First-time founder mistakes

Sharing all the things I did wrong so you can do better

It’s interesting how, when you start a company, you hear lots of experiences from others or read about them in smart startup books and think you’re well prepared. Then you experience them first hand, make all the mistakes there are and later on it finally makes “click”! You understand what the others were trying to tell you at the time.

This is now another try to summarise those funny not-so-funny first-time founder mistakes and what I learned to do instead in my second round.

Team

1. 🫱🏼‍🫲🏽 Co-Founders: First off — It’s so damn hard to find the right co-founder — it’s truly like marriage and if you find *the one* you should never let them go :) Startups do to the relationship between the founders what a dog does to a sock: if it can be pulled apart, it will be. Honestly, so many things that can go wrong here, so I’m just capturing a couple of things that I experienced myself in several attempts to start companies with others:

   1. Ideally, find people you’ve been working with before — having trust and no ego in the room is the most important baseline for productivity and shipping great stuff — building a startup is already hard enough, you can’t waste time and energy on internal politics. If I were to choose again, this is what I would look for first.

   2. It’s a lot harder to start a company with people you haven’t worked with before. Mainly, as it is difficult to do your due diligence correctly. People say they are acting a certain way but then do the exact opposite later on. Sometimes you don’t have a choice though. So if you decide to go with someone you don’t know, I recommend working on having a TON of hard conversations early on (e.g. at Remi we built our own Co-Founder Matching Questionnaire), ideally doing a stressful test project together. When you then decide to get going, give them the benefit of the doubt. Trust is so important!

   3. For me, the most important criteria are the following:

      1. Must-have: shared characteristics, values & ways of working

      2. Must-have: existing trust base or benefit-of-the-doubt attitude

      3. Ideal: we have a complementary skill set

      4. Ideal: we’ve worked together in a previous venture

      5. Ideal: we’ve become friends (ergo, existing trust base!!)

      6. Ideal: they’ve worked in a startup before

      7. Nice-to-have: they’ve founded a company already or started a side business

      8. Nice-to-have: they’ve worked in a leadership role before

   4. Once you’ve found your co-founder, I think what’s most important is to create clear roles & responsibilities. Ideally, work with people who are 10x better than yourself in other areas. If that’s not a given and you’re similar in your skill set, create clarity from the start of who does what. Have those hard conversations early on. You don’t want to have the debate over and over again later on.

   5. Another clear red flag and opportunity I almost fell for 🚩 People who want more shares because they had the initial idea. An idea counts nothing — everyone has ideas! In the end, it’s all about the team and the execution. Also, usually, the solution changes over time (at least once).

2. 🕵🏼‍♀️ Hiring:

   1. First-time founders many times think that the more they hire, the better/faster they can solve their issues. Have a problem? Throw money at it! I had this belief in my first venture. “How many people do you have on your team?” is a common question you get asked. It’s a dumb status game. Similar to “How much have you raised already?” or managers in big companies who push their egos by the amount of talent they gather in their teams vs the outcomes they deliver.

      1. What I learned in Round 2: Stay as lean as possible for as long as possible. You’ll stay a lot more flexible. Focus on finding product market fit vs. company building. Everything else is a distraction. Think wisely about who you want to hire and what for. Test things yourself before you double down on a skill set you’re looking to hire.

   2. Many first-time founders also think, that they *just* need someone to do the job which is why they hire a lot of working students and interns, completely overwhelm them, and don’t even have time to help them develop. Usually, it’s a cost-saving measure but most of the time, it’s a distraction.

      1. What you should do instead: Hire less but experienced people (ideally as part of your founding team) vs a lot of cheap and inexperienced ones. You can start developing new talent, once you grow but in the early days, you need people who take action & can work in solitude. A 4-person team (e.g. a product person, an engineer, a designer, and a marketing/community person) can get you very far from the get-go.

   3. Do everything yourself vs outsourcing: In my first startup, I tried to do almost everything myself — especially because resources were scarce but also because I wanted to solve it by myself. Many times it took me much longer because I wasn’t reflecting that I needed help or asked for it fast enough. It drove me into depression in certain periods, as I wasn’t getting any energy anymore from my day-to-day work and was doing things that I clearly wasn’t good at or enjoying. Short phases like these are normal, but they shouldn’t be the norm. You need to play to your strengths and partner where you’re weak. How?

      1. Co-Founders / Founding Team: Ideally you find a setup where you can completely focus on your strengths from the start.

      2. Build a network: Gather advisors, investors, strong operators, and other founders around you who are in a similar stage or 1-2 steps ahead to bounce off hypotheses. A small improvement in navigational ability can make you a lot faster because it has a double effect: the path is shorter, and you can travel faster along it when you're more certain it's the right one.

