I recently caught up with a friend who’d founded a company. He was at a low point: overwhelmed, sleep deprived, stressed… I listened, nodded, and said, “I remember those days.”
And I do remember them. It took years before my startup Anchor began to gain real traction. There were sleepless nights and drastic pivots, crashed servers and bad bugs. Most founders I speak to agree that the startup journey is generally discouraging, overrun with unsolvable challenges and many many mistakes.
“But there’s good stuff too, right?” my friend asked.
I assured him there was. I said that the high points, while few and far between, would be worth it. I added that the low points, while no fun in the moment, are all things that make you smarter down the road. I explained that most of his energy and concern was probably expended on things that wouldn’t matter in the long run. I told him that when I was on the journey, I too had these periods of doubt.
He asked, “What would you have done differently?”
And rather than giving him just my answer—which might have been unique to my experience, not applicable to his—I decided to do something different and write this article. I posed a question to twenty-one other founders, across many different industries from media to finance, from SaaS to urban farming. The question I asked them was this: If you could go back in time and give your younger self some advice just as you were starting your founder journey, what would you say?
Their answers are below. And I sincerely want to thank all of them for contributing and providing their perspectives.
Harish Agarwal, Chartable - Make sure you’re clear eyed about who your customer is and that helping solve their problems is a durable source of motivation.
Amy Bach, Measures for Justice - You will make mistakes. Don't beat yourself up about them. Instead, remember them to increase your gratitude for your team. I just read Jay Shetty's book and he tells people to be like salt, 'Salt is so humble that when something goes wrong, it takes the blame, and when everything goes right, it doesn't take credit.'
Dario Galbiati Alborghetti, Showday - As basic as it sounds, “do your research” as thoroughly as you can. Try to get as many insights as you get and validate as much as possible before you start. Building a business is a 10 year bet. You don’t want to go all in just based on a gut feeling. Try to leverage unique assets you already have. Industry knowledge, access to unique distribution, contacts, etc...
Kyle Downey, Cloudwall - Building something really big takes time, and while you want to be nimble and fail fast, accelerating into commitments can box you in and create unnecessary stress. My biggest errors came of hurrying.
Nina Faulhaber, Aday - Focus on the product, simplify your branding, keep a lean team, do not price your product below its worth, and turn a profit early.
Jeremy Feinstein, Zest - 1) You will fail a lot, but that certainly does not mean that you are a failure. 2) You're a marketer now. There's two sides to the PMF equation, so start getting good at the other one.
Christopher Frank, Snowday - Acknowledge and actively plan around skill-related blindspots you have on your founding team. Engineers will build, product people will strategize, business people will network, marketers will create a brand - all whether or not these are the things your company needs most in that moment.
Sarah Adler Hartman, Spoon University - 1) I had quite a bit of imposter syndrome running a company at 22, feeling like I knew nothing about anything. I wish I realized that (especially because I was so young, but also, generally) I had permission to not know what others did — so, humbly ask dumb questions, and stop caring. 2) I wish I had better understood the VC model and incentive structure when fundraising. I saw taking money like receiving a gift, which is not only entirely wrong but also throws the power dynamic and sense of moral responsibility out of whack.
Matt Hartman, Factorial - When I was starting a business in my 20s, I didn’t feel comfortable getting out over my skis. I wish I’d realized that discomfort can be a sign of growth and leaned into it.
Gareth Hickey, Noa - Before founding Noa, I didn't fully understand the 'problem' that news consumption solved for people. I understood what it solved for me and a few close peers, but not the market at large. If I were to start again, I'd focus a lot more on the 'job to be done'. Specifically, I'd avoid asking hypothetical questions like 'If I created [shiny thing], would you use it?' and instead ask 'How do you currently do X?', 'How often?', 'How much do you spend?', 'Why do you [do X]?/what would happen if you wouldn't [do X]?', and so on. This will give you a better sense of whether the market is ready for the thing you're creating.
Chang Kim (CK), Tapas - Founders need to keep practicing compartmentalizing their brain. At startups, bad sh*t happens all the time. Don’t let one bad thing affect the rest of your day. Lock up the bad thing in one zone, like locking up a beast in a cage, and move on. Think of your brain as a hard drive. Don’t ruminate on what someone said too much. Easier said than done, but founder mental health is a serious thing and compartmentalization definitely helps keeping sanity.
