What I Learned Moving from Corporate America to Entrepreneur

October 12, 2022 Stan

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In a few frenzied career years, I went from a glass office overlooking Central Park, to getting my MBA from Wharton, to a string of Silicon Valley tech startups.

Now I’m acquiring and improving trailer parks in Iowa, Oklahoma and Texas, among other places. Our social mission is to expand the supply of affordable housing. My blue suits are packed away. My fingernails get dirty.

And I couldn’t be happier.

This is the time of year when thousands of new finance and business school students file into university lecture halls with dreams of big careers. Most are expected to go the traditional route — Wall Street, the business consultancies, the corporate ladders.

But I’m here to say there is much pride and satisfaction — and even prosperity — for business students willing to forgo the well-worn white gloves of finance for something grittier. I’m my own boss. I have more responsibility and less bureaucracy. I’m making and managing something real here.

If you think a little differently — and if you’re willing to take a chance, putting your own skin in the game — then the rewards of going your own way are well worth it.

Here are four key lessons I learned while switching from a corporate career to entrepreneurship.

Value is about numbers, not glamour

Like many in business, I’m a fan of Warren Buffett‘s philosophy of finding and sticking with undervalued assets. Lately, he’s found value in high-prestige giants such as Apple, Chevron, Paramount and big pharmaceuticals.

I applied the same value philosophy to real estate, where I started looking at traditional apartment buildings but then kept finding, buried in the listings, mobile home parks undervalued by 20-25%. This was not the asset class I had set out to investigate. In fact, at that point, I had never set foot in a mobile home park. The numbers always speak, though. You just have to hear them, especially if the numbers are talking in unexpected ways.

Entrepreneurship is for people who don’t follow the herd

Believe me, nobody at the country club is bragging about owning trailer parks. If you were one of the kids who always wanted to fit in, to wear the same clothes as everyone else and join the same fraternity or sorority, then going your own way as an entrepreneur may not be for you.

You have to be comfortable enough in your own skin and confident enough to go your own way — to do something in the business you believe in, regardless of what others think. You also need the fortitude to stick with it, even after the doubters weigh in. Entrepreneurship is not for people who like to play it safe.

Be honest about what you don’t know — and then work to fix that

Even if the investment numbers make sense, you have to know what to do with them.

The reality was that I knew little about the operations of mobile home parks when I got into this industry. Business schools tend to keep you focused on running spreadsheets and drawing up marketing plans — there were no case studies on mobile home parks in my curriculum at Wharton. So I attended seminars, read every book I could find and assembled an unofficial advisory board of 10 people who had owned parks themselves. I then asked a lot of dumb questions, and eventually better questions, and my discovery process revealed an overlooked asset class and better ways to manage it.

Understand and embrace the new culture

The numbers in your business may be compelling, but spreadsheets alone don’t make businesses work — people do. No matter where your MBA came from, a successful entrepreneur must meet employees and customers where they are.

I’ve traded shiny loafers for dusty cowboy boots and I hire people without a fancy college credential like mine — or, indeed, any college credential at all. The people in the field who manage mobile home parks may have different life experiences than the people who manage corporate offices, but the job is still about keeping a team on track to meet goals.

Communication skills are key. A successful entrepreneur must be able to give clear direction to the wealthy investor as well as the entry-level employee. You also need to be able to listen and learn. Book learning may give you the basics in a new sector, but so many of the toughest lessons come from experience in the field.

Entrepreneurship is not for people who covet the conventional bounties of corporate success. My company name is not up on lights on a skyscraper; I don’t have stock options; and a large human resources department is not negotiating my healthcare plan or matching my 401(k) contributions.

But the decisions here are being made by me, not by some person I’ve never even met in a faraway office. This is my vision, my plan and my responsibility. The result is mine. And so is the pride — and satisfaction.

Turning from corporate America to entrepreneurial America is a road less traveled. But there’s plenty of happiness outside the traditional business freeway for people with the desire and ability to turn their own steering wheel.