Leading Ladies - Leslie Bradshaw

When I think of amazing women leaders that I admire, Leslie Bradshaw's name is always at the top of my list. I was originally introduced to Leslie after she brought me on to the Nike Women Make Yourself Movement campaign and ever since then, I've followed her career and it's been a pleasure to become her friend. This feature for the Leading Ladies series has so many nuggets that you'll want to keep for yourself, but most of all, I hope you start to admire the outstanding lady, Miss Leslie. 

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HOW DID YOU GET YOUR START?

Humor me here with a little extra room. To date, I think I’ve had four starts.

When I was very young, the first “start” was about work ethic and discipline.

My parents emphasized the importance of education and hard work throughout my childhood, so I guess they technically gave me that first start. And by hard work, I mean getting up early on weekends to do work around our farm and not playing with friends during the summer until I put in a good lot of hours in our vineyard. Oof. Those were long days.

When I was 18, the second “start” was about distillation and intellectualism.

I made the decision to go to UC Davis on a full ride, only to decide two weeks in I did in fact want to go to the University of Chicago (where I had gotten in, but was admittedly intimidated by all the fast-talking, prep-school-educated east coasters). I did what it took to transfer and my educational experience at the UofC took me from a bright go-getter to a refined thinker, writer, and scientist.

And when I was 24, I combined the previous “starts” into becoming an entrepreneur.

I co-founded a company would go on to generate over $13 million dollars in revenue (without venture backing); racked up countless industry awards; ‘won the internet’ with creativity; and counted NASA, Nike, Intel, Harvard, Twitter, Google, and The Economist among its clients during my six year tenure as President and COO.

When I was 30, I “restarted” and took a big step back to recalibrate and get healthy.

I’ve shared at length about the process of finding my happiness and my health again, so I will keep it brief here: It was a critical that I hit “pause” in my life before I “restarted.” And when you read and hear a bit more about the why and the how, I think you will understand (and maybe even relate).

Lastly… I hope that I have at least a few more “starts” left in my career. And I am grateful to carry forward all that I’ve fought hard to learn and earn in the early “starts” (and “restarts,” too).

WHAT RISKS DID YOU TAKE?

I have turned down big jobs at big companies in favor for owning a piece of the action and building something from nothing. This has meant I’ve lived in six different cities in the last 15 years; I’ve rented furniture instead of owning; I’ve lived out of suitcases for months on end; and I’ve said goodbye to two loves I could have married.

But it’s been worth it. I admit that not every day feels that way, but panning back at the canvas of my life in epochs of months and years, it hits me like sunrise after a rainstorm. Pow. It takes the words out of my mouth and the breath out of my lungs.

I’ve built an incredible career with a syncytium of brilliant colleagues and loving friends all over the country. I am also becoming much better at balance, throttling, letting go, and being a good sister and daughter. Risky as they may seem to some, my decisions, actions, and accomplishments are what have brought me here… to this moment… talking with you Stephanie... and sharing my two cents with your community. It’s an honor.

WHAT IS SOMETHING THAT SCARES YOU? 

Letting someone down I admire.

LOOKING BACK ON YOUR CAREER, WHAT WAS A MAJOR TURNING POINT FOR YOU?

Like a lot of ancient millennials, I almost became a lawyer. Along side doctor, teacher, astronaut, and police officer that’s what we were told we could be. I interned a few summers at law firms back home (Oregon) and landed a project assistant job on the IP team at Arent Fox in Washington, D.C. when I graduated college.

There, five important things happened that would forever change the course of my professional life. Yes, five. Combined, they were my turning points. Stay with me.

One: I became an “Internet Watch” specialist. I learned about source code, meta data, phishing, and domain name squatting. It was awesome. Also: I reckon I did more mail merges and sent more cease and desist letters in one year than I have emails in my three email accounts right now.

Two: I didn’t like the two-tiered professional class vibe of the law firm. There were those who went to law school, and those who did not. And the older the former, the more they looked down upon the latter. The professionals vs. the paraprofessionals. No thank you.

Three: I became a volunteer member of… the new business team. I loved the act of crafting the strategy not only for the proposal itself, but also for how the pitch was going to go. I was a quick study in making well-designed decks, too. My billable hour quota suffered, but my sales savvy flourished.

Four: I worked under the leadership of Dave Gryce. To this day, we remain close and in my managerial roles I have continued to draw from his western, no-nonsense, genuine, straight-talk style. He reminds me a lot of my dad.

Five: I met my now friend-for-life Chris Olson. Together, we had to sort thousands of files and millions of documents. He was funny, hard working, and someone on which I could always count. When I was in the process of scaling my own company four years later, I brought him on as a lead strategist. And I would jump at the chance to work with him again, for the rest of my life.

WHAT ARE THREE PIECES OF ADVICE YOU'VE RECEIVED THAT YOU'VE CARRIED WITH YOU THROUGHOUT YOUR CAREER?

1. Do the work until it is done. Don’t talk about it. Don’t cut corners. Don’t give excuses. Don’t kick the can down the road. Just dig in and do the work. If you don’t know how, then figure it out. Ask. Make some calls. Partner. Stay late. Can’t is a four letter word.

2. Bring a notepad and pen to every conversation—and take superb notes. This has served me in so many pinches. What was said at that meeting last week? what were the action items? how did that diagram look again? Oh, that’s right, I TOOK SUCH EXCELLENT NOTES I CAN FOLLOW THROUGH LIKE A BAWSE. Amazes me to see people of all ages show up to meetings, conferences, and important conversations with nothing to capture what’s being said. And I am not surprised when those same people lack follow through and fail to advance at the speed of those who did and do.

3. You’re too grateful and you over-deliver. This was feedback given to me in an annual review when I was 23. I’ve taken it as the anti-advice. I continue to give thanks to those who help me, give me opportunities, and forgive me when I make a mistake. I’ve throttled down a bit on the over-delivering, as I’ve learned when it’s not needed, appreciated, or deserved—see my answer to the next one, ahem. But I still aim to service at the highest level of excellence and often that requires going above, beyond, and an extra mile or two.

BIGGEST MISTAKE?

Spending the last nine years dating “fixer uppers.” Building their careers behind the scenes while also building mine. It was always exhausting, often thankless, and never the right way to spend my time, energy, and social capital. But I vow to not make this mistake again (and my friends and family have my back). Good guys with your shit together: inquire within.