2 Years Ago I Quit My 6-Figure Job To Start A Company. I wrote this letter to my past self.
It’s been 295 days since my last blog post.
The reason for the gap? I’ve been working.
There’s much beneath the surface of that simple headline. I’ve learned a lot in that time. And as I reflect on those learnings, I think about what advice I’d give to myself back when I started.
TLDR: If starting a company, make sure
1) you know what you’re getting into
2) you understand your customers and the space and
3) you’ve asked yourself ‘why’.
Feel free to jump to any section specifically; I know this is long.
Rewind: Feb 2015
After entering Startup Land — I went through an acquisition, worked at a big company, and landed an offer at a startup paying me almost triple what I made just two years prior.
It was a whirlwind journey that left me infatuated with this new world; one with a never-ending list of possibilities and things to learn. I was intoxicated by the process of building something from nothing. And became convinced I needed to start my own company.
My conviction quickly turned to obsession. I had to escape my day job and make this my reality. So I took the leap. I quit my well-paid position for the wonderful compensation of $0 per year — but the career I longed for.
Fast Forward: Today
The last two years have revealed how flawed my logic was. While I have plenty of work and learnings ahead of me, if I could talk to myself two years ago, the below would be my advice.
This advice should not be construed as gospel — my views and knowledge on this journey continue to evolve. It is my hope in writing this, that the lessons learned can reach, and be helpful to, an aspiring entrepreneur who may be in a similar headspace to that of mine two years ago.
Dear Me,
You’re young. And stupid. I come from the future — so let me school you, fool. Don’t interrupt. Just pay attention and take it to heart. You need to think about a few things…
1. The Decision To Start
I’ve heard you say, “I want to start my own company”. And I get it, I do. But let me tell you — this is extremely misguided thinking.
This thinking is derived from the romanticism surrounding startups and entrepreneurship. With success stories being glorified in movies, pop culture, and daily TechCrunch articles.
Newsflash: startups are fucking hard. Those massive success stories, while attainable, are nonetheless anomalies. Read about the power law of venture capital. Even if you go into it knowing it’s hard… I promise you, it’s harder than that.
Don’t take this pursuit lightly. If you intend to be successful (you do), you’ll need to dedicate the next 5–10 years to this single mission. Considering the human lifespan and the finite resource that is time… this is a significant investment.
You’ll need to allocate the majority of your time and, more importantly, mental energy towards this one goal. You’ll need to sacrifice money, relationships, and opportunities in an effort to will your vision into a reality.
And even after all of that… the odds still say you will fail. It’s a daunting proposition. But the brutal, honest truth you must recognize.
2. Founder/Market Fit
As a founder, you need to have an incredible passion and understanding of the market you’re in and the problem you’re solving. This dynamic, referred to as “Founder/Market Fit”, is the single most important question to ask before starting.
Again, this is an idea you’ll need to pursue for the next 5–10 years (the average acquisition is 7+ years, the average IPO is over 8). This is a market you’ll have to dedicate prime years of your life to be obsessed with.
The Takeaway: You must truly give a shit about what you’re doing. Many shits, really.
You need to care deeply about making your vision a reality. About helping the customer you’re serving and improving the industry you’re in. About the company you’re building and the people who join you for the ride.
Don’t start a company because you “want to”. Or because you “think you should”. Or because you think it will “give you freedom and flexibility” (lol).
Don’t start a company just to start a company.
Start a company because there is a problem you understand intimately and you can’t sit around anymore without solving it.
And then, still don’t start the company. Start solving the problem.
Often people fall victim to confirmation bias. They spin their thoughts and the information around them, convincing themselves that starting a company is what they need to do. They tell themselves they love XYZ industry and are obsessed with fixing it. When really they just want to get out of a job they hate or find some work/life balance.
This “grass-is-greener” point of view is easy to fall into. But you need to think objectively at what you’re trying to do and why.
