…and it is just getting started.

The days are bleeding together. One day flows into the next and the religion of strong late morning coffee to drive away the fogginess of sleep depravation has claimed another late night as a convert. My spine aches from seemingly endless hours in this chair slouched under a desk to low for my long legs. Fighting the lure of distraction I check my email, answer 3 or 4 support tickets that have come in since 4am when I finally carefully made may way into bed as to not wake Sally.  As the coffee takes hold and my tired brain makes an effort to assemble the mental checklist of the days tasks ahead the inevitable smile of content creeps across my unshaven face as I look at the sales numbers for the day before and behold the miracle that is the graceful sweeping arc up to the right of month over month sales.

So begins another day in the life of my bootstrapped startup, our budding overnight success 8 years in the making.

The red pill

In 2003 months after college I embarked on a journey with a single minded purpose; retire at 35. After reading the book Rich Dad, Poor Dad I knew that working for someone else was not going to bear the quantity of fruit I was seeking. I started a web design agency using the only non blue collar skill I knew and enjoyed a measure of success through 2006 ramping to as many as 7 employees for a time. Dumb luck and crystal ball like timing got me in and out of the booming Phoenix real estate market with a tidy profit. I made the first attempt at moving from service work to a product based business with a party planning social network we developed. Shortly after we doubled down with our own seed money and tried again with the prototype that would later become page.ly. In early 2009, burning up savings but long on hustle I forwent all but a few consulting clients to focus strictly on the product. November 2009, a few months after page.ly was launched and barely earning enough to cover the cost of the single server it ran on we were at a crossroads.

I knew with time the little seed of a business we planted would blossom but there was a fear we might bust before the harvest. Low on energy, and very low on patience with this our 3rd go at a startup we set a deadline for April 1st 2010. If this business didn’t cover it’s existing expenses and have enough for me to take a small salary we would pack it in and I would do the very last thing any entrepreneur wants to; admit defeat and get a “real” job.

Spring came with a good vibe that proved the adage: patience is a virtue. Taking a salary from the business now we had to double down and reinvest everything else. May thru August delivered consistent 22-45% growth month over month. Hot Damn I think we are on to something.

Some days I focus on business administrative tasks, most I write code in 12-15 hour unbroken blocks improving the system and automation.  If our first year was all about the product our second year now is all about driving exponential growth.

Lessons so far from the rabbit hole

Along the way I have learned some lessons and have been disappointed by some friends and blown away by the willingness of complete strangers to offer to help and evangelize our brand with everything in between.

The greatest thing about doing a startup, is choosing one people like to like. They love  it and do everything they can to help others love it. These people are a godsend to a startup or any business for that matter. They may not even know you as a person yet they saw value in your product or service and they evangelize it like a missionary on a pilgrimage. We are so fortunate to have created a brand/product that people seem to like to like.

The second greatest thing about doing a startup I have found is converting a hater into customer. There is always that person that just wants to hate your product, because they cant understand why you would charge money for something they feel they could do themselves or some other reason they pulled from their box of troll tactics. That conversation with them (perhaps after some of your community has extolled your products virtues on your behalf) where you take their hand and walk them through your value proposition with personal attention and patience where they do that 180 turn around and become your newest customer and community cheerleader is something I cannot get enough of.

The third greatest thing about doing a startup is the direct line between your efforts and the thickness of your wallet and the total freedom of the entrepreneur to do as they chose. You have absolute control over your time, how you chose to spend it, and the rewards you reap from it. The personal discipline it takes to stay focused and not be distracted is measured on a scale that sadly most do not possess. The traditional moving away from pain motivation people utilize will only keep them at even, or in this economy less than even. Every successful entrepreneur I know leverages moving towards pleasure motivation to carry them up and above that even mark. That new Audi or that coveted inc.500 listing, something is pulling the successful person towards the goal. If you only do enough to keep your ass out of the fire, and not find the internal fortitude, motivation, and discipline to consistently reach for the next step, your ass will always be getting burned. Some people never learn to take control of their own time as they are so conditioned to be told how to spend it.

A less than awesome thing about doing a startup is the toll it takes on you physically and mentally. I offer daily thanks to the body shape defining genetics I was blessed with as my lack of exercise and poor eating habits have not added more than the 10 extra lbs. I have amassed since college. Sitting in a chair in front of glowing led screen for hours a day is not going to win you any Mr. Universe titles or burn off the calories from the beers you had at dinner. The stress that comes with making the gamble of a lifetime is not easy to bear for some either. We were all (nearly all of us anyways) taught to go to work, collect a paycheck, and pay your bills. This system has been the backbone of the American economy since the industrial revolution and our schools are agents of indoctrination into that mindset. Trying to unlearn that is not easy for many. Wonder where your next paycheck as an entrepreneur is coming from to pay the mortgage? See the third greatest thing above. That uncertainty is not for the feint of heart.

