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3 Things I Wish I Knew When Founding a Company 20 Years Ago
3 Things I Wish I Knew When Founding a Company 20 Years Ago

Entrepreneur

time35 minutes ago

  • Business
  • Entrepreneur

3 Things I Wish I Knew When Founding a Company 20 Years Ago

If I could sit down with a new B2B founder today, these are the three conversations I'd make sure we had — the same ones I wish someone had with me early on. Opinions expressed by Entrepreneur contributors are their own. Twenty years ago, I launched my company with a head full of optimism and a thin playbook. The market was smaller, capital was scarcer, and the word "scale" usually referred to manufacturing, not software. Let me save you twenty years. Through three recessions, a pandemic and a Russian hack I'll never forget, I learned that every outcome — good and bad — was dictated by three things: approach to equity, obsession with speed and commitment to building for the future, not just the present. If I could sit down with a new B2B founder today, these are the three conversations I'd make sure we had — the same ones I wish someone had with me early on. Join top CEOs, founders and operators at the Level Up conference to unlock strategies for scaling your business, boosting revenue and building sustainable success. 1. Don't give it all away Early on, most founders pay their first hires in equity. Each grant solves an immediate payroll problem but also sets the "going rate" for everyone who follows and nibbles away at the founder's ownership. Over time, as more hires come on board expecting similar equity deals, the option pool expands, and suddenly, there's not enough left to offer meaningful stakes to the senior leaders who matter most for the company's next phase of growth. To fix this imbalance, you must recognize that you have precisely one window to fix it, and that's now. It means having the hard conversations about revisiting vesting, adding performance cliffs and making room for future partners. The pain of doing it now is nothing compared to the pain of explaining a broken cap table to new investors. We survived a similar case because we ripped that band-aid off, just before our next round made it impossible to do so. Today, I tell founders to treat equity like a reserved seat at the board table: only give it to people whose judgment you'll still respect a decade later. If only I had known that timing and value alignment in equity partnerships mattered so much, I would have saved myself countless hours of renegotiation had it been available back then. Related: 3 Things to Consider Before Going 'All in' on Your Startup 2. Move faster than feels comfortable Another blind spot for most founders is velocity, which goes unnoticed until it starts costing real money. Founders who insist on flawless forecasts and endless debate often end up watching the market sprint ahead while their projects idle in "analysis" mode. It's crucial to remember that most opportunities have a shelf life, and the price of hesitation usually outweighs the cost of a measured mistake. With that in mind, I had to make sure our teams embrace a bias toward action. Each year, we challenge ourselves to shorten our decision-to-execution cycle. We concentrate on the highest-payoff priorities, make the call, and then move immediately. While we may inevitably miss the mark at times, we correct them faster than we once made them. Clearly, there's no substitute for experience. The older I get, and the more seasoned our leadership team becomes, the quicker we can weigh risks, spot patterns and avoid analysis paralysis. That pace creates its own momentum. Once speed becomes the expected culture, your team instinctively builds processes to protect it. So when early-stage founders ask me how fast they should move, my answer is always faster than you think, and then faster still. Related: What Every B2B Brand Should Be Doing to Earn Trust in 2025 3. Build like you're already big In hindsight, we made the classic mistake of building to match the previous quarter's demand instead of our initial goals. We told ourselves that fifty customers was a stretch, so we provisioned servers, support seats and deployment scripts for a company that size — nothing more. As we started to scale, sales momentum started inching us closer and closer towards the ambitious 5,000-site mark we'd only daydreamed about. Many founders discover, right in the middle of a launch, that an early single-tenant setup and bare-bones deployment pipeline won't stretch to meet sudden demand. Deadlines start to drift while the team upgrades to multi-tenant architecture and spins up redundant cloud instances. The extra spend always outruns what a forward-looking investment would have cost, yet the experience makes scaling cheaper while it's still in theory. That's why every roadmap review should open with a simple stress test. For example, for us, "What breaks if we need to bring 150 sites online next month?" — and why budgets must include the infrastructure to pass that test, even when today's revenue makes the line item look ambitious. Planning for surge capacity before it's urgent keeps launches on schedule and turns growth into a feature, not a fire drill. The second truth is that infrastructure alone won't save you; the people building and running it will. Think of your core team as the "founding fathers" of a forever company. You need complementary skill sets, shared loyalty and relationships that hold under pressure because pressure will definitely come. Get that inner circle right, and you'll have the resilience (and the conviction) to keep investing ahead of your growth curve. The uncomfortable math of first principles Looking back across twenty years, I see with perfect clarity how every triumph and setback connects to our first principles. Mind you that those choices were never comfortable in real time as they tug on payroll, patience and budgets that already feel stretched. But that discipline consistently bought us agility. It gave us the freedom to pivot when the market turned and the readiness to jump on a once-in-a-decade chance. That, more than any clever tactic, is how you build an institution designed to outlast its founding story.

'Celebrated jeweller' Sir Michael Hill dies aged 86
'Celebrated jeweller' Sir Michael Hill dies aged 86

ABC News

time2 days ago

  • Business
  • ABC News

'Celebrated jeweller' Sir Michael Hill dies aged 86

Sir Michael Hill, the founder of jewellery brand Michael Hill, has died aged 86. The company announced "with great sadness" the passing of their founder in a statement released on Tuesday. "The Board, Executive and all the Michael Hill team express their deepest and sincerest condolences to Michael's family and friends." The company has remembered Sir Michael as a "celebrated jeweller, entrepreneur, philanthropist and committed father and husband".

