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Reflecting on 3-Years as a Startup Founder: Strength, Persistence and Fear

About 3 years ago (2010), I made a decision to quit my hedge fund job and start upon a journey to build my own company: Tout. This blog entry reflects on the past three years and gives you an update on where I stand today.

2010

By the end of 2010, I had already quit my job. Shipped 2 products. Launched a Services business with clients. Now what!?.

As 2010 came to an end, Tout the most promising of the ideas I had been working on had acquired nearly a thousand users and even started generating revenues from day 2 of launching. Seems tiny in retrospect but for back then it was amazing. All I really had was a glimmer of an idea and a bit of market validation.

At that time, it was still just me. I was the Founder, Engineer, Designer, Marketer and Customer Support. But, beyond just me, others took a look and could tell there was something there. It was quite a bit of a contrarian view at the time. Instead of betting against email and trying to make everything “social”, even then, Tout was about making Email work better and believing that Email/Digital 1-to-1 communications would grow in usage and the tools we use to communicate would need to evolve.

2011

In 2011, I decided to drop everything else and concentrate all of my efforts on building Tout as a real company.

With the rise of convertible notes, accelerator programs and the general fundraising climate of 2011, I decided to switch from a bootstrapped startup and raise money for Tout.

Through 2011, I joined the 500 Startups Accelerator Program, built out a team of some seriously amazing people, Raised a seed round of nearly $800k from the likes of Esther Dyson, Eric Ries, Dave McClure and others, and built out ToutApp to what I like to call “Version 1.0”

Although I had made it a tradition to write a “Year In Review” post since 2009 or so, I ended up not writing one at the end of 2011. I had done so much, Tout had grown so much, and yet I felt no sense of finality as December rolled around.

2011 was Tout’s Foundational Year

Through the course of 2011, we grew our user base, we grew the footprint of our product, we grew our revenues. We talked to customers and got a core understanding of the problems we were solving. Looking back, it was a foundational year that every startup with a long enough view needs to have and needs to go through. However, as the end of 2011 rolled around, things didn’t feel all that great.

After spending the summer in California, it became evident that I needed to stay there instead of going back to New York to maximize the outcomes around the business. However, with a distributed team stemming from New York, Indiana and California, merging everyone into one place would be downright impossible.

Tout was my baby. Moving to California felt like a no-brainer to me. Fortunately, my wife was incredibly supportive as well and didn’t give moving a second thought either. However, it wasn’t the same case for the rest of the team. They weren’t founders. They had families, friends, lives that they couldn’t necessarily uproot. And so, Tout came back to being just me.

As the end of 2011 rolled around, we did a holiday promotion called “Your 2011 Email Year In Review.” Through the course of the holidays, we signed on 20,000 users, and got featured on The New York Times, Mashable, TechCrunch, and countless other publications. The servers crashed and burned, but somehow we got through it. We acquired users, converted to revenue and got our name out there.

No one knew it was all being done by a now-1-person company. Not even the New York Times.

It was a serious conundrum that even I couldn’t believe. As our transition to San Francisco brought down our actual team count to 1, our user base continued to grow. Our revenues continued to grow. And since I was already used to being the one-man-show, the product continued to get better.

2012 – Tout Grows Up

So as 2011 ended, I stayed calm and carried on; however, I couldn’t find the mindset to write down a “Reflecting on 2011” blog post because of the utter lack of finality or at least one worth writing about.

As 2012 started, it became clearer than ever that Tout was onto something important. Even if my faith or my beliefs faltered for as second, our amazing customers and community constantly reminded us how Tout made a serious impact on their day to day which they would more than happily pay $30/month for. And so while in retrospect January was probably an insane month for me, at the time I felt like a surgeon standing in front of a dying patient with steady hands and a plan on what needed to be done.

As January rolled into February and onward through Q1 of 2012, we closed the remainder of our seed round with Founder Collective and a few others. What we needed to build for Tout to take the business to the next level was clear, and so I continued to set out to establish ourselves in San Francisco and make key hires in Support, Engineering, Sales and Marketing as we continued to grow our paid customer base.

As I look back at 2012, I can wholeheartedly say that its been the most intense, most stressful, most amazing, most balanced year of my life that I have ever lived. In other words, it has been the quintessential definition of an Entrepreneurs life at its extreme.

2012’s Focus Was on Product

Through the course of 2012, we’ve achieved what we call “full coverage” here at Tout meaning, we’re now fully and deeply integrated into Gmail, Outlook, Salesforce, iPhone, and all major web browsers. We’ve developed our on boarding, training, support, sales and marketing programs and we’ve figured out ways to predictively convert new customers to paying customers to retained customers in a systematic way.

We completely rebuilt Tout’s GUI from the ground up and expanded the platform well beyond simple Email Templates which is how Tout got its start back in 2010.

And most importantly, while I always referred to Tout as “we” even when it was just me, through 2012 we grew Tout’s team to make sure all key areas of our business including Engineering, Customer Happiness, Training, Marketing and Sales had smart individuals to think through a design and operate it like a well oiled and beautiful machine.

Don’t get me wrong. We’re still tiny, there’s only 6 of us. However, the ratios around the business and the amount we get done with just 6 people, never cease to astound me. As 2012 comes to an end, we have more computer screens than we have employees. We are integrated into more platforms than we have employees. While most SaaS companies enjoy < 1% of their user base as paying users, we have nearly 3% of our user base paying us for our B2B offering. And of course there’s my favorite, nearly 8% of users signing up every week will end up paying us with their credit card.

2012 – I Grew Up as a Startup CEO

While the end-state of 2012 feel a heck of a lot better than 2011, I’d be doing all of you a disservice if I wasn’t honest about exactly how hard, tiring and painful this year has been. There is absolutely nothing of certainty when you’re doing a startup. And for the better part of this year, I’ve slept very little at night because of that.

