What this article is NOT: advice on how to start a successful company (I’ll let you know if I figure it out)
What it MIGHT be: anecdotal advice on how to get the most out of yourself in year one
*tactical advice & TLDR at the bottom*
1) Never stop swimming upstream
Are you uncomfortable every day? Continuing to be able to answer yes to this question is the quickest way to measure if you’re doing your job as an early founder. For me this started with things like making this website from scratch or unsuccessfully pitching to investors. It’s evolved into showing up on last minute radio shows and handing potential customers business cards while on airplanes.
It’s kind of like the 90’s show Double Dare 3000; the part at the end when kids run through the obstacle course collecting flags for prizes. There are very few instructions on how to go about the course; dive headfirst into a pit of slime, glide over a human-sized rolling pin. All you know is the goal: to find every flag as quickly as possible. That’s company building. And every day you better have slime on your face, or else you’re not making progress.
2) Resist the urge to build a team
The deeper you get in your career, the fewer opportunities you get to spend 100% of your time on yourself. If you’ve already led teams, you’ll have an especially hard time fighting the urge to recruit. In fact, most founders come in with a few people they know they want to hire early on. Almost every founder is a great campaigner. All of this will beg you to build a team… but don’t. This is a unique opportunity to focus on you.
It’s a moment that 0–1 affords you in a way no other job in the world does. You get to design a strategy and execute every aspect of it. It is because of the six months where I did everything alone, that I would now run circles around any earlier version of myself.
You’ll embody a generalist skill set in a way you never have. When you finally do build a team, you’ll be far more understanding, empathetic and grateful for each new role.
3) End your day with the best call
One of the clear differences between being a manager in corporate America and a business leader in startupland is that almost every meeting is external. You’re negotiating with a vendor, screening a candidate, trying to keep legal fees down, impressing a 22-year-old venture capitalist, or chasing down a lead. A founder friend once compared it to doing 7–10 job interviews every day. It can be exhausting even on a good day. Way too often after work I would be quiet, in my own head and incapable of conversing with the non-work humans in my life.
So then I filled the end of the work day with founder calls. These calls have a hit rate of being fun about 98% of the time. They are your peers. Regardless of stage, experience, industry or location; they get it. It can be a chance to be absurdly vulnerable. Or at other times, completely amazed by their ideas and inspired by their energy and passion. And now I’m just more fun to be around afterwards. If you take any of my advice, pick this one.
4) Recognize that progress is born from the depths
When I look back on the past twelve months, it is probably the year that I have grown the most in my entire life. But sometimes it’s really hard to see the forest through the trees. It starts with an overwhelming feeling of loneliness. You find yourself in a daze long enough that your screen goes black and your reflection is staring back at you. In meetings you use the word “‘we” as a safety mechanism for not feeling totally alone.
Then come the downswings. You hear the words “we’re going to pass for now” or “its a little early for us” meeting after meeting. Other’s poke holes in hundreds of hours of work and ask if you could change the entire concept of your business. And just when those deep, dark moments start to break you, you find yourself.
As another founder put it “you hunt to eat”. Survival instincts kick in that make you create new ways to be effective. You throw out the ‘sage founder’ book advice and blaze your own path. It’s often a half-baked plan applied with maximum effort. But by doing the wrong thing a lot of the time, you start doing a few of the right things.
Eventually, the resilience you build in an ocean of failure becomes intoxicating. You go from wondering whether you were good enough at the end of a meeting, to being good enough before the meeting even starts. Your definition of success begins to stray entirely away from the world around you. And only then, as the roller coaster continues to rise and fall, do you actually start to enjoy the ride.
This process is chapter 1 of the struggle.
5) Draw clear lines in the sand on culture
This can sound generic. There are infinite articles about setting culture on day one. But I actually think it’s easy to unsubscribe for that same reason. Effectiveness = simplicity. Think about things you wouldn’t compromise, even if it meant keeping your company alive. Mine are:
- Don’t work with jerks
- Big ambitions > big resumes
- Perpetual learning
Let’s play this out. If I don’t raise money because the only person willing to give me a check is a jerk that I don’t want to spend time with, it’s a hill I’m willing to die on. If I hire someone who has a clear, determined vision of where they want to be in 5 years, but is still relatively junior or lacks experience; it’s probably going to cost us in short-term execution and that’s okay. If everyone at my company spends at least part of their time teaching themselves something new, it means there will be a lot of failed experiments… I’ll gladly invest in those lessons.