Jewellery entrepreneur Sir Michael Hill dies
Jewellery entrepreneur Sir Michael Hill dies

RNZ News

time2 days ago

  • Business
  • RNZ News

Jewellery entrepreneur Sir Michael Hill dies

Sir Michael Hill. Photo: supplied Sir Michael Hill has died. The founder of the well-known chain of jewellery stores was 86. Sir Michael died on Tuesday morning, according to a statement from the business he founded to the New Zealand and Australian stock exchanges. Born in Whangarei, Sir Michael worked as a young man for his uncle, Arthur Fisher, at the family jewellery store. In 1979 he opened his own store nearby, and over the next 45 years the chain expanded to nearly 300 (281 in April 2023) stores in Australia and Canada as well as New Zealand. The company, now based in Brisbane, is currently chaired by Rob Fyfe. In 2001 Sir Michael's lifelong love of violin music led him to found the biennial Michael Hill International Violin Competition for 'emerging young violinists'. He was knighted in 2011. More to come...

Why leaders who collaborate and form communities grow faster
Why leaders who collaborate and form communities grow faster

Fast Company

time2 days ago

  • Business
  • Fast Company

Why leaders who collaborate and form communities grow faster

I used to believe that growth was a solo sprint. If I worked hard enough, fast enough, and long enough, I'd get there. However, what I've learned as a speaker, writer, and entrepreneur is that growth is actually shaped and strengthened by the people you work alongside. We often talk about scaling through capital or technology, but sometimes the most powerful accelerator is connection. When I started actively seeking out peer networks—rooms filled with smart, driven people outside my own lane—my strategy changed. My ideas got sharper. My knowledge gaps became visible. My work, especially as a storyteller, felt less like shouting into the void and more like a conversation with people who saw things I didn't. In this article, I'll share what I've learned about peer networks and why every founder, creator, or changemaker should build one with intention. When you're surrounded by people who approach problems from completely different angles, it forces you to reconsider your assumptions and sharpen your ideas. Some of my most significant turning points came from small moments, like a friend in retail helping me rethink user onboarding or a healthcare founder offering a new take on accessibility in digital content. That's the value of range. It doesn't matter if someone is in logistics or live entertainment; when they think differently, they help you do better work. Research backs this up. An MIT study introduced the concept of x-teams, which are agile groups that regularly engage with people who don't share their core function. By engaging with peers outside their domain, these teams became more innovative and adaptable. This drives creativity and outcomes that are more practical and ready for implementation. COLLABORATION BREEDS ACCOUNTABILITY Ideas are one thing; action is another. The biggest hurdle I've seen, especially for solo founders or consultants, isn't a lack of ideas. It's a lack of follow-through. That's why peer accountability can be a powerful motivator. When you share your goals with a group of driven people, you don't just make promises to yourself. You make them to a room full of people watching, cheering, and pushing you to move. Having an accountability partner comes with powerful psychological benefits. It helps individuals stay consistent, motivated, and committed to their goals. This mutual support system creates a sense of responsibility not just to oneself but to someone else, increasing the likelihood of follow-through even during challenging periods. I've seen this play out in mastermind groups where someone will say, 'Did you ever launch that landing page?' or 'You said you were going to pitch that publication. Did you?' These aren't just nudges; they're catalysts. When your peers believe in your potential, it gets harder to hide from it. FEEDBACK LOOPS DRIVE INNOVATION We love to glorify the gut instinct, but even the sharpest instinct benefits from feedback. One of the most overlooked parts of peer networks is the role they play in real-time iteration. I've tested pitches, headlines, and even business models in small rooms before putting them out publicly. Each time, I walked away with sharper, more innovative work. That's because feedback in a safe, intelligent environment helps you fail faster and grow quicker. According to Harvard Business Review, consistent feedback is strongly linked to higher job satisfaction. Constructive feedback, in particular, plays a crucial role by offering clear direction for growth and helping identify areas for improvement. The same principle applies to peer communities, mastermind groups, or even casual founder circles. The best ideas are rarely born in isolation. They're pressure-tested by people who ask, 'Have you thought about it this way?' or 'What if you did less, but better?' Those are the questions that move a good strategy toward greatness. COLLABORATION OUTLIVES THE PROGRAM Some of the most valuable connections I've made didn't come from networking events. They came from programs where people built something together. That's why structured peer groups, like accelerators or leadership collectives, are so powerful. I recently met with Dr. Carmen Bell-Ross, a leadership strategist and founder of SP Grace. When she joined the Goldman Sachs 10,000 Small Businesses program, her goal was to strengthen her company's growth strategy. What she left with was far more than a new business plan. In working alongside 29 other founders from vastly different industries, she found a network that became a sounding board, a challenge circle, and, in many ways, a co-pilot team. Their feedback helped her refine her service offering, The College Smarter Method, before launch. It wasn't just the curriculum that shaped her next move. It was the people. She's not alone. A Babson College impact study on the Goldman Sachs program found that 66% of alumni increased revenues within six months of completing the program, and 46% created new jobs. This tells us something important. Business success doesn't live in a vacuum. It's shaped in a community. A FINAL THOUGHT: BUILD YOUR TABLE If there's one lesson I keep returning to, it's this: Build your table before you need it. The peer network that accelerates your next move won't materialize overnight. It takes intentionality—one conversation, one collaboration, and one shared Google Doc at a time. Reach out to people in different sectors. Offer value before you ask for it. Show up consistently, and when you find your people—the ones who challenge you, support you, and help you refine your thinking—invest in those relationships. While tools and tactics change, the human connections that drive business remain.

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