Why success doesn't feel good

As we try to climb the mountain that goes up and to the right, we sometimes hit potholes in the road. Combined with social media's continual assertion that everyone else is doing better, this makes us feel unnecessarily bad.

Why success doesn't feel good
The road that goes up and to the right contains potholes

We founded Yellowbrick back in 2014, and got things humming in 2015. We had a product to really sell in 2017, at which time Jason Snodgress our COO and I were already running much of the business together. We have a brilliant management partnership that continues to the day, one of us focused on doing the incredibly boring things (finance, processes, operations, metrics, etc) and one of us doing the interesting things (building software and selling things). Although we've had ups and downs along the way, once of the things is, no matter how well we do, it never feels good enough. Right after celebrating an event, many a time we'll find ourselves feeling a bit down in the dumps, drinking one too many of Jason's artisan Old Fashioned cocktails, thinking about all the things that are still broken in our business that need fixing.

As one of the best bosses of my entire life, Jon McCormack stated - now I don't just fix broken companies, I create them too. Jon's a very successful executive and if he can feel this way, anyone can. We've already built an incredibly successful startup at Yellowbrick - ARR in the multiple tens of millions, dozens of ecstatic customers, lots of high-value money raised, fabulous employee retention, and again - loads of customers that love our stuff. We've hit a number of major bumps along the way, from fundraising Series A to being forced to modernise the sales force because of the coronavirus pandemic. These major bumps are infrequent and each one presents an opportunity to find new advice, learn, grow and fix. However minor issues present themselves almost daily and there's always something broken. Someone's organisation is failing to work well, a release ships with bugs we shouldn't have let through, someone goes off-message so a customer pitch isn't as smooth as expected, bad collateral with daft messaging escapes review and makes it into the wild...

In a start-up, there are always things that need fixing and things that need improving, but it's the never-ending stream of potholes grinds on you. This is a job that can kill relationships, cause parents to miss their kids' teenage years, inflict regular insomnia, and make free time so rare that free time itself becomes an alien, guilty pleasure that we feel ashamed to tell others about on the offchance we enjoy it. Each time we hit a new pothole, it feels like checking into a new hotel only to find someone else's pubic hair in the bar of soap. It's not forgiving.

What compounds this is that whenever we look at the news or LinkedIn, literally everything is going up and to the right. Every startup is 'killing it.' New customers are being won all the time. Money is being raised at crazy valuations. Record customer deals in every segment are being won daily. Every VC's company is just 'awesome' and 'hitting the ball out 0f the park.' We only ever see others' good news posted to LinkedIn and social media which – just like in the world of personal social networking – makes us feel crap when we compare ourselves to everyone else. We hear everyone else's good news, but bad news is only from us internally. Why can't we IPO like Snowflake, win customers worth hundreds of millions a year, raise hundreds of millions at valuations of billions like Databricks, and be featured in every mainstream media known to man, and win all of Wall St while we're at it, because everyone else is doing that, right? Nope...

Recently I had an employee ask me how our last fundraising round we were only worth in the (very) high hundreds of millions, not the billions. We'd executed well to recover from one of our potholes, done a round at really good valuations, yet the employees didn't feel great. Vapourware companies with no revenue were worth billions now, yet we were here, growing around 2x year-on-year, and not worth as much, what gives? It turns out when you talk to most VCs, all their startups are doing great right up until the day they die. The failed investments don't get posted on LinkedIn. I've personally angel-invested in three startups, all of which had famous other investors like Andy Bechtolsheim, Khosla and GV folks involved, all of which made it through Series A and beyond. Two became worthless and the third got acquired for just enough money to pay back later preferred shareholders. Zero return, and nobody noticed.

What limited research I've been able to conduct shows that apparently only 1 in 12 entrepreneurs succeed at building a business, then 75% of venture backed startups fail. As of today, about 1% of funded startups can make it to be a "unicorn" although this percentage is slowly increasing as we continually print more money and make it available to investors. So here at Yellowbrick we're clearly in the top 2% of all startups, success-wise, and heading for the top 1% or more. This means we should all feel pretty damn good and proud of what we've accomplished and where we're going. Being in the top 10% is great, being in the top 2% is fantastic. We can't let human greed and media influences get in the way of what's already a wonderful achievement. Mega valuations are being driven by mostly by monetary policy, only partially by the success of the companies concerned.

Well, I've said my piece. I'll be off to bang my head against the wall once more, and start fixing the next thing. I'd love to hear from any others that feel this way, manage it on a day-by-day basis and yet somehow keep moving too...