I Secretly Built My Startup to 7-Figures Backwards; Here’s How I’d Do It Differently if I Started From $0

There are much faster paths to millions, entrepreneurial freedom, and happiness than the one I took.

I’m guessing you’ve heard the saying “Comparison is the thief of joy”, and while that’s perhaps true, it can feel like all we have. If we didn’t have more successful role models to compare (and aspire) to, we’d have far less vision for what’s possible with respect to our careers, businesses, finances, and lifestyles in general. That said, comparison can lead us astray — particularly when we believe there’s a fast track that turns out to be the riskiest, most anomaly-riddled path to where we actually want to go.

In the world of early-stage entrepreneurs, first-time founders, and startup-obsessed wantrepreneurs, it’s incredibly easy (and common) to get distracted and derailed down a shiny object-filled path under the guise of making “progress”. The problem lies in the fact that we all measure “progress” differently, and for many founders, even a decade or two of progress can leave them drained, depleted, and far from their financial and lifestyle goals, despite their ventures having the “trappings” of success.

What are those B.S. trappings of success that don’t necessarily get founders where they actually want to go?

Proof of concept
Funding
Customers
Industry awards
Profitability
Growth

But wait: How in the world can a startup have all of the above and still leave a founder unfulfilled, disillusioned, and wondering if they’ve been wasting their past 5, 10, or 20 years on a hamster wheel to nowhere?

That’s the pesky truth: Most founders are too ashamed to admit why they really got into entrepreneurship in the first place. With a bit of honesty, they might forge a much more direct, fulfilling, and authentic path. Here’s how I’d do things differently if I were starting over from $0…

Start at the end (not the beginning)

Here’s the truth most wantrepreneurs won’t admit: They know exactly what they really want, and it isn’t necessarily all too relevant to the business they’re building right now. How do I know? I was one of them.

Sure, I told myself — and those around me — that all I wanted was to “be an entrepreneur”, but in truth, I was running away from what I didn’t want, which entailed:

A toxic corporate office culture
The fear of getting fired
Having my time and location dictated by someone else

While I’m sure many of you can agree the motivation to flee those aforementioned aspects of many corporate jobs is valid, I don’t believe that alone is reason enough to cling to a startup as your savior.

In this day and age, there are many income-producing jobs, investments, and opportunities that eliminate those aforementioned dealbreakers without incurring the risk inherent in building a startup.

Rather than running towards entrepreneurship to escape the negative downsides of your current career, it’s worth asking a better question: What are the positive upsides you actually want in a future lifestyle and business?

Ironically, I knew my handful of dream goals, but I was too afraid to admit them to myself for fear of aspiring to something unattainable. Instead, I put those goals in the back of my mind and decided that success in startups was going to be my stepping stone towards those goals. In other words, I decided to use entrepreneurship as my lottery ticket toward the things I wanted most, without realizing I’d chosen the highest-risk, lowest-likelihood path to get there.

In case you didn’t know you had it, here’s a reminder that you have permission to want things other than VC funding, a TechCrunch write-up, and a unicorn valuation. In fact, you’re allowed to want seemingly selfish, even materialistic things, too. Would a healthy dose of altruism and a desire to improve the world potentially pay you dividends down the road? Sure, but at the end of the day, if you’re just doing something because you think it sounds good — or would look good on a resume, in a write-up, or in an investor’s eyes, the mask is likely to slip and your true motivations are likely to betray the facade.

Thus, rather than diving into a problem that needs to be solved or leaning into the obvious “best fit” industry opportunity for which you’re poised, start by asking what you really (selfishly) want, with no filter or judgment.

When I started my entrepreneurial journey, I was too wrapped up in the glorification of startup culture to admit that I wasn’t necessarily chasing industries I loved, problems I cared about, or products to which I’d want to dedicate years or decades of my life. I was selfishly, secretly chasing the opportunities I thought would yield a big payday that would finally allow me to consider what I wanted after all.

Collateral, assets, and passive income

The second biggest mistake I see countless first-time (and young) founders make is thinking they have to risk it all for their startup at the expense of their own financial security. Startups can be risky, but even some of the wealthiest, most successful founders promote the idea of leveraging “OPM” (other people’s money), rather than going all in with your own. This is an area where I almost became a sad statistic: A broke, failed founder who’d depleted my life savings on a series of ventures that left me destitute.

