Denali, Alaska

Uncertainty is the Spice of the Startup Life

Joshua Henderson
3 min readSep 3, 2013


I discovered entrepreneurship when I was 20 years old, the summer before my senior year at Georgetown.

At the time, I was an undergraduate “Pre-Med” Psych/English double major studying for my MCAT and building an online textbook sales site that would skim affiliate revenue from click-throughs and send the 5-10% revenue share to a charity that supports children’s literacy.

I had no idea what I was doing, but I hired a designer, built the site, made it public, and then told my friends. I quickly learned that the Field of Dreams mantra, “If you build it, they will come,” doesn’t apply to startups.

So I began marketing the site more seriously and looked to surround myself with resources on campus and other student entrepreneurs in order to develop a more aggressive marketing plan to promote my venture. I didn’t find much.

I was disappointed in my alma mater. Disappointed that there wasn’t a community of people I could tap into, yes, but disappointed too, that I had only one year left to nurture this newly discovered interest in startups. I didn’t want future students to wait as long as I did. I wanted Georgetown to be the reason they started or joined a startup, not the reason they didn’t.

So I put the textbook site aside and made it my mission that year to build an entrepreneurial network across the university. I paired up with a friend in the business school, started an unofficial student group, designed a logo, bought a banner from FedEx (fake it until you make it), joined up with another fledgling club to found a business plan competition… and off we were. It was a great adventure.

When I graduated, I had a big decision to make about which path to take, medicine or entrepreneurship.

I could choose medicine, and make a commitment to the ten-year journey from med school to internship to residency to specialty. Or, I could choose entrepreneurship, despite having no real experience, next to no formal training, and no real idea of what the next year, let alone the next ten, might hold.

I jumped at the thrill of this uncertainty.

I landed quickly, and thankfully weeks before the market crashed in 2008. I joined Springboard as the Director of Programming and have spent the last five years building an entrepreneurial network at a global scale to support high-growth tech and healthcare startups, all led by women.

Uncertainty, I’ve learned, is the world that entrepreneurs live in.

When you’re building a company, there are always far more questions than there are answers.

Will my target customer buy our product? At what price? How many over the next five years? What other potential revenue streams can be exploited? When can we expect profitability? What if an indirect competitor moves into our space?

No one ever has all the answers. You can only build an efficient process for learning the answers as quickly as possible. It’s a core principle behind the Lean Startup movement: make something, push it out, learn, adapt, then repeat, as fast as you can on the road to building your money-making machine.

Entrepreneurs need to not only be comfortable operating in uncertainty, they need to embrace it and thrive in it.

Last week, I left on a plane from Washington, D.C., to Italy, where my wife Meghan and I relocated for the next several years for her position in communications with the U.S. Navy. I will be staying with Springboard, remote working on our programs and spinning out a for-profit company that will match entrepreneurial talent with paid business opportunities from growth-oriented companies needing solutions.

I’d never been to Italy. I’ve never lived in a non-English speaking country. I’ve never worked remotely for longer than a couple of weeks. I’ve never started a company.

I don’t have all the answers about these next few years, but to be honest, I prefer it that way.

Uncertainty is the spice of the startup life.



Joshua Henderson

1000% committed to helping women innovators transform industries, cure diseases, and build scalable businesses