Founder Feedback Year #4: It Actually Is About The Journey, Not The Destination

Stack 4.0 Celebration

Four years…I can’t believe how fast it’s flown by. Four years ago I left my corporate gig to take a risk on becoming an entrepreneur. It hasn’t been easy, but I’ve learned a lot in that timeframe and managed to share some lessons over the year’s: Year 1, Year 2, and Year 3. So, to keep my annual blogging tradition alive, I’m sharing five new lessons learned over the last 12 months while leading the StackCommerce team.

While we made great strides over the last year, it was no fairy tale. The lessons learned this year, frankly, are one’s that I am still trying to take in and fully accomplish myself. They are the one’s that if go unheeded, will hold us back from scaling to the potential that we know is possible.

But before we get to that, I do want to humblebrag on behalf of my team because they’ve worked so hard to get to where we are today and they deserve some serious recognition. Here are a few highlights over the past year:


Lesson #1: Invest in your people. They are your lifeblood.

Investing in your team is much more than free food, cool happy hours, and silicon valley perks. It’s about ensuring they see a path to empowerment and ultimately being able to make key decisions which will help them make a mark on the company and their careers. For employees and employers alike, the grass can often times seem greener elsewhere, but the same problems exist in almost every startup. So, instead of waiting to hire that next “rockstar VP” — invest in the manager or director that you have and signal to everyone in the company that you are willing to invest in the people that you have rather than looking outside the company.

It seems like everyone wants to be entrepreneur these days, so give your people the autonomy to create new opportunities internally and benefit in a commisurate way. This can be tricky if it takes you too off-course, but innovation should come from within and you’ll never make progress if you don’t allow room for some trial and error. For us, two times per year we hold full day “hack days” where the entire company groups into teams or 3 to 5 and spends a week working on any crazy idea they want. It fosters not only innovation, but also empowerment and creativity.

Lesson #2: Be Prepared to Falter…and Get Up Quickly When You Do

Last year, I spoke with another LA entrepreneur who said their 4th year was by far the toughest as they had exhausted all the “low-hanging fruit” in the business and getting traction was now much harder. The fact is that for most startups (and we’re no exception) things get harder, not easier as you attempt to continue growing at the same rate as previous years. Old customers / partnerships suddenly evaporate when a company goes out of business, new customers are harder to come by, and gaining traction in a new vertical can be just as tough as starting a new business from scratch. So, where does that leave you? It’s nothing new — startups are fucking hard. You develop a growth strategy, focus on executing against that and do nothing else until you’ve iterated to succeeding in that mission.

You are going to fail at some point. Things are not going to go as planned. You may even fall down — but don’t stay down. Sound the alarms, rally the troops, go back to doing what you do best and make shit happen — FAST. Find the root of what drives your business and focus on that maniacally until you breakthrough.

Lesson #3: Edit more than you write.

For founders like myself who are more operationally-minded than externally-minded, this lesson can be a make-it or break-it factor to getting to the company to the next level. At some point in your growth, it’s time to set the path, not create it. Or, to paraphrase Jack Dorsey, “…as a CEO you should be editing more than you are writing…” — otherwise you become the bottleneck to growth.

Hire the right people — mentor them, coach them, advise them — but stop trying to get into the weeds. Create process that helps them do their jobs better instead of trying to do their jobs for them. It won’t scale and they will resent you for it. When innovation and direction comes from within, everyone feels more bought in … it doesn’t mean you have to completely let go, just coach instead of do.

Lesson #4: Trust your gut, but don’t forget to listen.

As your startup gets bigger and has more success, your ego tends to grow along with it. Your strong decision-making is what got you here … but ignoring the input of those closest to you is a warning sign you’re going off the rails. Your employees, your advisors, your investors — you have to pick and choose when to listen and when to go your own way, but if you find yourself thinking your way is the right way 80%+ of the time….you’re probably in for a rude awakening.

As you get bigger, you’re getting further and further into uncharted territory. The risks become greater than ever before. Give real credence to those closest to you because they are seeing things from a different angle that you are likely blinded to. You often won’t know it until 6 months later, but do your best to take into account those that have been there before. It’s unlikely that you are the exception to the rule as you think you are.

Lesson #5: Find some balance in your life.

You’re 4 years into your startup. On average, startups take 7 to 10 years to exit….so, realize that this is a marathon and not a sprint. If you’ve made it this far (most startups die in the first 3 years) and you haven’t kept any semblance of balance in your personal life you’re probably exhausted and nearing burnout. A friend and fellow founder wrote about her path to balance here — which I think lays out the stake you eventually have to put in the ground.

For me, every year I schedule a couple of triathlons or half-marathons far enough in advance that I have to take time out to train. Being proactive about taking time off helps enforce it when it gets to crunch time. Remember, creating balance isn’t just good for you, it’s good for your team, your family, and ultimately your investors.

Finding balance will give you a different perspective and clarity around mission and vision breakthroughs. The only way to settle in for the long haul is to surround yourself with great people and focus on the areas you can make the biggest impact. And, everyone will thank you for it…

In Conclusion

While we may not be a fucking unicorn just yet, we’ve achieved quite a bit and I’m extremely grateful for that. Four years have flown by and I’ve made more mistakes than I ever thought possible, but I’ve learned some things along the way as well. For the 99.998% of you that aren’t on Uber’s growth trajectory — take heed and be prepared for bumps along the way. Take a moment to smile everyone once in awhile and pat yourself (and your team) on the back. You’ve done something amazing if you’ve made it this far.

Now…get back to work… ;)