How to Take Yourself Seriously

Featuring The Entrepreneurship Handbook

How to Take Yourself Seriously

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Why This Episode Exists + Nerdy Stuff Not In The Pod 💡

One of my favorite episodes of all-time.

I wrote it right before I became a dad, and thinking through what type of dad I wanted to be helped me realize that most entrepreneurs don’t think about what type of entrepreneur they want to be. When I ask entrepreneurs what their North Star is or why they’re starting a business in the first place I usually get blank stares as they try to think of some answer that isn’t “I’d like to be rich” or “I think being a founder gives me prestige.”

There’s nothing inherently wrong with either answer, but they won’t help you make decisions. And that’s what a North Star is for - to guide you. If you’re rudderless, you won’t move with intention which means you can’t take yourself seriously. This is a problem. And I’ve been there (the Find Your Lobster story in the pod talks through this).

The pod runs through the idea of your “entrepreneurial self,” a value and decision making engine you’ll build as your startup evolves. We introduce a framework called The Entrepreneurship Handbook that’s become crucial for most of our members.

This handbook has three key components:

  • A Value System

  • A Decision Making System

  • A Reflection System

Doing something on purpose is always better than doing something haphazardly, and how you act as an entrepreneur is no different.

This handbook will help you take yourself and your idea seriously. You deserve that.

And, if you like this stuff and want some books that lean into it a bit:

Pod References

Pod Timestamps:

1:00 Your Entrepreneurial Self
2:35 The Dads
7:00 Byldd
8:04 Why Find Your Lobster Failed
12:40 The Serious Email
14:12 Entrepreneur or Tourist?
15:13 Your Entrepreneurship Handbook
20:30 The End - Implementing

Transcript - Feel Free to Read it Like a Long-form Article:

Today, we’re going to create your entrepreneurial self.

This might sound weird. And it is. Kinda. But, I’ve seen enough of people trying to build startups without one to know that that doesn’t seem to work, so maybe this will. It’s only weird because most people don’t do it for reasons they can’t articulate which, for the record, is the best kind of weird. That’s the weird you should seek out.

The idea of building a new self is pretty top of mind because I’m going to have a baby in the next week. I know this because last week our doctor said she wouldn’t - quote - let us go past the 19th, but since then she’s sent absolutely no follow-up emails or information or appointment times or dates, except for a quick note in the portal that said they might have some time on the 18th so - quote - stay tuned.

There is something weirdly assuring about a doctor treating your wife getting induced to have a baby like they’re scheduling a Zoom happy hour with some high school friends to discuss the white lotus finale, which, for the record, I didn’t watch on Sunday and I’m not sure we’ll sneak it in before the baby so lord help you if you email me a spoiler. Although I’m not sure why you would. But don’t.

Anyway, it’s always funny to think that whatever you do for a living - let’s say you’re project manager at a creative agency, delivering a baby is as routine as onboarding a new client.

Having a kid prompts the question of my life.

What kind of dad do I want to be?

Well… what are the options?

If you’re lucky like I was, you had a dad or a few dads or step dads or some sort of dad in your life growing up. I could certainly be like them. If I’m like my dad my son will hit the lotto.

You and I certainly saw other people’s dads, too. There was the strict dad, the dad that worked all the time, the dad that talked on the phone during soccer games, the dad that coached the soccer games, and the dad that yelled at the refs during soccer games for reasons that had absolutely nothing to do with the refs.

There was the funny dad the young dad the in shape dad the dad that thought he was just another one of his son’s friends and would say inappropriate things that made everyone uncomfortable and the kind dad. There were the dads that remembered your name and all the others that called you bud or pal or sport.

Then, there were the outliers. Memorable dads in a sea of flannel and glasses.

My best friend’s dad hugged me every time he saw me, asked about every member of my family individually, kept a case of snapple in the trunk of his car at the ready for thirsty kids and on multiple occasions took me aside for a stern talk when he decided that I wasn’t playing aggressively enough on the basketball court. “You can be anything you want to be,” he’d tell me, finger hitting me square in the chest, eyes locked on mine “but only if you act like someone who wants it and that is not what you’re acting like.”

When he saw me at his son’s wedding, he teared up. I’m so proud of you both, he sniffled.

For me, a whole bunch of my friends are dads - nearly all of them. I’ve peppered them with questions and gotten all sorts of answers.

My long-winded point is… by the time you become a dad you’ve got a whole lot of context for what a dad can look like. And an idea of what type of Dad you’d like to be.