Well, I almost did, but thank goodness I made one smart move I’d have doubled down on if I could do it again: While I spent my early (pre-startup) twenties working on Wall Street, saving every penny and living a Dave Ramsey (beans and rice) lifestyle, I put my money in two places:

A savings account (the entrepreneurial runway)
An investment account I didn’t touch (I gave it to a financial advisor and considered it 100% under lock and key)

While I did end up losing 6 figures of my life savings on my first failed startup, I had one saving grace that put me decades ahead of my peers: That managed investment account was sitting there waiting for me, whether all my businesses failed or succeeded, cash flowing and growing, despite my own career foibles.

In retrospect, I wish I’d reversed the portfolio and put 2/3 of my savings into that account and only 1/3 into my startup runway. Here’s why: The more runway you have, the more runway you just may use. I know from experience, as the first business I built cost me 6 figures and never got profitable, while later ventures cost me under a thousand bucks and kicked off hundreds of thousands of dollars in passive income for years to come. Point being: Cash constraints make people scrappy, and scrappy people either get resourceful and efficient or fail trying.

For those of you wondering why hoarding money in that managed investment account was so crucial to my strategy — and why I wish I’d doubled down on it when I had the chance — here’s why: About a decade later, I was able to cash out of that account and put a down payment on a scarce real estate investment that instantly multiplied my net worth, while also providing a new cash flow opportunity at no additional cost.

Unpopular opinion: Risk less

I didn’t have to use proceeds from a business sale or comingle disparate ventures (or personal and business funds) in order to make this investment, yet it changed my financial life more than most of my startups combined in far less time. The moral of the story: Yes, you’ll probably need some personal savings to kick off your entrepreneurial runway; however, I’d set aside an off-limits fund purely for investments, appreciating assets, (that can be used as valuable collateral), and non-startup passive income opportunities. Being an entrepreneur doesn’t have to mean risking it all, and a smart founder-investor leverages the power of diversification.

The network and reputation: Humility sells

Among the many things I did wrong or backward in my entrepreneurial career, building a network and professional reputation (first) is definitely one of them! I did what most young, insecure, eager-to-prove-themselves entrepreneurs do, and I waited. I decided to attempt to build my businesses first, then, after a few homerun successes, newsworthy write-ups, or industry awards, I would stroll into the rooms of success and finally belong. Here’s the issue: I completely bypassed — and missed out on — the mentorship opportunities and the benefits of the underdog effect.

If you’re a young, new, or first-time founder, I implore you to start networking and building a professional reputation first in the spheres you care about, rather than working in isolation until you finally achieve an accomplishment worth bragging about.

People like to help people who share their journey, their humility, and their authenticity, no matter how green they are. In fact, I’d argue the young, green, ambitious, resourceful, pre-win entrepreneur can be more endearing than the solitary workhorse who’s finally emerged from their dungeon after selling a company, raising a funding round, or achieving profitability. Remember: Meaningful connections and fruitful business partnerships can take years to foster, and there is no fast track to conjuring up the relationships you failed to build, grow, and cement.

Passion produces profits (not the other way around)

To be honest, this is the biggest mistake I made — and one of the most common errors I watch founders commit every day: I built a business to fund my passions, rather than building a business around (funded by) my passions. As artsy and non-scientific as it sounds, the simple truth is that passions can produce profits, and it’s far easier to be supremely successful at something you love to do (or care strongly about) than it is to crank profits out of a venture that feels like a chore (ahem: an annoyance).

If you knew you would make the exact same amount of money and have the exact same degree of success no matter which industry, idea, or venture you pursued, would you still choose the path you’re currently on? Believe it or not, if you’re at the top of your game, invigorated by the work you’re so lucky you get to do that calling it “work” feels utterly ridiculous, you probably will be enthused to put in the extra hours. You probably will seamlessly do what it takes to grow the venture, expand, and reinvest your time and finances undeterred because it isn’t a chore; it’s your passion.

Busting the startup myth: It doesn’t have to suck

If entrepreneurship feels hard, draining, unfulfilling, or otherwise like actual “work”, you may be in it for the wrong reason, or perhaps you’ve fallen into the trap of building your empire backward like I did. Being an entrepreneur doesn’t have to feel like taking a major risk, sacrificing everything (including your long-term financial security), and delaying your greatest passions and dreams for the foreseeable years or decades (until your venture makes it big). I’d rather invest some more time figuring out the right path (while buying myself some financial wiggle room and security) than grind on autopilot down a path I can’t wait to get off.