Scale yourself: 12 techniques to learn and grow as a startup founder
Read about the methods I used for learning and personal growth on my startup journey from 0 to 300 employees and a successful exit under the age of 30
Back in 2012, I was walking on a sandy path next to Hamburg’s Elbe River when something suddenly clicked in my head. For the previous three years I had been building up the German marketing company RegioHelden, which I started as a solo-founder right out of university. I had scaled the company to 25 employees, had raised the first million in VC, and revenues were growing. But I was struggling in my role as CEO. Having had no actual work experience before starting the company I just worked my ass off and tried to solve every problem by myself. I felt that I wasn’t doing my organization a favour because some employees had quit — the reason being a “lack of leadership”. I felt burned out, unhealthy and unhappy in my role as CEO.
What made it click in my head was a comment made by a very experienced entrepreneur, who was walking alongside me that day. Having exited his previous company he was now building a new venture with its headquarters in Berlin. His home was in Hamburg, 2 hours away. His comment was basically this:
“I manage the company one day a week. What I owe my investors is a successful business, not time spent in the office. Therefore, I hold all my meetings with my direct reports on Mondays and then leave the office for the rest of the week.”
Of course, my goal was not to reduce my working time by 80%, but rather to restructure my CEO role. But the comment made me ponder about my role in the weeks that followed. It ultimately led me to push much more responsibility to the rest of the organization. In the months after this conversation, I started to focus my time and energy on my strengths and things I enjoyed (both correlated greatly with one another!).
Without this reflection and subtle change in my role, I doubt that I would have been able to scale the company to over 300 people, build up a great, self-reliant management team and have sold it in an eight-figure deal 3 years later. I learned a lot on that beautiful day in Hamburg ☀️
The 12 learning techniques for startup founders
By definition you can’t really prepare well for being a first-time founder. You learn entrepreneurship by doing it. And if you’re not constantly learning your company will outgrow you.
“You learn entrepreneurship by doing it.”
To get you started on your journey of a lifetime of learning, I have put together 12(+1) techniques that helped me learn and grow in my 10+ year journey from being a twenty-something first-time founder to building a company of 300 employees, closing more than 15 VC deals, multiple M&A projects and developing into my current role as an investor.
General learning techniques
1. Before you start, learn how to learn
Before actually learning new things, it might be helpful to think your learning strategy in order to become more efficient and to save time.
What’s your learning style? Do you mostly learn by reading, listening or doing? I personally learn the most by reading, summarizing and teaching the content to others (guess why I write here on Medium 😉). I also try to collect important learnings in lists and mindmaps that I go through on a monthly basis (in asana or MindMeister). It’s astonishing to see how much I forget from month to month.
Invest a little time and think about how you learn the most productively. It will pay off. This coursera course might also help: Learning how to learn by Barbara Oakley.
2. Invest in practice (like the athlete you are!)
A professional athlete spends more than 90% of their time practicing and maybe 10% in actual competitions.
I would say in terms of pressure, performance, stress and the need for adapting, being a startup founder is comparable to being a professional athlete. But how much do you practice as a founder? For me, it was 100% “competition” and 0% “practice”/learning at the beginning.
Over time, I shifted to spend around 10% of my time (~6–8h/week) on learning activities. You will realize that the techniques I offer in this article take time. When I look back, I would say that those hours were the best investment I ever made because it massively improved the other 90% of the “competition” time.
3. Find out what to learn and create knowledge map
I went through my first years as a founder and picked up random things. For example, I heard someone speak about company culture at a conference and learned a little. Then I went to a leadership seminar. The next day, I would read an article about KPIs. You get the point... This kind of “random learning” is valuable but slow-moving.
It might pay off to create some kind of “knowledge map” about what you already know, what you don’t know, and especially what you should know at your current stage.
“It might pay off to create a knowledge map”.
For example, it makes sense to actively learn about people management when you hire the first employees. Not years before and hopefully not a long time after.
When I realized that I would need to do several funding rounds I started to attend seminars and read books on business negotiations, which helped me a lot later on.
When you are putting together your learning agenda, think about the right timing, the stage that your company is at, and the current/future bottlenecks.
Learn from other founders
A lot of the things I implemented in my companies came from other founders who had been in similar situations (just like my friend in Hamburg). Remember that the solution to your problems is almost always nestled in someone else’s brain.
4. Talk to other founders
As a startup founder it’s lonely at the top. Your school friends probably don’t “get” the difficulties you face. Your spouse, who’s probably not an entrepreneur themselves, may not get it neither. The solution? Talk to other founders about your challenges. They might have already found a solution. After all, 99% of your problems are not unique to you (although it feels like it!) and have been solved by others before.