      3. Also, work with freelancers in situations where you want to test certain things and need additional expertise/resources, but aren’t sure yet if you should double down and hire someone full-time. E.g. some roles we clearly shouldn’t have hired full-time so early on. It’s a business risk and in the worst case, you need to let them go sooner or later. Lose-lose.

🗺️ Location

1. Fully Remote vs In-Office vs Hybrid: My first venture was completely remote — we didn’t even have an office. That’s maybe because we were solving for remote culture ;) maybe also because it was at the peak of the pandemic. Either way, I still am a big believer in remote work and the flexibility that comes with it. I do believe though, that for two company phases, it doesn’t work out.

   1. New Venture: When you’re starting a new business nothing beats the quick conversations you have and iterations you can make when sitting in one room. The energy you create is also a completely different one — in good as well as in bad times. It’s a different kind of magic.

   2. Pivot: When you’re forming a new team or when you’re in a phase that requires a pivot or fast changes, I’d argue it’s a lot harder in a fully remote setting.

   3. It can work but not as well as it does for hybrid & in-office, mainly because remote requires a lot of structures & processes that need to be built up from the start and those are poison for the creativity & fast iterations you need in startups to constantly act and adapt.

🧠 Mindset

1. Decision Making: Analysis paralysis is what kept me at my first startup from moving, iterating, and learning fast enough. Mainly because we had hired too big of a team already after raising our pre-seed round before even hitting PMF. We therefore weren’t as flexible anymore as we were at the beginning when we were still in our experiment + test phase building our MVP.

   1. In Round 2 I learned: Speed defines startups. Focus enables speed. So what it takes is radical decision-making! Take decisions fast to iterate and learn fast. Why?

      1. You’ll create double the costs by delaying decisions.

      2. Your chances of winning will increase! Simply because you shoot more on goal than other people. Decisions are cheap and reversible. Ship it and you can still do quick iterations (counts for product decisions, team members, etc.)

      3. It’s important to always be on the action side of things. Don’t wait for other people or other information. The way to figure out what to work on is by working. If you're not sure what to work on, guess. But pick something and get going. You'll probably guess wrong some of the time, but that's fine.

2. Energy Management: What I underestimated in my first venture is paying enough attention to energy management. They say it’s a marathon, not a sprint. And they are right. It’s still so very exhausting and even if you have the best intentions they easily slip. What I learned in my second venture:

   1. Only a healthy body and mind can create clarity of thought and keep the main thing the main thing. Breaks are important to being able to see the bigger picture. Be smart about it.

   2. The more passionate you are about the problem you’re solving the more you’ll enjoy the journey and have fun! People work a lot harder on stuff they are passionate about and they can do it also for much longer. To be completely honest: In my first venture, I wasn’t passionate enough about the topic — I was very curious and interested but it didn’t keep me energized for long enough.

3. Show don’t tell: First-time founders many times spend all their time doing PR, interviews, and going to conferences. I did the same. Don’t get me wrong, some of it might be worth it, e.g. for branding purposes, recruiting talent, and building their network but most of the time: it’s a distraction. It’s pushing the ego more than it is bringing your business forward.

   1. Instead, choose wisely: If it is a conference where 90% of your customers will be or a news outlet that’s mainly read by your target persona — do it! If you’re currently hiring and it is a podcast that most likely attracts interesting talent, go for it! But if it’s just a media request that pushes your ego, you better leave it.

4. Focus on yourself, not on others. It’s so easy for a first-time founder to get stressed out by all your competitors. The best thing you can do for your business is to be aware of what’s out there but to focus on only yourself. Keep shipping, and be one step ahead of the others.

5. Opinions loosely held: If you are about to create a category or shape a market you need to do things differently than others. What’s needed is a learner mindset. You need people on your team who are intellectually open to discussing different ideas. People who aren’t married to their ideas, but that are looking for the best possible outcome. People with strong opinions, loosely held.

🏗️ Product — as I wasn’t in charge of it, just a few observations:

1. Reinventing vs Optimizing: In my first venture I thought we needed to create a new category and that meant having to invent something completely new. We thought all of it needed to be new. The problem with this thinking is that you are trying to reinvent the wheel and then also need to create awareness for the new solution (meaning, spending a lot of money on education).

   1. Instead in Round 2, we did the following: In an existing market, where demand and willingness to pay were already validated, we focused on doing one thing 10x better than everyone else. The chances are much higher for winning.

2. Big Vision vs Killer Feature: In our first venture we started super iterative, then when we started raising money though we had to come up with a big vision of where we’re headed. Not just for investors, but also for ourselves as a north star as well as to convince key talent to join us. At some point, we sadly got carried away by our vision and thought way too big, meaning we were building a way too big solution from the start instead of focusing on identifying one killer feature/flow that works (your so-called “wedge”).