Anyone can start a company. But starting a business you’re not passionate about is setting yourself up for failure. Because…
- You’ll be thinking through and dealing with the ins-and-outs of this business every day, every minute — for years to come. If you hate it, you’ll be miserable and it will always feel like “work”.
- If you’re not passionate about it, that means that someone else out there, who is passionate about it, is better positioned to solve the problem. Play to your strengths, favor your interests, and give yourself the best chance to succeed.
Mostly, ask yourself “why?”. Why do you want to start this company? And be brutally honest with that answer. This sort of introspection can open up thoughts and ideas you didn’t know existed before.
If you decide it’s worth pursuing, your next step should be conducting extensive research to understand the industry and the solutions available. And more importantly…
3. Talk To Customers!
I know you’re a product manager and you have great wireframes and the designs look beautiful and… no. Stop. If you’re contemplating starting a company or building a product, this is the ONLY thing you should be focused on.
Talking to customers will be highest yield activity you can spend your time on. At any stage, talking to your customers provides incredible insight, but it’s markedly important when you’re just getting started. The learnings and takeaways from these conversations will guide you on where to start and where to focus your attention.
You need to understand your customers intimately. Ideally, you should be one. Understand who they are. What problems they have. How they solve them today. And, with a big enough sample size, how you can help them solve these problems in a better, more efficient way.
After doing this you’ll wonder how you ever thought about starting a company without talking to customers first.
And lucky for you, you don’t have to quit your job or invest any money to do this. Just talk people. Call them. Write an email. Take them out for coffee or drinks. Talk to as many as you can. Be relentless — like the future of your company depends on it. It does.
Related Note 1: You may want to create a blog, instead of building software, as your “MVP”. This could be a powerful way to dive deep on a topic, understand your customers, and build an initial audience.
Related Note 2: Here is a great list of user interview questions you can use.
4. Have A Co-Founder
I’m not saying solo founders can’t be successful but it does carry unique challenges. While you won’t be subject to co-founder infighting, with a second or third founder you can: get 2–3x the amount of work done (notably in the early stage where everything is manual), apply different perspectives and skill-sets to the same problem, and have a more appealing pitch to investors (some avoid solo founders).
Perhaps the biggest reason is that the emotional ups and downs of the job can be draining. Founder depression is a real thing — something I’ve experienced myself. It’s helpful to have someone in the trenches with you, who understands the details of what’s happening. Someone who can sympathize, support, and work with you to solve problems.
5. Have A Support Network
Co-founder or not, you must have a solid support network around you. This network can take different forms and provide different types of utility. Your personal network helps take care of the emotional layer — the baseline for operating each day. Surround yourself with friends and family who cheer you on, understand the stresses and demands of your job, and can be there to talk when called upon.
A professional network is equally important. This network serves to give you honest feedback. To keep you grounded and provide educated, actionable advice. They can help you brainstorm and solve problems. They can make introductions to people valuable to your business, and help grow the network over time.
Note: Don’t forget to give back to these networks. As a rule, try to give more than you receive.
6. Thick Skin
The support networks help but only you experience what it’s like to be in your shoes every day. So you’ll need to have (or develop) thick skin.
Life as a startup founder is riddled with more downs than ups. More “no” than “yes”. And more caffeine than sleep. I can’t say it’s the healthiest lifestyle choice. Early-stage startups demand a lot of time and sometimes you won’t see immediate results.
Understand that things are never as amazing or as horrible as they seem in the moment. Keep a level head and remain focused on your mission. Be open to feedback but persist on the things you know to be true. Don’t let one meeting get you down, or another convince you that you’ve made it. Take the hits, keep pushing, and hustle on.
7. Understand Investors
Always seek to understand your audience, no matter what you’re doing. Raising money for your business is no different. Understanding how venture capital works is imperative to raising that money. While not as important as understanding your customers and building something they love, if you don’t understand the motivations and incentives driving the person across the table, you aren’t setting yourself up for success.