“It’s lonely at the top.”
— every first-time founder
Why not host or attend a founders’ meet-up? Why not hold a monthly founders’ dinner or host a breakfast event in your city if there isn’t one already? Why not contact other founders from your university/school and talk to them?
5. Join the Entrepreneurs’ Organization (trust me on this one)
I can’t stress enough how much I knowledge I gained from members of the Entrepreneurs’ Organization and how much of said knowledge I implemented in my companies. Joining EO was truly one of the best decisions I have made in my life.
The Entrepreneurs’ Organization connects you with fellow entrepreneurs in your area. You meet in small groups of 8–10 people for very structured meetings to discuss challenges once a month. For my first 5 years in the organization I flew 600km (I think that’s around a million miles 😉) all over Germany to attend the meetings every month. Totally worth it.
There are more than 15,000 members of EO worldwide, organized into hundreds local chapters. To qualify to apply, your company must make more than 1 million USD in annual revenue. If you’re below that but over 250,000 USD, you can apply for the EO Accelerator Program. Trust me, you won’t regret it.
(If there is no local chapter in your area, reach out to me and I’ll tell you how to create one.)
6. Travel with other founders to learn and have fun
I traveled to conferences like SXSW and PubCon with groups of entrepreneurs. Traveling and spending time together creates a certain amount of trust. Trust enables deep conversations about actual problems and solutions (instead of the usual “How’s your business”, “Great!!”). Don’t go to hotels when you travel together. Rent an apartment on Airbnb with a big-ass living room. It pays off.
A couple of years ago I started to attend at least two annual “founder retreats” with 6–8 close friends of mine, who are also entrepreneurs. We have an amazing time together and learn a lot from each other. That’s also the reason why I started Digital Founders Camp.
Shape your thinking with mentors, coaches and industry experts
Behind every professional athlete, there is an exceptional coach. In entrepreneurship it’s so easy to get lost in the day-to-day activities so that an external perspective on things can be invaluable.
7. Get a mentor that suits you and the stage your company is at
In the second or third year I was talking to my mentor Peter about a new video projector we had bought for the office. His question was “How much did it cost?”. I replied with the price. Then I realized that it was a trick question. His answer was, “If you know exactly what the fucking projector costs you should think about your priorities. Are you a CEO or an office manager?”. I always loved Peter’s style of communicating 😉
A mentor is someone who is usually older than you, has gathered relevant experience, and is willing to share that experience with you on a regular basis. When I started RegioHelden, my mentor Peter and I would talk several times per day because my desk was in his office. That was the perfect setting for me. Those regular 5 to 10-minute talks proved to be invaluable because I could not only pick Peter’s brain, but he also challenged my thinking and my decision-making. We could talk about big things like strategy and small things like, well... video projectors and my priorities.
What should you look for in a mentor? Relevant experience, networks, and trust. I think the most important aspect in the relationship is the trust between the two of you. You have to be able to tell your mentor everything that’s on your mind. Yes, even that you’re burned out and want to quit. A good mentor can probably help you in that situation.
How do you find a good mentor? I met Peter through a mutual friend (a lawyer). Think about older entrepreneurs in your network. Ask the people you know. Go to business events and approach people there. Try cold-emailing your ideal mentor nicely(!) and invite them for lunch. Please don’t think that a mentoring relationship can develop overnight. Good mentors usually have a lot on their plates and don’t wait for you to show up. Maybe they don’t even consider themselves to be mentors. Think about what you can do for them. Let them invest in your company? Connect them with relevant people they can benefit from? Share your knowledge and help them with specific problems?
What’s in it for the mentor? I have never paid a mentor, but usually let them invest in my companies at discounted rates and/or gave them virtual shares. Also I shared insights from my company that might have helped them with their other projects.
One last thing about mentors: Always think about the stage your company is currently in and what it needs. Over the years at RegioHelden, I had 3–4 different mentors because the knowledge I needed changed over time. For example, Peter had a very broad and general knowledge about entrepreneurship and company culture, but not necessarily about building a nationwide sales organization. So when it came to building such an organization I searched for a mentor in that specific field.
8. Get a business coach to help you reflect
Coaches helped me with my own reflection process by asking good questions. I used regular business coaches, psychologists, sports coaches and even a hypnotherapist for mindset coaching (highly recommended!).
The difference between a coach and a mentor is that a coach doesn’t have to know much about your business or industry but rather has to be very good at asking questions and helping you reflect. I paid my coaches hourly rates of 150–300 USD and would work with them over different time spans ranging from just a few sessions to longer stretches of a couple of months/years.