On the flip side, if we succeed it will be as a group of people who are enjoyable to be around, who can take on any challenge, and are learning every day of our lives. Envisioning this as our company’s future gets me fired up. It feels simple. It feels like a place I want to work; with people I want to work with.
6) Remind yourself that a founder looks like you
There was a time in my life when I thought to be a startup founder you had to be one of those kids in their parent’s garage taking apart the living room TV. Successful founders dropped out of top-10 schools. They loved math problems. They swindled 8th graders into a cheeky business deal in the 5th grade. They wore glasses and black t shirts. Their parents were founders. They lived in California. Basically everything in this book:
The more founders I meet, the more my perception of the ‘founder’ archetype changes. The most successful ones I’ve met are just people, with wildly different backgrounds and experiences; doing something they love, building for people they care about.
The broader advice is to caution how you listen to the world around you and to sometimes not listen at all.
7) Measure success untraditionally
The most common external measurements of success as a startup founder are things like
- raising VC money
- having millions of users and/or meaningful ARR
- exits & IPOs
At least one, and likely all three of these things will take a lot of time to happen (if they do at all). Because everything else at a startup moves so quickly, when these things take so much time it perpetuates the feeling of failure. Somewhere deep in this failure, I started asking myself for a new definition of success. I knew it couldn’t be the kind of success that gets high fives at happy hour. This version was just going to be for me.
I started writing down small things each week without realizing they had become my new goal sheet. One week I wrote “see how many meetings you can have without talking about your product/concept”. What that really meant was being a great listener. Another week was “set up your most important calls at the end of long back to backs”. The intent here was to be so exhausted, I didn’t have the energy to be a salesman and instead would maybe connect more deeply. Mixed results. One of my favorites was “take 5 walks”. Quite literally I was reminding myself to go outside.
Almost all of these “goals” violated the golden rule of being clearly measurable, but I wasn’t measuring them any way. Just asking something of myself each week was more important than performance. The truth is I probably failed miserably at most of them.
It was almost like setting a workout goal each week without a serious intention of measuring it. The one commitment you were making to yourself was that getting more fit was on the agenda. You might not get a 6-pack anytime soon, but it might also be much more sustainable than P90X.
Slowly, sneakily, I grew.
I think true founder success is best understood by those that have lived through the failures. Giving a contract employee a full-time offer because you can pay them for the foreseeable future. Getting unique, critical product feedback. Being vulnerable. Doing a non-work activity in the middle of a weekday and not letting yourself feel guilty about it. Pressing the publish button.
As I’ve started to achieve a few more traditional versions of success, I find they mean so much less to me than my own ones. Those high fives at happy hour feel good in the moment but fade fast. What sticks around is everything else. I’ve grown through self-awareness and compassion. By doing so, I’m more committed than ever to asking myself for more.
8) Make your network your boss
A few years ago, simply sending a LinkedIn request to someone I didn’t know or hadn’t talked to recently felt weird. These days, I will literally ask anyone (stranger, family member or anything in between) for help if I think they have an ability to add value. Like everything in life there is a learning curve to being effective. I got better at what the ask looked like, while also building a ton of equity by giving first. Simply put, it has changed everything I do. Because the reality is the hardest part about being your own boss, is you don’t have someone to learn from.
Take the biggest problem you’re trying to solve and ask 5 people you respect how they would solve it. It can even be in an email or on LinkedIn. By making your network your boss, you open yourself up to an incredible diversity of knowledge and perspective. You won’t believe how willing they are to help.
9) Surround yourself with ‘our timers’
Of the hundreds of coffee chats I’ve had over the past year, I can usually tell in the first 2–3 minutes whether it’s going to be a fun conversation. It’s the distinction between ‘my time’ and ‘our time’.
