I've been working on startups since the late-90s in NYC, SF, London and (now) Atlanta. I have dedicated my career to launching new ventures (both mine and those of others).
There's nothing that inspires/fascinates/excites me more than taking an idea from just a note on a napkin to a sustainable business that customers love.
I have a track record of success and failure that has given me a well-rounded view of startups and now want to give back to the community that has supported me so much.
You can see my public work history on LinkedIn, but here is my track record that you won't see anywhere else...
Startup attempt #1 - Failure (1997)
I would imagine that every entrepreneur has one moment early in their careers where they say "this company-starting-stuff doesn't look too difficult...I'm just gonna quit my job and do it!" For me that time was 1997 in San Francisco and I was three years out of college.
After 80-hour Investment Banking weeks in NYC, I moved to SF to start a company with a college buddy. We decided to launch a new venture because the lifestyle seemed fun - a terrible reason btw - and we literally did everything wrong. The idea/space wasn't well vetted. Our execution was bad. We never made any real progress. For all intents & purposes we were "playing startup." Over the years I've come to realize that this was a necessary part of my startup growth.
Startup attempt #2 - Failure (1999)
I would recommend that anyone who plans to dedicate their lives to startups should have one early experience with a well-funded, high-growth startup. This was Kozmo.com for me in 1999.
This new delivery startup was launching in NYC and they wanted to hire someone to launch new markets for them. So for the next two years - as we raised & spent $280M - I launched a dozen US markets and London for the company.
If you want a glimpse into what the first Internet boom was like, E-Dreams (short version here) is about the rise & fall of Kozmo. Even though Kozmo is a poster-child of this unsustainable period, I learned a ton on someone else's dime as one of the first non-founder hires.
Startup attempt #3 - Failure (2001)
When Kozmo ended, I slept for three months on a yoga mat on the floor of a friend's apartment in Queens (true story) to write a business plan for an idea that we ultimately decided not to launch. I had just spend two years on a rocket ship, so some quiet analysis was just the thing that I needed. And I consider it a sign of maturity that we decided that project wasn’t worth launching. I was growing.
Startup attempt #4 - Lifestyle business (2007)
After five "fat & happy" years in a big company’s Corporate Development team, I made my 4th attempt at a startup. Towards the end of my stint at Bigco I was doing some work on some disruptive Wi-Fi business models, so I decided to launch my own Wi-Fi company called SkyBlox a few months after leaving.
I was back on my own and created a business that over a hundred customers purchased...as long as I was the sales person. It wasn't a great idea, but it wasn't a train wreck either. Like a lot of startups, there was a 5% chance that something big could happen, but after 18 months it was clear that SkyBlox was an owner-operated lifestyle businesses.
Startup attempt #5 - Win (2010)
I consider the last six months of SkyBlox to be the most magical period in my startup journey. SkyBlox was good enough to sell to some customers, but it wasn't going to be a big business. But it got us thinking a lot about how local consumers hear about local merchants. We became absolute experts in local print, TV, radio, coupon books, etc...if local merchants used it to drive new customers, we knew the cost and efficacy. So we were now experts in a particular space and we were working our asses off. That combination put us in a good spot to be lucky.
My 5th attempt at a startup was a winner. Scoutmob took-off immediately upon launch. We doubled revenue every year for five years to millions of dollars, raised millions of dollars in venture capital, acquired millions of customers across the country entirely word-of-mouth (with no marketing staff or budget) and reached profitability.
All-in I've had one success under my belt and (at least) four failures...just about par for the course for this line of work I imagine. I'm confident that each "failure" was a necessary step in the education that would ultimately lead to future successes.
Of course, not everyone follows this exact path, but I would wager to bet that most successful entrepreneurs have their own early train wreck, lessons learned at another startup and (at least) one other "failure" before becoming the successful founder that you see today.
As you read my blog you can (at least) know that my thoughts are informed by many years and many stumbles.
As they say...
Good judgment comes from experience. Experience comes from bad judgment.
On top of all of this, I've had thousands of casual advice sessions over coffee with founders in the last few years. I also officially advise a handful of startups that have raised a great deal of venture capital and had some large exits. So (in addition to my personal experiences) I've also had many years of advising other founders.
Currently I'm working on the Switchyards Downtown Club, a consumer & design-focused startup hub based in Atlanta. I believe this type of model is key to creating more winners in less mature startup cities.
I've spent the better part of 20 years working on startups and thinking about what makes founders successful. You can reach me privately at email@example.com or discuss any of these topics publicly with me at @davempayne.
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