Learn from other people
Of course, a lot of things you’ll need to learn are specific to your industry/stage/region. So only talking to other founders, mentors, and coaches won’t necessarily solve all of your problems.
9. Host specific events/meet-ups
You don’t know a lot about “Amazon SEO” but need it in your business? Why not host a meet-up and maybe invite an experienced speaker? Oftentimes it will cost you close to nothing (🍕 & 🍺) and can create a lot of value for you and the attendees. Plus, you don’t need to know a lot about the topic yourself if you invite an expert to hold a talk.
If you’re a little further, you can also have your employees host their own meet-ups. I think the “Stuttgart WordPress meetup” is still hosted at the RegioHelden Office from time to time. Someone from our webdesign team invited the community years ago.
10. Invite your customers or visit them
At RegioHelden I tried to invite customers to our office as often as it made sense. I think for a founder the best kind of user research is done 1:1 in an actual human conversation. Screw those market research studies and just talk to your customer (at least in the first few years..).
“The best kind of user research is done 1:1 in an actual human conversation.”
I also sent my employees to do little 1 to 2-day internships at our SMB-customers’ companies. It created a bond and gave them first-hand insights on pain points, decision processes, and competitors. Much better than any PowerPoint presentation.
Learn through books and publications
What propelled humans’ evolution was the ability to store and share information. So, it might make sense to include traditional ways of learning into your strategy.
11. Read business books and create a book club with your team(?!)
I personally learn well through reading and reflection and have read around 100 business books over the last couple of years. Some were completely worthless, and others were invaluable. Check out my reading list with my ratings on GoodReads for recommendations. I usually tried to read summaries before I read the actual book to save time. Apps like Blinkist are great.
And why not go one step further and include your staff to read books together? At RegioHelden I created a monthly book club where my team and I would read the same book and then discuss the content. We went through 3–4 books per year. That’s much more than most employees would read on their own and the discussions were very valuable. It’s also possible to have everyone read a different book and report back to the group.
Here are some books that we read together and that had a positive impact afterwards:
- Delivering Happiness
- The Goal
- Topgrading
- Getting Things Done
- Multipliers
- The 7 Habits of Highly Successful People
- Work Rules
I also created a policy that every employee in the company could order any book they wanted to read, no questions asked, paid for by the company. No, nobody abused it.
12. Learn about successful founders by reading biographies and listening to podcasts
It’s not so easy to meet Richard Branson and brainstorm ideas with him. But you can get an idea about his thought process, mental models, decision-making, and experiences by reading his books.
Here are some great biographies and books by entrepreneurs I usually recommend to first-time founders:
- Shoe Dog by Phil Knight (It’s fucking hard to scale a cash-intense product-/marketing-business.)
- The Hard Thing About Hard Things by Ben Horowitz (It shows you the abyss of entrepreneurship. Read it if you think you have problems. Then think again.)
- Principles by Ray Dalio (Much more than just a biography and one of the best books on decision-making I have read to date.)
- Elon Musk: Inventing the future by Aslee Vance (This guy is nuts.)
- Steve Jobs by Walter Isaacson (Brilliantly written. Also check out Benjamin Franklins biography by Isaacson.)
Find more of my favourite biographies on GoodReads.
You don’t enjoy reading? Another great way to learn about successful founders is to listen to entrepreneurial podcasts. For example check out How I Built This and Masters of Scale.
Reflect and take care of yourself
13. BONUS: Get some distance and spend time alone
With all the external inputs you can get from other founders, mentors, coaches, experts, books etc., my last recommendation is this: Take time to learn from yourself!
When I was struggling with my role as CEO, as I mentioned at the beginning, I came up with a routine: Every Friday morning I would have breakfast in a café by myself. I took my notebook (pen & paper) and started to jot down my thoughts. I thought about my strengths, weaknesses, things I liked, things I disliked, what I head learned from other founders, and I reflected on my thoughts. I kept writing for a couple of hours before going into the office. It was one of the most productive times I had in terms of personal development.
Nowadays I regularly do “me-days”. That means every 3 months or so I go to a hotel or another remote location and shut myself off, just to think and reflect. I think Bill Gates copied me with his famous “Think Weeks” 😉.
In the end, you as a founder are in charge. So, no matter what other people, podcasts, or books may say, it is you who must make the decisions. So, you better take the time, reflect, and make an informed decision based on everything you’ve learned from the other techniques 🤓
I wish you the best of luck for your own personal development and the exciting path that is a startup story. If you enjoy my content, follow me on Medium and check out my other articles. Also please don’t forget to clap up to 50x 👏 for the article so that others can find it too 😊🙏.
I’d like to hear your feedback. Feel free to connect with me on LinkedIn. -Feliks 👨💻
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