Matt Lieber, Gimlet - My advice to my younger self is to seek help. When I first started I thought I was supposed to have all the answers, even in the most difficult situations. This limited my quality of decisions. It also made a job that was already stressful become even moreso. Looking back, I should have sought more counsel, from both my colleagues and peers at other companies. Eventually I did this and it was more empowering for my team, resulted in better decisions, and made for a more fun ride on the roller coaster.
Jessica Mansourati, Bookself & Highlight.fm - As a woman from a minority group in Sweden, I wish I knew how little other startup founders (and investors) really know about building a startup and that they figure most things out as they go. Most male founders were going about things by trial and error and later covered them up as strategic moves. Had I known this, I would have been much less critical of myself and pushed harder for what I believe. If you ask me, this is a crucial mindset shift that needs to happen when you start building something yourself.
Shishir Mehrotra, Coda - I think probably the main thing I find myself coaching people is my two question test for starting a company: (a) do you have an idea you can't imagine not working on, and (b) do you have a partner you can't imagine not working with?
Michael Mignano, Anchor - Starting up is far less risky than you think; if you're good enough to start a company, then you're good enough to land a backup job if your company fails. Stop overthinking the downside scenario and get to work.
Avi Muchnick, BurnerPage - If I had to give myself one piece of advice, it would be to schedule a weekly thinking meeting outside of the office (ideally in a completely new spot each time). I have found that the best decisions my teams and I have ever made all had one thing in common: We were not inside the office at the time we made them. Breaking out of a routine uninhibited our thinking and collaboration in magical ways. Making a routine out of routine-breaking behavior seems ironic, but it's such a valuable way to force your brain to reset and think strategically with fresh eyes. I wish I had known that since day 1 of my startup journey.
Priya Patel, Wellen - 1) There are people who add energy and there are people who drain energy. Prioritize finding and hiring the former. If you accidentally hire the latter, fire fast. 2) A startup is a marathon, not a sprint. Rest, exercise, eat well, take real vacations.
Tobias Peggs, Square Roots - If you've got founder DNA, you will likely have lots of ideas for cool things you're excited about that should exist. But you will have fewer ideas for important things that need to exist where people will understand the true value and be prepared to pay for it. It's worthwhile taking a minute to make sure that your new thing is both. I'm all for speed being a major advantage of start ups. But you don't need to be at that hyper speed when you're deciding what that startup should be. Take a minute, get that right, make sure you're doing something important that you're also wildly passionate about. If you hit that sweet spot, the startup rollercoaster you've strapped into might just be a little bit smoother than others.
Omer Rabin, Entor - As you kick off this new adventure as a founder, you'll find a lot of things different than being a senior executive in other people's companies. Many of these will surprise you, even though you sort of knew they are expected. One thing you should know, however, is that your superpower will only come into play when you're doing what you like, focusing on a problem you care about, or solving a pain for a persona you know and love. You're going to spend 18 and sometimes 20 hours a day on this problem, market and product - you better feel it in your bones and be ready to wake up and get out of bed (at least on most days) with a killer attitude. The path ahead of you will force you be creative, passionate, focused, agile, faithful and excited - and you truly can't fake them all.
Molly Stern, Zando - When I wake up most days – literally, as I open my eyes, I feel I know there is something specific I need to do for our business. Sometimes I’m seized by raw, unpleasant concern, but often I wake with an understanding, a plan, a new question to ask. This is, I think, the finished stew of assimilated feedback, or worry, or the not knowing from the day before. I’m not always right, but in the early morning I feel resolved, and I sally forth. This I like. What I don’t always enjoy is the shroud of the Foggy Middle - the external elements (life, other people, industry-wide headwinds) that challenge my morning certainty. I descend from the peak of clarity into the quick-sand of unexpected events, contradiction or diversion. But inevitably the day ends. And so far, like Groundhog Day, I wake up again with an approach, a question, a plan. So, maybe once a business is truly clear you get to sleep in. But then it wouldn’t be a startup anymore.
Rana Taghdisi Argenio, 10 Grove - Forge your own path. There's no guaranteed playbook to success. Everything in the world is the way it is because someone decided to make it that way. When starting a new business, following the path that was successful for others is more likely to result in your failure as innovation in brand or product is no longer enough... It's your growth strategy that builds the true, defensible moat.
Nir Zicherman, Anchor - Meet and talk to more people like everyone listed above. They can offer great perspective. You’re not the only person going through this.
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