the unthinkable so it is less scary when it knocks. Resilience is not bravado. It is preparation plus calm execution.
Technology is a lever, not a shrine. We adopt tools that reduce toil, shrink cycle times, and improve accuracy. We build when it gives us an advantage and buy when it does not. We prefer open standards, clear interfaces, and platforms that play nicely with others.
We chase performance and security because speed without trust is a party trick, and trust without speed is a museum piece. We monitor with dashboards that show the truth rather than the story we hope to see.
Leaders set tempo and remove friction. They trade control for clarity and build teams that can act without asking for permission every hour. They coach in public, praise specifically, and own their mistakes out loud. They ask simple questions, like what problem did we solve for the customer today, and what did we learn that changes our plan tomorrow. They carry the weight when things break and share the wins when things work.
We plan in seasons. In the next ninety days, we aim for tight execution and fast learning. In the next year, we aim for crisp profitability and steady growth. In the next decade, we aim for a portfolio of engines that hum on their own, supported by leaders who started as rookies and stayed to become mentors. Victory is not a single trophy. It is a shelf that fills slowly with work we are proud to sign.
This definition keeps us honest. It refuses fuzzy metrics, glittering generalities, and goals that depend on someone else blinking first. It asks us to be humble about what we do not know, serious about what we promise, and joyful about the craft of building. It gives us permission to pick the unsexy fix if it speeds the whole system. It urges us to protect energy, not just hours. It reminds us that profit is the price of freedom and trust is the currency of progress.
Winning is a daily practice, not a dramatic moment. It is the steady reward for clarity, craft, and compounding effort. Our approach favors momentum over theatrics, kindness over noise, and resilience over hype. If we do the ordinary things extraordinarily well, if we honor customers and grow people, the scoreboard tends to smile back. That is the kind of victory we are here for, and it is the only kind that lasts.
Ryan Schwab serves as Chief Revenue Officer at HOLD.co, where he leads all revenue generation, business development, and growth strategy efforts. With a proven track record in scaling technology, media, and services businesses, Ryan focuses on driving top-line performance across HOLD.co’s portfolio through disciplined sales systems, strategic partnerships, and AI-driven marketing automation. Prior to joining HOLD.co, Ryan held senior leadership roles in high-growth companies, where he built and led revenue teams, developed go-to-market strategies, and spearheaded digital transformation initiatives. His approach blends data-driven decision-making with deep market insight to fuel sustainable, scalable growth.
