What To Do Next...

The topic of pivoting is an interesting one. The word has taken on a new life in the world of tech entrepreneurship.

I learned how to pivot playing basketball in the 7th grade. Even then I found it a hard move to make without hesitancy. What would the consequences be? Would the other direction really better than the one I was currently facing? Would I expose myself to someone who would steal the ball from me? I could see the defender in front of me, but what was behind me?

Pivoting means you keep one foot solidly planted, so you’re not abandoning your current position, simply shifting your perspective and momentum. You have the same ball in your hand, pivoting just opens up the possibility of a better position to shoot or pass the ball.

As an entrepreneur, the urge to pivot hits me when things look dismal. For me, it is always driven by fear and doubt. Something isn’t working. What should I do? Is my concept fatally flawed? Has the market moved and I missed it? Am I just incompetent? Is this whole thing going down in flames with me in the pilot’s seat? This is where I usually land - I embrace the doom, blame myself for not being better, more creative, more connected, more in-tune with my customers. At this point in my internal conversation, my inner coach kicks in and starts reciting slogans I’ve read on inspirational posters and memes, “Winners Never Quit and Quitters Never Win”, “Its Not Important How Many Times You Fall, But How Many Times You Rise”, ““Success is not final; failure is not fatal: it is the courage to continue that counts.”

Unfortunately rah-rah slogans will only get you so far when you’re burning cash and so unsure of your next move that you’re effectively paralyzed…

The entrepreneur’s playbook says this is when you should start talking to mentors and colleagues, seek out the wisdom of others who have walked the same path. I prefer to show up with answers, not questions, so I struggle with this. After 25+ years in entrepreneurial companies, shouldn’t I be the one doling out advice?

This is where humility and vulnerability come into play.

“Okay Lea, its time to raise your hand and admit to the teacher and everyone else in the classroom that you’re completely lost.”

I know from experience that the only way out is to invite people I trust and value for their expertise into the conversation. My internal dialogue is fatally flawed, and the more time I spend in my own head, the worse I feel. In that negative emotional state I can’t move the needle.

Inevitably, picking up the phone and calling a mentor or fellow CEO or sitting down over a cup of coffee will do the following:

• Give me clarity on the real problem.

• Help me feel less alone - yes, everyone faces the same doubts and good mentors will remind you that you’re not that special.

• See options I didn’t see before.

• Shut down the voices in my head.

Do I need to pivot? Maybe. But maybe I just need to fake out my opponent and take a shot.

Let's Talk About Love For A Minute

What’s Love got to do It?

Everything. Because starting a company is a lot like falling in love. 

It requires you to be;

• incredibly vulnerable

• to take extraordinary leaps of faith

• AND the chance of heartbreak is high. 

Back in the summer 1990 I was preparing to graduate from my MBA program.  I wanted to be a commodities trader and I had made it to the final round of interviews with a large firm based in the Midwest. I grew up in Nebraska and knew the difference between soybeans and sorghum – so that environment felt comfortable to me.

And then I got a call from a small software company in Berkeley California asking if I wanted to interview for a marketing job. It was July in Phoenix - 115 degrees – a free trip to Northern California? – absolutely.

So, I headed to Berkeley, and over the first plate of Pad Thai I’d ever eaten, a charismatic entrepreneur named Brian Dougherty convinced me that his company, Geoworks, could beat Microsoft Windows in the operating system game. 

He didn’t talk about their 401k program or how many vacation days I’d get. Instead, he shared the love he had for his idea. He was going to democratize the PC, to make it easy for inexperienced computer users like my mom to do desktop publishing.

That I believed him tells you how naïve I was, but it also tells you how convincing he was.

It’s like that moment when you’ve been dating a perfectly good person, someone sensible, someone you can imagine a decent future with – and then out of the blue you meet another person who TOTALLY sweeps you off your feet.

Brian’s passion was infectious. By the time the check arrived, I’d abandoned my future on the trading floor. I wanted to be a part of Brian’s mission to beat Microsoft.

I went back to school all excited, to tell my friends who had landed jobs at places like Goldman Sachs and American Express that I was going to turn down a great job at a well-established company for a start-up that might not be around in two years. 

They tried to talk me out of it.  They couldn’t understand what was driving me, and I didn’t fully understand it either. Imagine trying to explain to your mother that you’re leaving your reliable, steady boyfriend to run off with the lead singer of a Styx cover band.

Nothing about it was logical.

That’s what happens when you’re in the early stages of a romance, with a person or with an idea.  You ride the wave of that feeling - logic be damned.

So I joined Geoworks and got a front row seat to watch a start-up in action. I saw how Brian used his passion to motivate the team, how he got people to give up their personal lives, to stay late and live on bad Chinese food. 

 We made impossible deadlines. 

 Passion can push you to step beyond your own fears and limitations.

Brian inspired me to set aside my fear of public speaking and demo PC User groups all over the country, basically stand on a stage in front of hundreds of hard core computer geeks and talk about software. I’m an introvert – the stage is not my natural habitat - but I did it anyway. At every demo I had to face that one guy in the auditorium who had shown up solely to ask a question I couldn’t answer. It was intimidating, but I was determined to do my part. 

That experience changed me. I became braver as a result.

What I learned at Geoworks and at various start-up companies over the next ten years was that the road less traveled was the road for me. 

 I didn’t need a job that was well-defined.  Because I had grown up in chaos – something I’m not going to elaborate here, it’s in my book – chaos didn’t bother me. I discovered that I liked the challenge of sorting it out. I could take on new roles and make things happen. 

I could bring my bravest self, and once you have been in a relationship that raises you up to a new level, everything else feels like settling. 

 Stay tuned for more….

Don’t Freak Out Today, Freak Out Tomorrow - A Short Guide to Surviving Entrepreneurship Part One

In 2018 I published a memoir called: Finding the Exit; It’s Not Where You Start, It’s Where You Finish. While talking to different agents and publishers, one asked me a question I could not immediately answer - “What are you an expert at?”  

My initial response was to tell her that I wasn’t an expert at anything. Expert is a strong word, not a moniker to be claimed lightly. She challenged me to think about it, “Everyone is an expert at something,” she said.

The next day, it occurred to me that perhaps I COULD claim to be an expert at one thing – not freaking out. Many years spent in small, fragile companies had taught me to maintain my composure and decision-making ability in the face of diamond-crushing pressure and odds that few seasoned gamblers would take. 

I’d survived eight years as an employee and executive in risky start-up companies, and eighteen as a founder-CEO without developing any ulcers. I’d mastered the art of the empty-eyed stare as investors outlined why my company would never make it, the deep breath in the face of impending insolvency and the internal stillness needed to make the next phone call or the next pitch to sell an uncertain proposition to investors, customers and employees. I’d figured out how to sleep at night, not knowing if I could pay my mortgage that month, and consistently answer the question, “How is it going?”, with a resounding, “FAN-TAS-TIC”, even when I wanted to weep. 

While my expertise does not carry as much gravitas as the ability to split atoms, perform neurosurgery or negotiate the release of hostages, it is a valuable skill for an entrepreneur.

I’m going to write it bit by bit in this blog. My hope is that entrepreneurs in the thick of it will find inspiration here or just reassurance that they are not alone.