   1. In round 2 instead, we focused on: Defining our wedge, in this case, the single-player mode for our product (especially important for network-based and product-led teams to consider), and then making it 10x better than what’s out there in its simplest form vs branching out in different directions before nailing PMF.

3. Ship it: In our first venture we were so embarrassed by our first concepts & prototypes — it took us way too long to go to market and test our idea. Eventually, we overcame our fears and learned so much more once our product finally was out in the wild. Our early adopters appreciated even more being part of the journey and seeing the progress. These early believers will be those who keep supporting you later on.

4. Must have vs nice to have: In our first venture, we identified way too late, that our solution was regarded mostly as a nice to have. Before we were able to pivot to another feature, we ran out of money.

   1. Instead, solve the highest-priority problem you can identify with your customer. Build a must-have vs just a nice-to-have. If they are not already investing in the problem, paying for an alternative, or are already looking for a solution, it’s probably not that urgent (especially in B2B).

5. User Feedback: Your job as CEO of a startup is to hear the harshest feedback from your customers, put your ego aside, listen, then go fix shit. In our first venture, we weren’t intellectually honest to ourselves that our product was only mediocre. There was interest, but no strong pull and we moved too slowly / didn’t take the decision to fix it. Btw, the same happened in our second venture: we noticed that even we didn’t want to use our own product. Luckily we understood that we needed to pivot and took a fast turn.

6. Some other learnings on product:

   1. Onboarding: Don’t underestimate the Onboarding experience — it’s the first impression of the product.

   2. Simplification: radically simplify the product experience. What does your product really need to work? Leave out whatever doesn’t need to be there (also called minimal lovable product).

📣 Distribution

1. First of all, sadly no magic saves a bad product. Marketing is no substitute for a great product with happy customers BUT nothing can amplify the success of those efforts like good marketing. What good marketing looks like:

   1. In the case of a new category, it requires proving that the category actually exists

   2. In the case of an existing category, it requires redefining the category around your disruption

   3. Either way, it takes time to convince the market of your POV.

2. Ideally, your product solves for PMF and distribution early on, as Andrew Chen nicely put it: “(…) startups end up needing both:

   1. an insight about customers that gives them product/market fit

   2. an insight about distribution that creates traction”

   3. he writes more on it here

3. Target Audience: What’s important to mention here: Choose a niche audience and solve a high-priority problem for that very specific audience!! Then, it’s all about quality over quantity. Focus on making a small number of users love you rather than a large number kind of like you. Start with 10, then 100, 1000, and so on.

4. Brand: Another thing I learned is how important building a strong brand & community is to differentiate yourself. At pre-seed, you don’t have much money to spend on marketing. Also, most people don’t like ads anyway, and ad dollars spent get increasingly expensive and unsustainable for brands overall. Most VC-funded startups run paid campaigns chasing sales with no investment in their brand & organic channels. You might hit revenue goals but as soon as you stop spending, sales will stop. Unless you have a big budget, you're going to hit a wall soon.

   1. Instead, start with a minimal lovable brand. In the early days, the best marketing you can do for yourself is build a (personal) brand by talking about your vision, and your product, documenting your story + adding value for your customers (e.g. creating content to help them grow/solve their biggest pain points). Don’t just talk about yourself.

5. Focus on one key distribution channel: Usually one says: “Don’t put all your eggs in one basket”, and that’s true. But in the early days, you need to focus & prioritize. Resources are scarce and it won’t work if you are everywhere just a little bit. Test and iterate quickly but then choose one channel to go all in. In my first venture, this was Linkedin, in my second it was Twitter. Make it dependent on your audience and where they hang out most of the time. Once you nail that channel, you can branch out and expand.

6. Create a movement: Customer attention is hard to get today. Don't just sell products -- inspire change. The best businesses build movements. This is how you will win the hearts of early customers, employees, and important stakeholders.

7. Build Community: Just build it & they will come? Probably not. Start building your audience while building the product. Building relationships with early adopters of your product will lay the groundwork for a vibrant community later on. When starting a company, don’t be afraid of the things that don’t scale. You need to fully immerse yourself in the community and become part of it.

Phew! Got a bit longer than expected. Oh well, hope it is of value! Would love to hear more about your f*ck ups, mistakes, and learnings 💥 Drop them in the comments below.

Enjoyed this article? You might also like my latest article about unveiling the second-time founder magic.

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About the Author:

Valerie is a founder and passionate community builder. More here.

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Her newsletter is sent every 2-6 weeks directly to your email inbox. In this newsletter, she captures thoughts, good reads & learnings. Think 0-1, early growth & GTM strategies, community building, brand & product positioning as well as her founder journey.