And still, most people I speak with say they just sort of let stuff happen and react when it does. They rely on instincts and hope. In their words, they “survive.” There’s nothing wrong with this. Humans have been doing this baby thing for quite some time and maybe instincts are the best way. And, it goes without saying, who the hell am I to comment on this before I’ve had a kid.

But, I’ve always found that in my life when you do things on purpose vs leave them to chance or instincts or the holy ghost or whatever, they tend to work out a whole lot better.

So, I’ve started to build out what I’m calling my dad self. Who I’ll be as a Dad. On purpose. I started with some values. The three most important things that I want my kid to have are empathy, resilience, and curiosity. That means I need to do two things. Check in regularly to make sure I’m living by those three characteristics, and check in on what we’re doing with the kid to make sure those three things are landing. I’ve got my north star metric, methods and tactics to get there, and reflection time to readjust the coordinates of the ship along the way.

I’ve told this to parents and they immediately crack up and say things like humans plan and god aka your kid laughs and they know more than I do but hey, even the reminder that those are the priority might be useful when we’re on zero sleep and the kids crying and poor rubes is sulking because she’s not the center of attention anymore.

And when I push and do my customer interview mind tricks on parents we both realize there is a core group of values they’re acting on, but they aren’t explicit and often aren’t conscious. This means, they often aren’t the ones they’d choose.

Separately, a bunch of parents already do this and call them things like Family Core Values. Multiple friends have 3-5 core values and have them on a white board that sits in the kitchen and they mention them every day at dinner and ask how their kids lived up to them that day. This, they say, is what their family is about. Their kids strive for these. Sometimes extra dessert is involved.

So what in the heck does this all have to do with you?

So, so much.

Because while I’m not sure if curating and creating feedback loops around my quote dad self will work, I know for damn sure it works for entrepreneurs.

And entrepreneurs are starting from a way worse spot. You couldn’t help but observe dads in your normal life and absorb, at least passively, what works and what doesn’t.

But what about entrepreneurs? How many entrepreneurs starting a business from scratch have you been around? How many successful and unsuccessful? How many VC backed vs bootstrapped vs service vs physical product? How about entrepreneurs that are great at marketing vs. managing vs fundraising vs. stretching a dollar?

The answer, is probably zero. You’ve probably never been around anyone starting a company from scratch.

And your instincts - as we’ve talked about probably a hundred times at this point - are terrible for entrepreneurship. Entrepreneurship is unnatural. It’s counterintuitive.

So, if you want to take yourself and your idea seriously, you need to build your entrepreneurial self.

If this sounds inauthentic, that couldn’t be further from the truth. The word authentic means to stay true to your values, your personality, your spirit. Regardless of the outside impact, your values, ideals, and actions align.

That won’t happen by accident. So let’s do it on purpose.

After…. a little smooth jazz.

The Real Story of why Find Your Lobster didn’t work … and bike helmets

A good story, or good marketing, or good… really anything… has one thing.

Contrast.

You don’t learn something when someone tells it to you. You learn it when they compare it to something else and you see the clear difference between the two. Context facilitates learning and action.

So here’s a story that pains me a bit to tell, but hopefully helps you out.

The year was 2012. The top songs were Diamonds by Rihanna and Call me Maybe by carly rae jepsen and frankly what a year for music. Lebron James won his first championship, the first hunger games movie came out, and I was starting a company called Find Your Lobster.

But more accurately, I was pivoting.

I’d started a company called 3Degrees in 2011 that let you search and meet your friends’ friends. The goal was to help you take advantage of your network. The job market stunk and I had lots of unemployed business school friends who would send out emails all the time to big groups saying things like “a job opened up at XYZ bank, can you search linkedin or facebook and see if you know anyone there that could get me a warm intro?”

I’d nerded out a bit on Facebook with a friend who worked there and we realized this new thing, Facebook graph, would let outside developers build that type of functionality. So, I raised some money and I did.

3Degrees let you search your friends’ friends on facebook for… anything. Where they lived, worked, activities they liked, etc. The best part was that you could do these searches without anyone being a 3degrees member. You logged in with your facebook account and immediately had access to view millions of profiles. I remember at the time thinking this was maybe a weird privacy thing, so we ended up gating last names for people that weren’t on the app.

So, I might search for a friend of a friend that worked at goldman sachs, see the first names of 25 people that did, then the 2 or 3 friends of mine that knew those people. I could ask them for an intro, and bam.

Also, I hoped people would search for friends of friends who skiid or liked the knicks or … whatever. It’d be the way to meet new people.

We launched and it very much… wasn’t. We got some press and some users and long story short, 99.99% of our searches were for friends’ single friends. People just wanted to see lots of single people then ask their friends for intros to them. There was no tinder, no hinge - this was completely novel. And, people kept their Facebook statuses updated. So, single meant single.

