Success can be more stressful than failure
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My second startup, Omnivore.io, came primed for success. I had previously been the customer facing representative at SubtleData where I drove customer’s integrations with our API. So when I launched Omnivore as a replacement in the demise of Subtledata, we had dozens of clients screaming for our product.
Even more, we had big companies calling us up. I can’t say who but I visited with some big, every day Silicon Valley companies and their executives. Specifically those dabbling in Fintech and maybe a FAANG or two.
Within weeks of our product becoming ready for prime time, I experienced something I really had never encountered before. Rather than stressing about the failure of my business, I was being stressed out by its success.
It’s different in many ways. Instead of having a lot of time to think about why you are failing, you have zero time. Everyone needs you. Your time is suddenly not only in very short supply but your most precious commodity since there are only so many hours in a day and while we founders would like to think not, we do need sleep, rest, and time away from work else we’ll burn out like I, sadly, rather quickly did.
The first lesson I failed to learn which I will tell you to learn quickly is to delegate delegate delegate. Give away as many of your responsibilities as humanly possible. And don’t let them come back to you with questions. You have to fully enable them to direct teams and make decisions autonomously. You give a direction you want the company to go in, and you need to hire someone you can trust to understand your vision, execute on it, and have the company arrive, on time, exactly where you want it to be with as little input from you as possible.
Your only job in a successful startup is to generate EV. Any activity that is not generating EV is not your responsibility anymore. Give it to someone else. Ideally, any responsibility not maximizing the EV you could be generating is not your job either.
For the most part, that means you are in charge of sales, BD, and investor relations. Those are where time investment pays off the most in a startup.
This is where it starts to get interesting because what if you don’t have enough time to manage all of those, but they still require the CEO’s attention? This is the situation I found myself in. This is where things that seem like luxuries to normal people become cost-efficient to corporate executives.
Not many people realize that the reason corporate executives fly private is not for luxury, but to save time and so they can work in peace during the flight. That’s because they generate more value in the air than the cost of the flight. It’s a sound investment.
Similarly, I found myself going to 4-6 meetings around SF a day. Waiting for Ubers was eating up a costly amount of time. Similarly, doing errands and simple things like keeping my food stocked was costing the company a lot of money since I was not working.
So, we got me a private driver and personal assistant. It was nothing fancy per se. Just a Lexus ES that I never had to wait for with a laptop in the back seat. When he wasn’t working, he did all my errands, made sure my house had fresh food and the fridge was stocked, etc.. We dd the math and he paid for himself in the first 5 days of every month, especially not having to ever wait for a car and being able to work in the backseat in downtown SF traffic on my way to and from meetings.
It wasn’t about luxury, it was good time management and a good investment by the company. The fact that it made me feel like a million bucks was a great side effect that also probably gave me the confidence to seal a few deals.
The greatest perk was one we didn't even have to pay for though and was a lesson in time management a customer gave me. We were working with a large payment processor in San Jose. Every week, since it was the fastest way, I’d take the Caltrain down for a meeting with either their executives or their integration team. They were very close to the Caltrain station so the 2 minute Uber ride in San Jose was a non-issue.
Within a few months, it became apparent this was not going to work anymore. It was basically 3 hours spent traveling with spotty cell service so I couldn’t work and despite the potential size of the contract, it was just too much wasted time.
So I reached out to the highest exec contact there and told him that the travel time was just too much. I felt very dejected. Although, without skipping a beat, he just responded:
“Oh, we’ll just send a helicopter”
Um, what?
So every week, they chartered a helicopter from the Oakland airport, which was about a nine minute ride on average from my office in the financial district for a 20 minute ride to San Jose to a waiting car for a 2 minute ride to their offices, and then back again.
The best part was the helicopter had WiFi so I actually don’t recall ever looking out the window and would work the whole way and back despite what I assume were beautiful views of the bay and peninsula.
Again, it wasn’t even a fancy helicopter. It was loud and uncomfortable. It was just a way to get me from point A to point B as quickly as possible so we could do business and make money.
Despite all of this, I never learned to take care of or time for myself and while I built a fast growing company, I burnt out, made my employees feel upset since I never learned to trust them by delegating anything, and ended up leaving rather early in the process. The company went on to be a wild success on the back of the technology I originally built for it and the groundwork I laid, but I’m sometimes ashamed I didn’t learn to better manage my time or let go of this overwhelming feeling of needing to control every aspect of it. It’s very hard as a perfectionist to let go and trust that someone will get the job done right. I’ve since learned my lesson, but it’s still very hard when an employee doesn’t get something right to not fall back into old habits. Although I’m sure I am also to blame in most of those circumstances.
So today, I face a similar situation. My new company, Sibble & Associates, has found a niche that is seemingly not just underserved, but not served at all. We’re all quite astonished. Our potential customers are very happy with the product we’ve put before them and demand seems to be skyrocketing by the day. Just in the past week, we’ve gone from wondering if we can sell it to how the fuck are we gonna scale fast enough? And once again, my time is becoming a primary constraint.
This being my 3rd rodeo, I know what to do. I currently do the accounting. Talking to a firm tomorrow. Separating myself from any sales and marketing I don’t 100% have to be a part of. Identified 3 employees today we want to bring on that will take over the majority of the actual client work I am currently doing so I can focus on building the business and growing our client base and revenue. Talked to all 3 and they are ready to get hired at a moment’s notice. Contacted 5 investors so we can get a cash cushion if necessary if we need to scale up before revenue arrives.
I can say two things. I’ve never been so happy and I’ve never been so tired.
And as any entrepreneur can tell you, or at least the ones who understand this:
It isn’t the millions of ARR staring me in the face that make me happy. It’s how much goddamn fucking fun I’m having.
There’s nothing in the world like building a company, especially when you own 100% of it and have no investors to report to like slaveowners. I’m working 12-14 hour days and loving every minute of it. And this time, I’m being more careful and plan to be in it the long haul.
Sibble & Associates provide technical due diligence services to VC firms as well as angel investors and offers the ability to build prototypes, MVP's, and provide fractional CTO services to startups, all under one roof, ensuring that our clients have the ability to bring their technical concepts to fruition.