When you’re just starting out, like I was back in 2010 and through a good part of 2011, you have absolutely nothing. Having absolutely nothing is one of the best blessings one could ironically ask for. Having absolutely nothing means you’ve no reason to fear anything because you’ve got nothing to lose. The smart ones through this period go through a period of amazing wonderment trying different things, taking bigger and bigger risks, and doing anything and everything possible to make something to replace the nothing.

Once things start to click. Once that first big customers comes on. Once that really great investor comes on board. Once you win that really great deal it all changes. Its the dream of every startup founder, some call it product market fit, some warn of it as “be careful what you wish for.” Once you have something its a whole different game you start to play. Once you have something its no longer about doing anything and everything and seeing what sticks, it becomes a careful game of management.

Management is a term we think we understand, but until you really stop and think deeply about it, especially as a Startup CEO you don’t truly understand the breadth and weight of the responsibility.

2012 – On Not Sleeping At Night

As 2012 came to be and things started to progress with our product, our market, and our team, I entered into a mental state for the majority of this year that I believe has no real name or categorization but can only be attributed to serving in the role of Startup CEO.

The first thing that happens in this state is related to sleep. Sleep becomes redefined. It’s no longer “go to bed because you can call it a day” it’s more of a “well I guess now is the time to sleep but all you can do is lay awake and stare while your mind processes thinks and reevaluates scenarios at light speed.”

You start to incessantly check Twitter/LinkedIN/FB in the morning only to confirm that the darlings of Silicon Valley are still indeed killing it and you get another fire lit under you just so you can try and “catch up” today.

God forbid you do get featured profiled or become the darling now you work 10x harder than your already 100x pace because behind the scenes things still feel like you’re running an ugly dirty sausage factory.

Although you conceptually realize that this job is all about keeping your head in check you still struggle to deal with the raw emotions of it all.

2012, I Know Why We Work So Many Hours

The interesting thing is the emotions rarely come into play during office hours. Between the hours of 9 and 7 (on average) when I was actually in the office, it was like being in a symphony orchestra. You focus on the most important things, you code, you talk, you brainstorm, you fix problems, you DO things because then at least you feel like you’re doing something about the fear of failure you’re doing what you need to so you can carry things forward to the next level.

Maybe this is why we work so many hours. Not because we are so damn productive at our 80th hour of the week, its more because not working is just so damn unbearable.

Speaking of non-work-hours. At some point you probably signed up for a real life with real friends and real relationships. Through 2012, I had to either make a conscious decision to cut off those ties and make my company my life or decide to pursue that elusive “work-life” balance.

Fuck work life balance. You never actually achieve balance because you can’t stop thinking about it. But – you still go to the birthday parties, double dates, you drive your house guests to napa and you spend Sunday afternoons grocery shopping.

You talk you laugh but inevitable you get a little quiet. A little reserved. Truth is you’re just going through the motions. You’re not really there. You’re numb.

Inevitably they’ll ask how’s the company you put on your PR face and give the byte sized clips. Worst case – you say “great!” Even worse, they happen to mention the name of a competitor. Thats it. You can now clear out the rest of your night schedule at that point and sign yourself up for at least one more restless night.

2012, Mondays, Days, The Concept of a “Day”

And so when Monday rolls around you’re just exhausted from trying to be normal and escape numbness but now that Monday is here all you really want is a day alone where you can just hear yourself think. But that’s out the window because there’s a slew of customers, employees, investors etc roaring to go needing things doing things and so you just jump in.

Thats fine though, give it 10 minutes into the office, and then you’re back into the symphony orchestra again. It doesn’t matter how tired you are. You don’t even remember it anymore at this point. You’re in the zone. You love it.

At the end of your day your loving wife might ask you how your day went. She cares. She deeply cares and she wants to relate. Except to you it doesn’t feel like a “Day” it feels like you started your day last Thursday and haven’t skipped a beat and you’re already planning tomorrow and tinkling about next week and so your exhausted overworked mind literally has no synthesis on how TODAY went because for all practical purposes there is no today and no tomorrow there is just ON and OFF and you haven’t turned if OFF for god knows how long and you won’t till you reach your goal.

None of these things are good or bad. This is no ones fault except your own. Its my own fault. I signed up for this. Remember? I quit that 6 figure job so I could have this instead.

2012 – Goals

Goals. Thats a funny word in this stage of the company. We have milestones, weekly goals and you hit them or you were aggressive in goal setting and maybe you don’t. In the back of your mind though, you know very well that all of this is arbitrary. The only goal there really is the only one that really matters is when you’re “wildly successful.”

By now you’ll have forgotten how many times you pushed back that goal post. You won the little battles and you just kept pushing forward because every win felt like a small win and you felt like there was always something more and so you forged ahead because that’s the right thing to do and so at this point what is the goal really? Wild success. Killing it. IPO. Acquisition. Surviving.

I’m Still Loving This

From a well paying desk job to nothing to something to now. Today, Tout stands strong as the most complete Sales Communications Platform. Through 2012, we’ve come together as a seriously amazing and fun team, we’ve brought on customers that are using our platform to do amazing things, and I can’t help but shed a tear when I watch this year-end video we put together featuring the state of Tout and the team.

2013

We’ve worked hard over the past 3 years and now we have a platform that is unparalleled. We’re switching from being inward and purely customer focused to expand into aggressive Sales and Marketing. This ain’t vaporware, this is a real throughly tested and deeply thought through solution now. We’re all seriously excited about making sure every Sales Team uses ToutApp.

Yes its hard. But this is Startup life.

Email me your thoughts: tk at toutapp dot com.