I Cracked the Code to Building Massively Successful Startups (With My $500M Friend)

And figured out why most of us entrepreneurs never will.

Building a company isn’t a great feat. To be honest, most anyone with access to a few common resources can get a new business off the ground in a matter of hours (minutes, for some). However, building a massively successful startup that grows into a mega-corporation (grossing hundreds of millions to billions of dollars with healthy profit margins that goes head-to-head with industry behemoths) is a different game altogether.

Bluntly speaking, most self-proclaimed entrepreneurs won’t do what it takes to build such an entity. It has very little to do with intelligence, subpar credentials, or limited connections; there are simply some sacrifices and investments most entrepreneurs just aren’t willing to make. In case you’re wondering what separates good entrepreneurs from the ultra-victorious, these are the steps likely preventing you from achieving that elite level of 0.01% success.

And yes, I did corroborate this roadmap with my $500M+ friend who “single-handedly” built one of the fastest-growing public companies in his industry, so this isn’t just an observation-informed opinion, but rather a proven playbook (with billion-dollar results).

Step 1: Why the 20-somethings don’t stand a chance

I’m not claiming it’s impossible to build a mega-startup in your 20s…but for most who try, you’re severely disadvantaged. Oh, it has nothing to do with immaturity, limited financial resources, or a lack of decades-honed connections. Instead, it has to do with two factors: time and patience.

I’m not referring to the time or patience a founder is willing to dedicate to their blossoming venture. We can all fall in love with our “next big thing” startup and spend 25 hours a day toiling away at it, determined to do “whatever it takes” to make it successful.

Here’s the problem: Sometimes “whatever it takes” is beyond the scope of our capabilities due to the sheer lack of time we’ve had to learn, experience, and master our industry — that is, unless you’ve been hard at work since pre-adolescence. Compare that to my $500M friend (“George”) who started his biggest (now public) company after two decades steeped in mastering his industry, interfacing with parties in every key role, and gaining exposure to enough aspects to poke and see the real holes.

Starting a billion-dollar company wasn’t an accident on George’s part, but it also wasn’t spawned by a desperate longing to be a founder. George was — and still is — an incredibly curious person, and he’s spent the entirety of his career questioning the status quo and seeking opportunities to improve it. That, by the way, is the definition of the entrepreneurial spirit: It isn’t someone who wants to “be their own boss” or “work from anywhere”; it’s someone who meticulously, continuously seeks out inefficiencies (or subpar products, services, or systems) and ways to improve them.

A 20-something invariably has far less time mastering, studying, or investigating an industry, discipline, product, or service from the inside out. Thus, in order for a 20-something to go head-to-head with the likes of my friend George, they’d have to make up for their lack of experience with a holistic industry deep-dive that few will have the patience to truly master.

Point being, it’s incredibly difficult to make up for 20 years of experience in a month’s-long crash-course, but a founder who hopes to make a billion-dollar splash should expect that someone on their core team — if not they, themselves — will need to bring that supreme industry expertise.

Steps 2 — 4: Where today’s founders go wrong

I mentioned that my friend George spent decades first-hand studying his industry, searching for holes, and seeking innovations to improve upon those inadequacies. Along those lines, the second way most young founders today go wrong is by failing to actually improve upon the current household names that run their respective industries.

2. Innovation

You can build a $2M, $10M, maybe even $20M company with great branding, a large and engaged social media following, and/or a healthy marketing budget around a useful product or service. However, you’re unlikely to build the next Home Depot if you don’t make a significant and marked improvement and innovation to the home improvement industry.

In other words, too many founders are building companies for the sake of freedom and the lure of fast cash, but fail (or neglect) to innovate or improve anything material in their industries.

3. Shortcuts

The third shortcoming stunting founders’ success (and keeping them capped in the millions, not billions) is the propensity to rely upon shortcuts. The explosion of AI, automation, and cheap outsourced labor has only exacerbated this entrepreneurial trap. In the name of being techy, forward-thinking, efficient, and hyper-scalable, so many founders (I’ve been guilty of this myself) have chosen speed over quality — and many of their startups have suffered the consequences.

While building automated, cost-efficient systems is a great strategy for scale, it shouldn’t replace the human input, expertise, and painstaking detail that often goes into crafting the first iteration of a world-changing company. The world doesn’t need another circle-jerk of AI-powered digital clone companies that add very little to the conversation. Shortcuts can help you scale, but they shouldn’t be a substitute for the most crucial stages of a startup’s infancy.

4. The ninja combination

The fourth misstep plaguing many young founders’ journeys is a combination of ego and impatience: What my friend George had, that so few new founders possess, is a confluence of humility and audacity.

He had the humility and patience to willingly accept that it could take decades to achieve any semblance of materiality and staying power with his new industry-disrupting startup. For context, George’s startup took close to five years before gaining significant traction and another five before hitting exponential growth. Simultaneously, George had the audacity (or relentless drive and unwavering faith) to climb that mountain anyway, despite the megaphone-wielding industry incumbents shouting that his innovation would never work.

On the off chance you were one of the few aspiring founders to beat the odds and master steps 1 through 4 of the $500M formula; you still likely aren’t enough to hit that 9- or 10-figure mark and become a mega industry disruptor like George. Here’s why:

Step 5: No, you aren’t enough

As a proud solopreneur (who’s also worked with co-founder-led startups backed by traditional investors and advisory boards), I hate to admit this limitation, but it’s the truth: When it comes to disrupting an industry and building the “Home Depot” of your space, that can rarely be accomplished alone.

If you simply want financial freedom and the title of “entrepreneur”, there are better-suited routes to take than aspiring to shake up an industry and create a new household name. If you do have 9+ figure aspirations, achieving them will likely require attracting large industry players and influencers to join your team for significant credibility, to accelerate growth, and to take any meaningful market share.

Simply put, no, you likely aren’t enough, and achieving George’s $500M+ net worth requires acknowledging and leaning into that from early on. George built his board of directors before he built his company’s monetization system, and that wasn’t by mistake.

Why most entrepreneurs will never be George

Achieving financial independence through entrepreneurial success versus George’s $500M+ level of accomplishment are two very different things. You don’t have to want to be an industry disruptor, to recruit a board of directors, or to make a meaningful, historic mark on your industry. If you simply want to be self-sufficient enough to maintain 100% control, scrappy enough to leverage your own resources, and nimble enough to see fast progress at your own hand, then building a public company like George’s probably isn’t your best bet.

Here’s the bright side: George’s entrepreneurial career didn’t really start until his 40s and peaked in his late 50s…so if you’re still kicking, there’s still time to decide. For now, build the venture that best suits you today, and know that we don’t all have to — or want to — be shareholder-answering CEOs. There are benefits to entrepreneurial anonymity that people like George can’t get back, so choose your journey wisely, but know there’s always room to pivot.