If I Could Do It Over, I Wouldn't Start a Business

I've made good money in corporate tech and built a solid career in business. Most folks would say I've done pretty ok for myself. But if I'm being completely honest, if I could go back and do it all over again, I don't think I'd start a business.

I think I'd just work my corporate job and invest heavily in tech companies instead.

That probably sounds crazy coming from someone who's spent years building businesses and talking about ownership. But the more I reflect on how things actually played out versus how they could have gone, the clearer it becomes that there was probably a better path for me.

There's a narrative we tell ourselves, especially in Black communities where we've been locked out of so many traditional wealth-building opportunities. The narrative sounds like this: working for someone else is a trap, you'll never get rich on a salary, real wealth comes from ownership, so you need to start your own thing.

There's a lot of truth in that. Ownership definitely matters cause it builds wealth in ways that salary alone doesn’t. But I think we've conflated ownership with entrepreneurship in a way that's cost a lot of us time, money, and peace of mind.

Starting a business became synonymous with building wealth, when really it's just one path among many. And for a lot of us, myself included, it might not have been the best path.

When you're in it, you tell yourself the sacrifices are required because you're building something. But the real cost of entrepreneurship isn't just financial; it's time, energy and relationships. It's the mental load you're carrying every single day about growing your business, funding your business and about cash flow.

I missed time with my family that I can never get back. Building a business demands a level of attention and presence that leaves less of you available for anything else. There were dinners I was physically at but mentally still working through a business problem. Weekends that were supposed to be off but turned into catch-up time. Vacations where I couldn't fully disconnect because something always needed my attention. Or worse, vacations that I could not go with my family on due to business. I’ve also lost and damaged relationships because I handled some situations badly.

And the irony is that while I was grinding to build this thing, convinced it was the path to freedom, I was actually less free. When you work for someone else, you can leave work at work most of the time. When you own the business, the work follows you…everywhere

Here's what I think would have worked better for me, and what I think would work better for a lot of people who are good at what they do and earn good money on their job.

Stay in the corporate job. Get really good at it. Climb to a level where you're making great money that you’re happy with. This doesn't mean stay someplace you hate, but if you're happy with where you are and you’re making great money, don’t think heading for the entrepreneurial exit is your best move. 

What you can do then is take a significant portion of that income and invest it aggressively. Not just in index funds, though those should be your foundation. But also in private companies through angel investing.

Think about it this way. If you're making $150K, $200K, $250K in a corporate role and you're investing $30K to $50K a year into a mix of public and private market investments, you're creating opportunities to build big wealth without the stress and time commitment of running your own business.

When you do this, you’re getting ownership/equity through your investments. You're diversifying across multiple companies instead of having everything tied up in one business that you're responsible for keeping alive. And best of all you can do this while having a schedule that lets you be present for and in your life.

Let's say you stay in corporate for 15 years. You're making good money, you're disciplined about investing, and you're putting money into a diversified portfolio that includes both public and private investments like angel investments.

Over 15 years, your index funds should be compounding pretty steady. Your 401k and/or IRA are maxed out every year and growing tax-free. Some of your angel investments will fail, but a few hit and return 10x, 20x, maybe one returns 50x or more.

After 15 years of this approach, you could realistically be looking at a net worth in the several millions. And here's the key part; you did it while working 40 to 50 hours a week instead of 70 to 80. You had evenings and weekends. You took real vacations. You were present for your kids and others you love and care for.

Compare that to the entrepreneurship path where you spent those same 15 years building a business full time or even as a side hustle. Maybe it worked out and you built something valuable that you eventually sold. Or maybe you built something that pays you pretty ok but requires constant attention to maintain. Or maybe, like what happens to most businesses, it never quite got to the level you hoped and you spent 15 years stressed and grinding for almost none or actually no returns.

The business ownership path requires everything or most things to go right with a single business (yours), which means you're placing all of your bets on one thing. The investing path spreads your bets across dozens of businesses which means spreading out your risk and all it requires of you is to be patient and consistent.

This will work with any career but if you work in tech, this strategy has some unique advantages.

You understand the industry because you work in it every day. That knowledge gives you an edge when evaluating startup investments. You may know what good product development looks like. You may understand go-to-market challenges. You may be able to spot BS in a pitch deck because you've seen how things actually work inside tech.

Your network in tech also means you may have access to deals that other people don't see. Founders you've worked with who are starting new companies. Colleagues who are angel investing and can bring you into their deals. Or maybe industry connections you have can lead to early looks at promising startup deals.

And because tech salaries, especially at senior levels, are normally high, you should have the capital to invest without having to fund a whole  business yourself by taking out loans or other risks that could impact your family's financial security.

You're basically getting all the advantages of ownership through your investments, without having to carry the mental and financial weight of being responsible for a whole company's success or failure.

If I could go back and talk to myself at 25 or 30 years old, I'd be like...

Stay in corporate. Get good enough at what you do that you're valuable and well-paid. Don't coast, but also don't kill yourself trying to climb every ladder (unless being at the top is your goal). Be solid, reliable, and strategic about your career progression. But also know that they can relieve you of your job and any point in time.

Save aggressively from day one. Build an emergency fund, consistently invest in index funds for medium term returns and easy liquidity, max out your retirement accounts, then start allocating serious money to angel investments as soon as you can.

Learn how to evaluate startups and build a disciplined investment strategy. Be smart, spread your bets, and be patient.

Protect your time, energy and your health like they're your most valuable assets, because they are. Your kids are only young once and your marriage needs your attention in order to stay strong. 

Also remember that wealth isn't just about the dollars in your account, It's also about having options, time, and the freedom to be present for life today versus deferring it to the future.

I want to be clear about something. I'm not sitting here full of regret about the path I took. I learned a lot by building a couple good businesses and failing others😒and that's what helps me be a great investor in businesses today.

But I'm also honest enough to look at the tradeoffs and acknowledge that there was probably a better way to get to similar financial wins with a lot less stress and a lot more life balance.

And I think a lot of people who are considering entrepreneurship because they think it's the only path to wealth need to hear this perspective. You don't have to start a business to build serious wealth if you're smart about investing; and especially if you're in a high-earning field.

The corporate job plus aggressive investing approach isn't as sexy as running your own business. But it works, it's lower risk, and it gives you your life back in ways that entrepreneurship often does not.

You know what the real flex is? Being able to walk away from corporate work after 10 or 15 years because your investments have grown to the point where you don't need the job anymore.

That's freedom; and you can get there without sacrificing your nights, weekends or time with your family.

If I could go back, that's the path I'd take. I’d stay in tech, keep pulling down almost $400k a year. Invest aggressively and intelligently. Build wealth through ownership of other people's companies instead of killing myself trying to build my own.

Cheers,

~Abdul

Hey Hey… I’m Abdul I’m the chaiman of Ajo Angels and Shujaa Capital and I’m on a mission to introduce angel investing to 25,000 black folks over the next five years. I’m doing this with the goal of narrowing the racial wealth gap as well as trying to close the billion dollar funding gap for black founders.

This article reflects personal perspective and experience, not financial advice. Every career and investment path involves different risks and opportunities. Make decisions based on your own circumstances and goals.