It became obvious immediately we needed to pivot and build a facebook driven mobile dating app. The wave was clearly coming. I remember pitching VCs and getting feedback about how to do both things concurrently - networking and dating - about how to keep the market the biggest it could be. Then, I remember an associate who was maybe 24 piping up at one meeting in front of all of his bosses.

“The data is clearly - clearly- telling you the massive opportunity is dating. Fold this product and build a facebook driven dating app like today. Like, run from this meeting to your developers. Sprint. This is the biggest opportunity we’ve seen all year if your data is right and people in their 20s will use a dating app. You should never think of networking or friendship ever again. Go.”

His bosses were shocked. But he was confident. I looked that guy up a few years ago and he started a company that sold for a few hundred million bucks. Least surprised I think I’ve ever been.

Anyway, I started to pivot over to the dating app which I called Find Your Lobster after that.

A friend of mine ran a development shop that was building mobile apps. I’d grown up with him. He was a contemporary. I reached out and he was excited by the idea. He brought me in and his cofounder, also his wife, talked me through her idea for the product. She’d done some sketches and they were incredible. The cost would be more than I had in the bank. I’d have to raise a bit more.

And, I just… wasn’t sure.

Would this dating thing work? Is it what I wanted to do? If it worked could I handle the liability? Was this really good for people?

Questions, questions, questions. No action. No resolution.

Meanwhile, my friend’s wife and I emailed back and forth for a couple of weeks, strategizing. She’d post suggestions, I’d give some feedback, she’d send some more stuff through. There was no contract. No payment. I was just kind of… swaying. Deciding, I guess.

My friend was cc’d on all the emails but never responded.

Until he did.

I still have the email. We’ll get to why later. It says:

“Guys, let’s not spend any more time going back and forth on this. It’s not a fair use of everyone’s time. Once you get the budget, we’ll draw up a contract. Your next email should either be confirming first payment or confirming that we aren’t working together. Thanks.”

It was a punch in the gut.

Distinction. Clarity. I was wasting people’s time. He was someone who valued his.

We’d been friends since we were 7. But this was not us shooting hoops in the back yard. If he wanted to run a business he wouldn’t have time to work with people like me and he wasn’t willing to sacrifice his business for a moment or two of social awkwardness. And, I respected him more after that email. He was a serious person.

And at the time, I wasn’t. I didn’t know what serious meant. I’d gone to business school and raised some money and built a team and all that… but I wasn’t serious yet.

I responded that I couldn’t work with him because we didn’t yet have the budget and within seconds he’d emailed me intro’ing me to a lower budget agency that would work with me. I was off his plate, clearing it for stuff worthy of his time.

He built that business up, then sold it. Then built another one and sold that. Then another. Now he has an investment firm and charitable trust and floor seats to the nets.

He was serious from the start, and it compounded. That was the difference.

That’s what we need you to have.

Your Entrepreneurial Self

So, what do you do?

First, decide if you’re an entrepreneur or a tourist. Probably 85% of entrepreneurs I meet I categorize in my head as tourists. They like the idea of strolling down the streets of the entrepreneurial world but they aren’t really here to stay. They aren’t committed to it. That’s fine, but then none of this really matters for you.

But if you’re serious about this, if you want this to be your lifes work, you’ve got to take yourself seriously.

That means you need to design your entrepreneurial self. An active representation of what you are and how you’ll act. Because defaulting to your social self will have you in the position I was in with my friend - not ready for what it really takes to be successful.

What you need to do is build what we call your entrepreneurship handbook. A representation of how you’ll act, what you’re after, and methods and tactics to get there. To do it on purpose.

There are a three key components of this.

First, a value system

Second, a decision making system

and third, a reflection system

I’ve built these all into a notion doc - my entrepreneurship handbook - with different tabs. I reference them constantly.

First, your value system. Your stated goals. Why you’re doing this, how you’ll do it, and what type of entrepreneur you’ll be.

There are a few ways to structure this but the end result should be the same. A clear, visual representation of what you’re doing, why, and how. A reminder that’ll eventually become ingrained.

There are three I recommend.

First, an action board. It’s a collage, physical or digital, that has representations of what you desire in life and your startup. I first learned about these from Dr. Tara Swart, a neuroscientist. I’ll link the article.

They’re the why - the people you want to help, the goals you have, visualizations of you getting there. Triggers of what you don’t want. The screenshot of that email from 10 years ago is part of my digital collage. I never want to be the unserious person again.

