My Year as a Tech Entrepreneur

When I was US Ambassador to Estonia, one of the best parts of the job was frequent contact with the country’s technology start-up community.

The founding of Skype in Estonia and its global success had spawned a start-up ecosystem that encouraged young entrepreneurs and attracted some of the smartest, most interesting people I’d ever met.

It was as different a work environment as I could imagine compared with the 30 years I spent with the State Department, and I found it fascinating. I was especially interested in seeing it from the inside and, when an opportunity to join a start-up arose almost immediately following my retirement, I grabbed it.

The start-up was Teleport, founded by two Skype alumns, Sten Tamkivi and Silver Keskküla, and initially aimed at helping digital nomads find their best opportunities, wherever in the world those might be. The slogan was “Free People Move” and I came aboard in a part-time position to help with user engagement.

Like the original opportunity, the end of the experience also came sooner than expected when Teleport was acquired recently by MOVE Guides, a larger firm in the same business space. Teleport provided me a great, accelerated view, taking me from start-up pains to exit in 13 months. Here’s what I learned.

It’s harder than it looks

As Ambassador, the Embassy’s economic officer and I would regularly meet with start-ups that were looking for advice, especially on issues involving the US market or business services. They might casually mention a “change of direction or product” which I now know means “finding something that people will actually pay for.” It’s harder than it looks.

During my year at Teleport, we grew from 35,000 to 260,000 users. The majority loved the platform, gave us great promotion scores and made frequent requests for new features — but were unlikely to ever pay for it. Finding that revenue stream while staying true to the founders’ vision for Teleport was the constant challenge.

Despite the number of Tesla’s driving around the Silicon Valley, the mythical great idea that quickly turns into a billion dollar unicorn is, well, mostly mythical. And it didn’t happen in my year — darn!

Working remotely is awesome

My commitment to Teleport was roughly 10–15 hours a week, working from home and on my own schedule. It was as great as it sounds. When you take 2–3 hours of work and spread it over 17 waking hours, it doesn’t feel like work at all. It also helps when you enjoy what you’re doing and see how hard the team is working.

Our one regularly scheduled video conference a week (ironically 8AM Monday morning California time — bummer!) was the only fixed time commitment. At the beginning I’d get up, get dressed and be at the computer by 7:45. Turns out, no one other than Sten turned the camera on. So why get dressed? A robe worked fine. I eventually stopped getting out of bed at all — just propped my laptop on a pillow and stayed under the covers.

I understand that a strong desire to work from bed is probably not the motivation-level most firms are looking for, but I can attest to its value. Team members worked where they wanted and when they wanted, but were fully productive.

It takes especially talented management to make this work and, fortunately, Teleport had that. As a company dedicated to remote work and workers, Teleport encouraged all of us to live the life. I traveled to Malaysia, Estonia, Washington DC, North Carolina and Los Angeles while still putting in my Teleport hours. Many on the team were doing the same. I recommend it highly!

Working with Estonians is even more awesome

With great respect for the Guatemalan, Norwegian and German members of the Teleport Team, working for/with Estonians was a highlight. As an American, and one who spent the majority of my career in US Embassies abroad, the American business culture was always the dominant environment.

While the Estonian business culture is a good fit for an American, it’s also a little different. I thought Americans were direct! The Estonians definitely have us beat — but in a good way. In my three years living there, I was struck by how little arrogance I encountered. It’s just not part of the culture, no matter how smart or how successful a person is.

Author with Sten Tamkivi — Teleport co-founder

Estonians are are also wildly funny (even in a second language) ridiculously well-informed and very forward looking. (Please forgive the gross generalizations — always necessary when talking about a whole country). As I have frequently said, the world needs more Estonians!

People on the internet are mean

As head of user engagement, I was the first to read most of the messages sent our way. While the majority of our users were terrific and appreciative of our efforts, there’s something about that “feedback” button that encourages certain personalities.

It had been awhile (never) since I’d received messages like “Hey fuck face, your app sucks and so do you,” or “Dickhead — thanks for the spam. Why don’t you kill yourself?” As I learned in diplomacy — never take it personally.

Communication philosophy

My biggest personal challenge was the difference in communication philosophy. I spent 30 years working in a classified environment, where “need-to-know” was the guiding rule. Moving to an environment where “everybody-knows-everything” did not come easy.

Inside Teleport, we used Fleep (a Slack competitor — but built in Estonia). All of our messages fed long conversation threads open to everyone — just keeping up with the conversations consumed a good chunk of my time.

It took some getting used to and I felt the founders’ patiently moving me to this style. I’d send an idea or thought to one of them or a team member and then see it shared in the appropriate chat with “Jeff had this idea….”

I was also the only guy starting each new message with a greeting. I understood that a thread was one continuing conversation, but it always felt rude jumping in without saying “hi” first. There’s also a different type of accountability with group communication — more ambiguity about who is responsible for what.

Analytics are everything

Teleport analyzed everything — daily traffic, time-on site, search preferences, blog performance, conversion rates, account deletions. Virtually no aspect of the operation escaped quantification.

I’m sure this is the norm in the data industry, but again, very different from my State Department experience. There, it was often difficult to measure impact and, if something wasn’t working, we would often just do it harder.

At Teleport, if something wasn’t working, we would try to do it differently. My team mates also consumed vast amounts of information, posting to chat threads dozens of articles every week on all facets of the technology world in addition to their own blog posts. Most days I felt smarter just knowing these guys.

Saying goodbye is always hard

I’ve been a member of some great teams. Teleport is definitely among them. Frequent departures, turnover and change are another part of the start-up experience. It was a great year. Thanks, Teleport!