Entrepreneurship: I Did It “My Way”

My Pop loved Frank Sinatra. It was always playing in the store, on the porch, or in the barn. He used to joke that we had the most sophisticated and cultured horses and cows in all of Mississippi, because they knew all the lyrics to Sinatra’s masterpieces. 

One of my Pop’s all-time favorite Sinatra songs was, “My Way” - an epic ballad that I often come back to when feeling crushed under the weight of blazing my own trail. 

Here’s a selection of lyrics from Sinatra’s My Way:

Regrets, I've had a few

But then again, too few to mention

I did what I had to do

And saw it through without exemption

I planned each charted course

Each careful step along the byway

And more, much more than this

I did it my way

The Cold Hard Truth About Entrepreneurship 

Entrepreneurship isn’t easy, and it isn’t overnight. It’s a long, arduous journey that reveals a lot about you, much of which you may not have wanted to know. The process of pain and loss and struggle make you better, if you step up to meet the challenge. Many people tap out. I thought about doing so myself more than once. It’s hard, discouraging, and at this point, rather counter-cultural. 

Most people in my generation won’t take a gamble on their own business. The siren call of quasi-certainty that employment offers is too seductive. Self-employment would require sacrifice and a ton a stress - stress that you can’t just blame a boss or coworker on and pour yourself another drink. Successful entrepreneurship requires full accountability for everything - yourself, your success, and all your failures full front and centered. It’s not a pleasant experience, but, it can be incredibly rewarding. 

Yes, there were times, I'm sure you knew

When I bit off more than I could chew

But through it all, when there was doubt

I ate it up and spit it out

I faced it all, and I stood tall

And did it my way

Meeting the Challenges of Self-Employment 

I wasn’t really prepared for self-employment. We started a company when no one would hire me or my combat veteran spouse after the war. Our entrepreneurial future wasn’t really promising - no network connections, no access to capital, no back-up plan. The very first business course I took, the professor responded to my questions by telling me I had “no business being a business major” and told me to drop his class. The first five, six years felt like stumbling in the dark. Nothing seemed to work. I’d have a few small wins here and there, but the cost of securing those was immense and pretty demoralizing. I stuck to my guns on our founding principles, all of which end up running pretty counter to traditional growth trajectories for new ventures in an Amazon economy. 

Government contracting introduced a whole new kind of challenge. When I started, the extent of my experience with the government was getting a government-issued ID. There was no on-the-job training or degree program. I read and read and read federal acquisition regulations, listened to podcasts, and asked anyone I could find who had any experience with government contracting for insights. Then I did the work - taught myself through excruciating trial and error how to write proposals, do business development, staff contracts, and grow a bootstrapped small business in a sector very much geared to large corporations. The past few years of work have been painful, humbling, and unbelievably frustrating. No vacations, no holidays, no time off, but eventually, the culmination of my efforts paid off. 

I've loved, I've laughed and cried

I've had my fill, my share of losing

And now, as tears subside

I find it all so amusing

To think I did all that

And may I say, not in a shy way

Oh, no, oh, no, not me

I did it my way

David vs. Goliath: Small Business Start-up

Reflecting back, I can now see how the process shaped me into the person I needed to be to accomplish this goal. I’m sure it would have been easier to just polish up my interview skills and get hired by my now-competitors when the economy turned up. But I didn’t. My Mama always described me as a “square peg trying to fit into a round hole”. The way that everyone else takes never really fit me. So, I do it my way. 

I love challenges, especially when folks tell you it's impossible, such as starting a government contracting company from spare change. While it is certainly David and Goliath - a small disabled veteran-owned business versus the mega-primes - let us not forget, that David did take down Goliath with just a pebble and a slingshot. It can happen and it does happen…if you do what it takes to achieve it. Most people won’t; hence, my competition at this stage in the game is pretty thin. 

For what is a man, what has he got?

If not himself, then he has naught

To say the things he truly feels

And not the words of one who kneels

The record shows I took the blows

And did it my way

There are a lot easier ways to forge a professional future than entrepreneurship. There are days that I think It took the most difficult of the available routes within self-employment; however, it’s not without a few sunset views along the ascent. I have to change, develop, and push myself to make each milestone. It doesn’t really get any easier, the farther you go - the challenges are just different, and thus, you have to learn how to cross those chasms in a way that you can do. 

Lessons Learned From Doing It My Way

What worked for everyone else didn’t work for me. I got screwed trying to subcontract (repeatedly) and only ended up winning anything when I stuck my neck on the line, primed, and won it in open competition. I couldn’t stand the city, so I forfeited life in the public sector hub of DC for a quieter pace in the mountains and then had to figure out a new approach to business development from the cabin. I didn’t have degrees from the “right” schools, no strategic connections to Who’s Who, and no outside investment options to infuse cash into my start-up. On the checklist of “entrepreneur prep,” I came up lacking in all fonts except for my willingness to work my butt off, learn things I didn’t know, and see it through - even when it didn’t look promising. 

Yes, it was my way

And it worked. My company - the one everyone said “didn’t have a chance in hell” - now holds multiple multi-year government contracts. The big primes that refused to hire me or my spouse after the war reach out to us to be our sub. The folks who told me I didn’t come from the right schools, the right networks, the right whatever, now ask me for work. While their way certainly had consensus in a society built around being a cog in the employed wheel, my way offered me a different experience - one that came at a high cost and (eventually) rewards. 

Entrepreneurship has a high barrier to entry, especially in government contracting. Just because it’s difficult to get started doesn’t mean it’s impossible. If you’re interested in charting your own course via self-employment, I’d highly encourage you to do the work necessary to make your venture a success. Small businesses were once the lifeblood of our economy, and the benefits of this community investment are only possible when more of us opt to do it our way.