I feel like a dinosaur entrepreneur. It’s been six years but I still have the itch to start something never really goes away. Even after exiting, losing, investing, and consulting, I still catch myself sketching ideas in my notebook or breaking down market gaps while walking through a supermarket. It’s in my DNA.
But I do see the game has changed significantly. Starting a small business or launching a startup today is not what it was 10–15 years ago. Back then, I could think of 50 businesses I could bootstrap my way forward through cheap ads, affordable talent, low infrastructure costs, and plenty of white space in markets waiting to be filled. Now? It’s tough. Seeing how small startups do it, I can already see where cracks and leaks will form.
<h2>The game is harder</h2>
<strong>The costs</strong>
What used to be lean is now bloated. I remember in 2014, we could throw a few hundred dollars into Facebook or Google ads and actually get traction. Customer acquisition cost was predictable, cheap, and scalable. Today, I see our marketing cost in digital ads burn through budgets in weeks, with rising CPMs and CPCs that can be 5–10x higher than in the early 2010’s. Layer on iOS privacy changes, cookie deprecation, and attribution challenges. I wouldn’t be able to keep up this way as a startup. My marketing funnel wouldn’t just be expensive, it’s unreliable.
Talent is another hit. Skilled operators, engineers, and even mid-level staff expect a lot today. Even when I hire low skill warehouse workers, they know to ask for packages, competitive comp, and full benefits. Startups that used to thrive on sweat equity now compete with Big Tech salaries and remote-first global hiring pools.
<strong>The funding game</strong>
Funding was always an option back in 2010’s. We considered it in 2016 but the terms weren’t great compared to the way we operated. But the terms I’ve heard about today are brutal compared to a decade ago. Investors have shifted from growth-at-all-costs to demanding cleaner unit economics: lower CAC-to-LTV ratios, earlier profitability, and capital efficiency baked in from day one. I can’t sell “future potential” the same way anymore; I need traction, metrics, and a working GTM (go-to-market) engine before they’ll even take your call.
And if I were to be funded, the terms aren’t founder-friendly. Full-ratchet anti-dilution clauses, participating preferred shares, liquidation preferences that are all designed to protect the investor, not me. A founder can work themselves into the ground only to walk away with scraps if the exit doesn’t hit a certain threshold. Dilution happens faster, and the leverage is squarely in the hands of capital providers. Ten years ago, storytelling and vision could buy you more runway. Today, it’s term sheets with sharp ass teeth.
And then there’s the reality of competition. Bootstrapping used to mean you could build slowly and still find your way. Today, underfunded means you’re outspent before you can establish a foothold.
<strong>The competition</strong>
Bootstrapping was viable back in my day. Especially with my second startup, my co-founder and I had some money to really push our growth organically by adjusting our pace, reinvest cash flow, and carve out a niche. In a way we were kind of untouchable in specific category areas and key markets. Today I can’t imagine being underfunded. Big competitors today will go after every nook and crannie to out-market me. How do I know this? I’m the deep pocket competitor pushing out every small distributor from entering our space. I will out-recruit them, and simply buy time they don’t have. Me and the other larger players make survival of new players coming in basically impossible.
<h2>So what are my alternative options…</h2>
<strong>Build a smaller cashflow business</strong>
Forget chasing unicorns. In the last 5 years in different markets and businesses, I now appreciate the beauty in the boring businesses. Maybe it’s age too but solid margins can often outperform flashy startups in terms of actual quality of life. I have been randomly thinking of niche e-commerce brands like eco-friendly home goods, boutique logistics providers, or highly targeted B2B SaaS for medical practices, compliance platforms for import/export. micro-franchises, or small-scale manufacturing businesses with strong regional demand.
These don’t require venture backing, just discipline in cost management and strong GTM execution. My thinking is slow growth, less on hypergrowth and more on free cash flow and sustainability. With automation and fractional teams, I think I could run a $1–5M ARR business without raising a dime in the current entrepreneurial environment.
<strong>Buy existing business</strong>
My entrepreneur friends often talk about a growing ecosystem around search funds and SMB acquisitions that come from retiring boomer owners who built healthy but outdated businesses. So instead of starting from zero, I would be open to acquiring a business already generating $2–10M in revenue, then modernizing it with what I’m currently doing like ERP implementation, digital marketing, or streamlining SG&A with automation. The upside is I skip product-market fit risk and instead unlock growth through operational efficiency. And If I needed funding, I would structure through SBA loans, seller financing, or investor syndicates, which means I can control a valuable asset without VC money dictating terms.
<strong>Stay in the game but not as a founder</strong>
This is what I’m doing now. Being in the middle ground between the lone founder and being someone else’s employee. I think the term is fractional leadership like interim COO, CRO, or Head of Ops. I parachute into companies that need specific structure changes. Advisory gigs and board seats give you leverage on strategy without the grind of day-to-day. Go independent contracting with an intrapreneurship route: building new divisions inside larger firms that already have infrastructure, balance sheet strength, and compliance frameworks in place. You can have the thrill of building without the existential risk of funding and survival.
Truth be told they feel like consolation prizes. I get it’s the smart and safe play but personally I find it a bit limiting when it comes to my breadth of skills. Right now, I think it’s a good fit because the current market is designed to squeeze the small guy. CAC is higher, capital is stricter, compliance is heavier so my personal career strategies need to shift too. I still think about new business ideas all the time, but I can’t ignore the fact that the rules have changed. This was my way to stay in the game without being crushed by it.
<h2>What now</h2>
The funny part is, even with all this knowledge, I know it’s still not the right time yet. But that itch doesn’t go away. I’m also self-aware enough to admit something uncomfortable: My gut says it’s not the right time yet but I also know there’s never a “perfect time” and at some point, I have to pull the trigger on something. It’s not fear. I’ve never been afraid of the grind. It’s about respect for the current landscape. I can build. I can lead. But this isn’t the same market I cut my teeth in, and pretending otherwise is just self-delusion.
I have already removed those back in the day notions from my head. I’m now focused on building up a warchest, a more personalized network that’s closer to the chest, keeping a pulse on markets beyond the obvious ones or that I know. I’m writing this to hold myself accountable.