Diego Bejarano Gerke of WiFi Tribe: 5 Things I Learned as a TwentySomething Founder

Saying ‘no’ to good ideas: I believe that most founders don’t say ‘no’ enough, and our lack of work-life experience makes us 20-something founders even worse at it. Why does it matter? Well, every time we say ‘no’ to something, we’re giving that thing that we said ‘yes’ to a better chance of surviving.

As a part of our series called “My Life as a TwentySomething Founder”, I had the pleasure of interviewing Diego Bejarano Gerke — founder and CEO of WiFi Tribe, a company that brings together entrepreneurs, freelance consultants, and remote professionals to co-live and co-work while traveling the world. He’s spent the last 4 years living in 23 different cities while building his company remotely. He’s a marketer by profession and a community designer by passion.

Thank you so much for doing this with us! What is your “backstory”?

I’ve been nomadic my whole life, and I now run a company that brings people together who want to live and work whilst traveling.

I don’t remember my past by years, phases, or things I did, but by countries. From the age of one, I moved with my family to a different country every couple of years. I don’t feel ‘at home’ in any one place. I’m half-German, half-Bolivian, but never lived in either of those countries. I speak five languages and spell-like a Brit, but for some reason, I sound American. Yes, I’m definitely a little culturally confused.

And since I started WiFi Tribe four years ago, I’ve been moving to a different city almost every month, living and working side-by-side with remote professionals from all corners of the world. These incredible people also happen to be… my customers.

How did I get here? By the end of 2015, at the age of 25, I was on my fourth failed startup. For 3 years straight, I had been hustling to make it as a founder, but I just wasn’t getting that breakthrough. What hurt more was that I felt I was wasting my youth. I wanted to travel while I had all this energy and freedom, and I wanted to spend more time connecting with equally excitable, passionate, and curious people.

So, I re-prioritized my life: I was going to fix the lifestyle part first and, only when I’d done that, come back to building a startup.

First, I got some freelance marketing gigs to sort myself out financially whilst keeping my freedom. Then, I sent an email to 100 friends inviting them to join me in Bolivia for a month. The idea was that we’d work remotely from there during the week and explore the country together on weekends. Finally, this lifestyle project needed a catchy name. Enter, WiFi Tribe.

It was never meant to be more than a break from the start-up grind. Ironically, it becomes the company I had been so desperately trying to build.

Can you share the funniest or most interesting story that happened to you since you started your company? What lessons or takeaways did you take out of that story?

I nearly killed WiFi Tribe just a few months after launch.

After our first successful co-living experience in Bolivia, we got a bit carried away. I thought that we were ready to double our size straight out the gate, so we launched two trips at the same time — one in Italy, and the other in Nicaragua. In our haste, we hired the wrong people, mismanaged our wire transfers, and failed to put contingency plans in place. And let me tell you: my shiny, confident, three-month-old business lost a lot of its luster when I had to borrow money from our paying members (a.k.a. our clients) to avoid everyone getting evicted from our house in Florence a few days after we arrived. The rent hadn’t arrived in our landlord’s account due to an error in the wiring instructions, and he wasn’t a patient man.

But we took away so many important lessons from that experience. We learned to slow down and move decisively but methodically, which is one of the reasons we’re still here when so many of our competitors are gone. We learned to hire slow and fire fast, and to always use our core values to make those decisions. And we learned that it’s nice to have a few extra Euros in your pocket so that you and your friends and customers don’t have to sleep outside on the streets of Florence.

What do you think makes your company stand out? Can you share a story?

This one’s easy, because our members tell us all the time: it’s our tight-knit community.

When we started in 2016, there was only one other organization offering month-long coliving trips for remote professionals. Then, in the space of a year, we saw about a hundred new brands popping up in this space, only to watch almost all of them disappear just as quickly. And the reason is simple: we figured out that what really mattered wasn’t the destination. It was the people. The community itself, the people who joined, were also the main value that we delivered to, well, the people who joined. (How meta!)

So, we doubled down on our people-first approach. We set up the most intensive interview process in our space, and followed a simple motto: we don’t sell, we select. We implemented a four-stage application process, including a personality test and an extensive one-on-one live interview with one of our team members, and decided to do the most counter-intuitive thing a growing business owner can do: we said ‘no’ to people who wanted to pay to join us.

But that was the right call. Within a year, our repeat rates went from 15% to 87%, and our first members have continued to travel with us, over and over again; some have done more than 15 month-long trips with us over the last few years.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

We have a very unusual relationship with our customers. So much so that it actually feels uncomfortable to call our members ‘customers’.

We’ve been living alongside our members for months at a time, spending most of our evenings and weekends exploring a new country together, and actually being a part of their own journey to success. These intense experiences we shared on a daily basis naturally led to forming incredibly close bonds.

Without knowing it, we had accidentally created the most incredible support network a growing startup could have. Talented people gravitated towards us and offered to help, firstly because of the bonds we’d formed, and secondly because they were so passionate about this being their community. This gave us access to resources we never could have accessed as a startup otherwise.