8. Core Values
Establishing your core values at an early stage is one of the more valuable things you can do as a founder (after research/talking to customers).
It doesn’t matter how small you are. 1–2 person companies should do this. It may seem unintuitive at that size, but trust me (I’m from the future)… take the time to define your mission and core values. The good news is — they should already be inherent to who you are and what you do. You just need to talk it out and write them down.
Not establishing your mission and core values is the equivalent of sailing in a vast, open ocean without a compass.
These will inform everything you do moving forward. Hiring. Product. Strategy. Prioritization. Metrics. Goals you set. Performance reviews…. it’s the baseline for gauging everything.
The culmination of all of those decisions is what creates your culture. And culture is created whether you craft it or not. So you might as well be deliberate about what you want it to be. There’s nothing more important about your company than the people. And culture is what determines the type of people you hire, the talented people you retain, and the success of the product/service you all create. You cannot ignore this.
9. Taking Care of You
We touched on your emotional wellbeing within the context of your business — but there’s more to it. A few points here…
Physical: Seemingly obvious, this portion of personal health is often the first to suffer. For me, I deprioritized my physical health because there was nobody holding me accountable. For everything else in my life there were people who counted on me. My health was my problem, and when days got busy (they always do), I would skip. It wasn’t until I reframed this in my mind that I started making my health a priority.
You need to be at your best for your immediate network. You need to support your family, friends, and colleagues to the best of your ability. And part of that is making sure you’re healthy, focused, and capable of being there when needed.
Reading: Think of it this way… there is an opportunity cost to not actively reading.
New ideas are formed when your brain connects different thoughts, concepts, or experiences together in your mind. Applying a theory, story, or solution that you read about, to a problem in your life… that’s where creativity and innovation live.
Reading is the avenue to get you there. If you can only pull from your existing arsenal of experiences, vocabulary, and ideas — then you significantly limit your ability to solve problems and think creatively. This also applies to organizations. Valuing and recruiting for diverse perspectives makes your team better equipped to solve problems.
Writing: If reading gives you the ammo to work with, and your brain is the weapon — then writing is the trigger. All those creative thoughts and ideas are effectively useless if you don’t get them out.
On top of that, writing has this wonderful compounding effect. It makes room for more creativity. As you begin writing, you’ll find that new ideas start coming to the surface. Getting those top-level thoughts out clears way for a whole new layer of ideas to rise up.
Make sure you write every day (morning is typically best). Challenge your brain with interesting questions and scenarios. And take time to revisit and review ideas. Reading your own thoughts from a different time and headspace can often be the same as reading someone else’s prose. It can help to place you, mentally, back in a different space.
10. Keep Learning
Understanding that you don’t know shit is one of the most empowering mindsets you can take. That’s not to say you shouldn’t be confident, but there’s an important difference between confidence and arrogance. Putting on a false sense of expertise is actually detrimental.
Fuck “fake it til you make it”. Know what you don’t know and seek to keep learning and improving. This will give you all the confidence you need because you won’t be afraid to say you don’t know something. To ask for help. To learn and tackle new challenges in innovative ways. That’s how the best get better, solve problems, and succeed.
Keep on pushing,
You +2 years
This letter is by no means a comprehensive guide on how to start a company. It’s also targeted at a company’s super early, origin stage. Each of the above could be it’s own post and plenty of lessons simply didn’t make the cut.
The point of this isn’t to delay the action. As a startup founder, all you should be doing is taking action. But those early actions could be this diligence process — helping you understand what you’re signing up for and preparing you for success.
At a certain point there are diminishing returns — where that extra book, blog post, or phone call isn’t going to make the difference. At that point, the only way to learn more is to dive in and keep learning as you go. Entrepreneurship is like a pool in that way. Just make sure you’re not oblivious to the lessons above and you’re making this massive life decision for the right reasons.
After that… push forward and hustle to make your vision a reality. It’s on you to make it happen.