Sadly I have found that some you may think that would be most solidly in your corner and ready to help you succeed seem to offer little more than dismissive reminders of your possible failure. I had a business/personal coach I worked with for a year or so and he always preached that “when you are moving forward those around will likely try to hold you back”.  They don’t consciously want to see you fail, they just subconsciously don’t want you to succeed before they do. In my life I have changed my friends and colleagues many times, each time moving toward a group that offered a new level of business saavy or encouragement. I think it’s normal and just something you do as you grow as a person.

Get your fix.

Why bootstrap? Why not? We gave a half-hearted effort early on to seek some capital and have at least done a mental exercise every quarter since revisiting the idea but always come back to the same place; it just takes too much time to chase the money when instead we could be earning it (building/promoting the product). That and no one bets on an unproven horse. Fact. We have to succeed before anyone is likely to invest and by then we don’t need it. In addition Sally and I have talked about it a length and we are not sure we want to be that kind of business. When did lifestyle business become a bad word? If your lifestyle is financed by a few million a year in high margin recurring business revenue how is that a bad thing?

We are just boarding the express train heading up the curve looking back at the chasm we just crossed. The mainstream customers are coming daily in increasing numbers and I see this manifest from the types of support questions we are fielding now. These next 2-3 years will see us climb up that bell curve towards the peak. We’ll have options along the way to exit early or keep going, either of which we have decided are to far in the future spend many mental cycles on an exit. Early on we measured things in terms of days, then weeks. Today we talk about metrics in 90 day cycles, with a eye out on the horizon beyond that a bit but not too far out as that seems like a loss of focus on what’s in front of us.

Everybody’s doing it

Depends who you run with I guess but everyone I know is working in or for startups. Well not everyone, some are still in the service/consulting business but I know their heart is the product space. While it may be in vogue it is more a matter of necessity I think in this economic climate. If this recession and bubble burst has not proven that the game is rigged against the working man to everyone with a brain cell I don’t know what will. People are taking their future in their hands and making a go of it for better or worse because the consequences of failing cant be any more damaging than standing in an unemployment line as a 99’r with a foreclosure notice under your resume.

And finally

This has been a brain dump of thoughts bouncing around in my head for a while as I have been feeling introspective and reflective of late soaking in this small taste of success from our 8 year grind.

There have been times I wanted to give up. Times I wanted to cut someone. Days I shake my head in disbelief at the high school games people play in business. Moments of sheer ecstasy and marathons of stress. Minutes spent in disappointment of those to show the smallest bit of respect and gratitude in return for my time and energy given to them. Hours of great conversation with smart and well meaning mentors. And a whole lot of time in between those other moments where I just had to dig deep and grind it out hoping someday it would pay off.

A friend of mine measures his day in mental cycles, so whatever he can get out of his mental computer and down to paper or crossed of his list saves cycles that can be applied elsewhere. I have done that here. Took a short moment to breathe.

2.5 years to go until I am 35.  My life is a relentless push towards my goal. My motivation to succeed is unwavering. Time to get back to work.


This ‘thing’, this crazy entrepreneur-hacking-startup-think-about-it-all-day-and-night-never-stop-pushing-for-growth thing is like a drug. It’s been a trip indeed.

11 thoughts on “What a long strange trip it’s been”

  1. I love you honey. I has been a crazy ride but there is no one else I’d rather be on this roller coaster with. You are the zing to my yang, the moth to my flame, the peanut butter to my jelly, and the night owl to my early bird. You’ve taught me how to have fun while seriously trying to make the world better. I’m proud to be your wife, your business partner, and your friend. Here’s to the next 60 years of our wild antics. Xoxo.

  2. Great post, thanks. From the first time I saw page.ly I knew what a brilliant idea you had. As many have pointed out before, it’s not necessarily having a good idea that makes you a success, it’s executing and following through. Clearly something you’ve done both quite well.

  3. One of the other reasons to bootstrap is that it keeps you close to the product and the customer so you are less likely to become one of those soulless companies in which customer service is an oxymoron.

    By the way, I love your writing style.

    Josh Bulloc
    Kansas City, MO
    How can I help?

  4. Josh, this really puts a lot into perspective as my wife and I are attempting a similar endeavor. Not quite the success that you’ve had, but we’re hanging in there and growing readily.

    Thanks for the great insight & motivation to keep it moving forward.


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  6. Great post, thanks. From the first time I saw page.ly I knew what a brilliant idea you had. As many have pointed out before, it’s not necessarily having a good idea that makes you a success, it’s executing and following through. Clearly something you’ve done both quite well.

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