For example, when the company needed a bridge loan to be able to scale its operations, the community provided us a line of credit. This has allowed us to remain self-funded without any equity investment.

Or how about the biggest change in our marketing strategy? We’re now working with three brilliant Tribe members who are helping us transition away from paid ads and over to partnerships and organic content marketing. These are some of the sharpest marketing minds in the world — the kind of talent that is almost impossible to access when you have very little to offer.

The lesson? Take care of the people who matter — your customers — and there’s a good chance they’ll take care of you in return.

Are you working on any exciting projects now?

As a matter of fact, yes — we’re about to launch our two biggest and most exciting projects to date!

The Remote Agency Incubator: we’re partnering with remote business specialists Beyond The Office to offer a specialized business incubator in Brazil this May to help freelancers and other remote workers grow their businesses.

Remote in 60 Days — a $10,000 Travel + Business Scholarship: And in March we’re launching Remote in 60 Days, a $10,0000 scholarship to help freelancers and agency owners build a business that takes less time to run and earns them more money. In fact, one scholarship recipient will secure a free spot in our incubator in Brazil, and then another free month with us in Peru — flights included!

We’re excited about being able to help so many young entrepreneurial people take the next step upwards in their remote working careers.

How have you used your success to bring goodness to the world?

We’re very fortunate that our members’ happiness is directly correlated with our success. We conceived of WiFi Tribe as a way to meet a group of friends that are able to work remotely and who choose to live out their freedom by traveling the world together, but somewhere along the way, we realized that we had unlocked something even more meaningful. Members started telling us that they had found deeper, more authentic connections with other members of our community than with their own communities back home. Now we understand that our community isn’t just a temporary replacement for home — for many, it’s becoming a place where they finally feel like they belong.

Do you have a favorite book that made a deep impact on your life? Can you share a story?

Delivering Happiness by Tony Hsieh. It’s a great read, with a captivating story that ends in a few powerful messages for entrepreneurs. What resonated the most with me was the importance of getting the culture right.

At WiFi Tribe, values and culture literally have double the importance: Once for the team, and then again for our community. From day one, we set the values for our community. More importantly, our values are the foundation of our recruitment process; anyone who applies is assessed with our values in mind to determine if they’d fit into our unique culture.

But it wasn’t all rosy. We also made big mistakes when hiring for the team. In our first years, we chose several talented people who were able to add value immediately, but we didn’t put enough effort into getting the value-fit right. Unfortunately, these hires never worked out well in the long-term. We had to let several people go and accept that we’d lost a lot of money in the process.

Can you share 5 of the most difficult and most rewarding parts of being a “TwentySomething founder”. Please share an example or story for each

1. Big dreams, but no leverage: We’re just getting our professional lives into gear, and make the rather unreasonable decision to start a company. We start off with lots of confidence, but not too much to back it up; no credibility from past successes, a meager pool of capital, and a limited network. But when we make something out of nothing, whatever it is, now that feels rewarding.

I still believe in my last failed startup, but I now know that I didn’t have enough leverage to make it happen. I was working on an invite-only community that would connect high-profile, successful founders to each other around the world. In-person meetups were going to be facilitated through an app. However, I didn’t have the capital to invest in a tech team to build the app, no professional network of high-profile founders to launch to, and zero credibility.

2. Living for today vs. tomorrow: Building a startup is all about living for tomorrow. Every day we show up because we tell ourselves that we’re working hard to make our future really awesome. We’re sacrificing our today for a better tomorrow. What frustrated me about this mindset is that by living this way, we actually let one of the best chapters of our life pass us by — the part where we’re young, curious, excitable and full of energy. Life happens in stages — if you miss one, you can’t go back. Sure, you may have the money someday to do what you really wanted when you were young, but will you still want to? Probably not. That ship has sailed.

I believe that a good life is about enjoying every stage of it, without losing sight of what you need to do today so that you can enjoy the next stage just as much. That’s how you live without deathbed regrets.

I wanted to travel while I was young, and at the same time learn as much as I could from people who inspire me. That’s exactly what I got from building WiFi Tribe, and to this day, four years later, I still permanently travel with our community of remote professionals.

3. Saying ‘no’ to good ideas: I believe that most founders don’t say ‘no’ enough, and our lack of work-life experience makes us 20-something founders even worse at it. Why does it matter? Well, every time we say ‘no’ to something, we’re giving that thing that we said ‘yes’ to a better chance of surviving. Our first startups need all our attention and energy. So many cool ideas will come up, but it’s your job as a founder and CEO to say ‘yes’ to a handful of things that really drive your business forward, and confidently say ‘no’ to the rest.

Every month, I co-live and co-work with 15–25 entrepreneurs, freelance consultants, and remote professionals. You can imagine just how many ideas for new products, services, or side projects come up. But in a year, I’ll say ‘yes’ to one or two brilliant ideas and ‘no’ to a hundred good ones.