You can ID a ‘my timer’ with the following signals:
- Starting a meeting without introductions or any small talk and diving immediately into short ‘I’m the boss’ questions like “why are we meeting today”
- They ask some version of “how can I help” but their tone points to help being a burden for them
- They likely won’t share anything about themselves unless prompted
- They won’t smile or have any visible reaction to the things you say
- Whether they intend to or not, they do an exceptional job at sending the message ‘I am more important than you’
The harder part is that there is no consistency to what a ‘my timer’ looks like on paper. You won’t be able to ID them before a meeting and therefore you’re never going to stop running into them. And unfortunately you will always be left thinking ‘well that was a waste of both of our time’.
What can you do about it? Cultivate relationships with ‘our timers’ and be one yourself.
Signals:
- They usually start off sharing something about themselves or asking to hear about you, your story, your background or what you are up to
- They might start a conversation with a shared interest from looking at your profile or company website
- The conversation is always a two way street of sharing, commiserating, listening, asking questions, providing candid perspective
- A healthy amount of smiling
- You leave the meeting feeling energized, excited, inspired
My commitment to myself over this next year is to surround myself with ‘our-timers’. And perhaps even more important, remind myself every single meeting to be collaborative, a great listener and a genuine human being.
10) Take a stance
As an operator, having an opinion can feel scary. You think ‘what if I say the wrong thing’. But by falling silent, you miss the conversation altogether. I made this mistake early on. I stayed silent thinking that no one cared what I had to say.
But once I finally started sharing what we stand for, and what I stand for… I realized the amazing power it had in building an early community. It infused cohesion into our brand and product. Then I’d find myself nervously smiling when a new acquaintance engaged me about an opinion I shared publicly, because I wasn’t sure what side they were on yet. But now I realize that doesn’t matter either. The important thing is having the conversation.
Tactical Advice (in list form)
Fundraising order:
(1) family
(2) former bosses/clients/colleagues
(3) angels in your network
(4) angels that are 2nds (ask for a warm intro)
(5) VCs (see below for inbound shortcuts)
(6) anything else*Suggestion: get at least one person in each bucket before you move on to the next*Best founder communities:
- NON-DILUTIVE accelerator or startup programs
- alma-mater(s) groups (create one if it doesn't exist)
- industry-specific slack communities (DM me for FinTech)
- location-specific slack communities (DM me for PNW)Sourcing talent (in order):
- your close network
- advisor/investor recs
- founder/hackathon events
- LinkedIn network
- alma mater(s)
*Job ads are a waste of time*Sourcing beta users (pre-product):
- collecting emails on a website/landing page
- engaging with interest groups on social media
- answering questions relating to problem statement on public forums
- creating a strong brand voice via social, blogs, podcasts
- exchanging feedback with founder peers
- reaching out to your network with target profile
- partnerships with similar brands/companiesHacks for sourcing investors:
- be where they already are: founder communities, hackathon & investor-hosted events, industry events, etc.
- create a mechanism for consistent inbound and you won't have to spend as much time on outbound
- find non-dilutive ways to get your brand out there (PR, stonks, pump, many others)Best tools on a budget:
- RT communication: Slack
- Product: Figma
- Website: wordpress or WIX
- Design: Canva
- Creative: Fiverr
- Reporting & Data hub: Notion
- Marketing data: Google analytics
- Product feedback: Loom
- Doc sharing: Docsend (expensive but worth it)
- Calendar mgmt: calendly
- Waitlist mgmt: Kickoff labs, Prefinery or Firebase (DIY)
- TikTok affiliate sourcing: swipehouse
- Video/Audio: Final Cut Pro, Animoto, epidemicsoundLast pieces of advice:
- hire a lawyer with low headcount & a good reputation
- always get a second opinion/quote
- actually read your credit card statement once a month
- maintain a 2:1 ratio of talent recs and interviews
- publish at least one piece of personal content a month (podcasts, articles, blogs, etc... tweets don't count)
- share info about startup life only when asked... you'll be excited to share but don't be annoying
- have a pre-defined date to take a salary and stick to it
- put mental health time on your calendar and don't miss the meeting
TLDR:
- Fail a lot, measure the results
- Turn off the peanut gallery (in bad times AND in good times)
- Relentless personal growth = peak performance
- Cherish listeners & be one yourself
- Give without being asked to
- You don’t need to make a product, to make an impact
- Be kind to yourself
- Have an opinion
- Play this song when you need it