4. Being true to you: About half-way through my time at university in the UK, the startup craze hit. And it hit hard. Suddenly, everyone wanted to become a founder and entrepreneurship was taking over the traditional career aspirations of climbing the corporate ladder. I was definitely hit by that craze too. For three years, I desperately tried to become a ‘successful founder’ of a scalable tech startup. I was lucky that WiFi Tribe finally worked out, but I could have just as well ended up frustrated, disillusioned, and with my confidence shattered if I hadn’t gotten lucky when I did. So many of my friends who wanted to build companies had to experience this as well, and some of them are still stuck in that limbo today, struggling to make it and unwilling to move on with an alternative career path.

While I appreciate that the big startup hype was inspirational, I worry that too many of us end up worse off than we would have otherwise been because we’re living out the life that the media prescribed to us.

5. Tons of passion, zero wisdom: We’ve got all the energy, but no patience. And, we don’t know what we don’t know. That makes us prone to making big mistakes; running very fast, with lots of conviction in the wrong direction. Building a business will always involve taking risks, but they should be calculated risks. And the ability to calculate only comes from experience. Every time we put a new destination on the calendar and book a property, we’re taking a gamble — can we fill that property, or will we lose the money we’ve locked into it? In the early years, that gamble was riskier than it is now because we had nothing but passion and excitement guiding us. But over time, with a bit of experience under our belt, we’ve learned to make smarter decisions based on what we know, rather than having to rely on what we feel.

What are the main takeaways that you would advise a twenty-year-old who is looking to found a business?

Train your “idea brain”: You can train anything and become better at it. If you haven’t found that brilliant business idea yet, you can get better at that too. Set aside 15 minutes a day to brainstorm business ideas. Don’t do anything else at that time. Show up every day.

Some days, you’ll have tons of ideas, and on other days, you’ll draw a blank. It doesn’t matter. The point is not to find the actual idea — the point is to become good at thinking up ideas. And yes, as a side product, you’ll eventually hit on something that fills you with excitement. But more importantly, you’ll become good at ideation, and that’s a skill you want to hone for life as a founder.

Don’t build a startup… yet: Join a startup before you build a startup. Think of it as your free startup university. You get to learn from someone else’s mistakes, understand how to deal with startup risks, learn about different management styles (the good, the bad, and the ugly), develop a strong work ethic, and see what it means to hire right, and how much it sucks when you get it wrong.

Making some of these mistakes on your own business can cost you a lot of time, money, and probably (statistically speaking) the failure of your business. Wouldn’t it be smarter to just avoid these mistakes in the first place? If you choose your startup job wisely, you can also use the opportunity to get really good at a skill you know you want to deliver to your own startup in the future, and deeply understand an industry that you might want to plug your future startup into. Most importantly, absorb EVERYTHING. Be hungry.

Start a side-hustle: When you have a stable income, that’s the perfect time to start experimenting. You can work on ideas without the stress of not being able to make ends meet, which frankly dumbs you down. Carve out a few hours every day to start working on passion projects or side-hustles. Here is where you’ll apply what you’re learning, hone your skills, and hopefully (after lots of iterations and failed mini-projects) you’ll hit on something that works. And when you’ve got something that actually makes money, that’s when it’s time to quit your job and go, full-time founder.

Start lean: I started my first four startup projects with an elaborate corporate structure, a 30-page business plan, a company org chart, a hefty founder agreement, and a lofty vision and mission statement. All four failed. I started WiFi Tribe with a Squarespace website and an amateur email to 100 friends. That one succeeded. This time, we decided to start lean and deliver value before dealing with all the unnecessary fluff that didn’t get us anywhere before. You can always go back and fix all of that as soon as you’ve got something tangible that works and actually make money. Save yourself all the formal business foundation nonsense that’s not necessary when you don’t even know if your business is a… business.

Think… small: I believe the startup world would be a much better, much happier place if more young founders subscribed to this. The media has hyped us up to start world-changing tech companies out of garages with ping-pong tables and bean bags before we’re out of school so that we can humble-brag that we dropped out of education to build our first business. And not just that, the media would also like us to scale that garage startup into a massive tech enterprise by the age of 25, to later go IPO at 27.

The reality is that we really don’t know very much about anything when we start a business in our early 20’s. I firmly believe that the best thing first-time founders can do is to start building a business for the sake of learning how to start, build, and scale a business. The most important business principles work the same for every business, whether a trailblazing tech company or classic brick-and-mortar business; how to spot talent, how to hire and train, creating processes, managing finances, delegating, etc. Set up a smaller business with a more predictable business model as your sandbox — here, you will play and learn until you’ve understood how the world of business works. Then, you can go off to making better mistakes on your next venture, instead of failing right at the basics.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this. :-)

I would love to get the chance to have breakfast and a good coffee with Tony Hsieh. He’s given me the most important mindset for the long-term success of a company: nailing the company culture.

What is the best way our readers can follow you on social media?

You can find WiFi Tribe on Instagram — https://instagram.com/wifitribe.co, or Facebook — https://facebook.com/wifitribe

This was very inspiring. Thank you so much for joining us!