The secret is bathing in these. Starting your day with them. Tweaking them if they feel off.

Anchor yourself in the things you want to achieve and the tasks that don’t line up will feel more and more like a nuisance - a sap on you as a serious entrepreneur.

Second, are affirmations.

I once spoke with an equipment manager for an NBA team who told me that before every game there’s a line of players waiting to get in front of the mirror and chant their affirmations. What they can do, who they are, what they can be. If it’s good enough for them, it’s good enough for you.

How you act, how you think - it’s all malleable. It’s all a choice. It’s all repetition. The more you do something, the more you’ll be the type of person who acts that way until it’s natural.

Third, are a list of your core values as an entrepreneur. Come up with three or four or five or seven and make sure they really matter.

A quick quote by eleanor roosevelt to drive it home:

“To be mature you have to realize what you value most.

It is extraordinary to discover that comparatively few people reach this level of maturity. They seem never to have paused to consider what has value for them. They spend great effort and sometimes make great sacrifices for values that, fundamentally, meet no real needs of their own. Perhaps they have imbibed the values of their particular profession or job, of their community or their neighbors, of their parents or family.

Not to arrive at a clear understanding of one’s own values is a tragic waste. You have missed the whole point of what life is for.

The next piece of your handbook is your decision making system.

The first part is higher level. This part is actionable.

We’ll start with an example.

Seth Godin has a slide that shows a picture of a group of people riding bicycles together. None of them are wearing helmets. But one girl has a helmet - it’s tethered to her backpack, hanging there, unused.

Humans would rather die in a bike accident than stray from the herd.

So, our decision making system needs to make sure we automatically make the decision to put on our helmet without caring what other people think and without draining willpower.

We need a system for decisions that helps you act the way you want to.

Every time I feel what I now refer to as the bike helmet feeling - when I’m uncomfortable acting a certain way because it pushes against my social norms but I know it’s how I should act - I force myself to do it once. Then, I codify it.

I take the email response that lets the random person asking for 30 minutes to talk about startups know that I can’t help directly, but I value them. And here’s what’ll help them - a video I made a while back about how to get started. And here are other resources. And when they’re ready - apply to Tacklebox.

It takes a ton out of me to write this from scratch. But now, I have 45 different stored responses to requests for my time that I can’t do if I want to reach my goals. I copy and paste.

And now, I have a system. When X happens, I do Y. And it was easy to pass it off to a VA who now handles my emails. As the company grows, the handbook is passed around.

My handbook has the higher level piece - where I want to go and who I want to be - the operational piece of how we make and track certain decisions.

And, the final piece of the puzzle. Accountability.

External accountability is fantastic, but hard to find. We’re building this up at Tacklebox - head to gettacklebox dot com slash rhythm to get some info on that.

But internal, for this, is good enough. Sit down on Sunday and look at what you did the previous week. Match it up with your core values, your action board, what a serious entrepreneur would do. How they’d treat their time.

Did you default to much to your social self? The pleaser? The one afraid to upset anyone in even the smallest way? The one that isn’t actually effective at all in a startup context? How?

How can you change it next week?

What goes in my handbook, in a separate notion tab, is my log. Every night I spend 10 minutes recapping the day. Decisions I made, where the system was pushed, how I can be better.

You know it’s good for you. I know it’s good for you. But you don’t do it. Try the log.

The End

We’ve got a lot of people who listen who aren’t entrepreneurs and this approach really works for you, too.

If you’re spending 7 hours a week managing someone two levels below you who shouldn’t take more than 15 minutes of your day - are you actually helping them? Is this person serious? Are they worth your time? Have they displayed that they are?

If not, how would a serious person in your position treat this? How can you get them off your plate? How can you codify it for people in the future?

Some of this can seem harsh. It can seem inauthentic. It can make you feel a certain way. But separating your social self from your entrepreneurial self is critical because your social self will not be able to build a business. Which means you won’t be able to solve problems and help people and reach your potential.

And, people respect serious people. When my friend sent me that email, I wasn’t mad at him. I was mad at myself. And I changed because I saw how he acted and wanted to be like that.

Creating an entrepreneurship self, crafting it, modeling it, improving it - is hyperunderutilized. Our instincts lead us to terrible startups. Don’t let them creep in where we don’t want them.

-

Well, this is the last podcast I’ll get out before becoming a dad. Hopefully, I’ll be a good dad. But I do know I’ll be a purposeful one.

Warren buffet once said that someone, somewhere is sitting in the shade because years before they planted a tree. The handbook - acting purposeful - about being a dad, an entrepreneur, a person is the seed.

Wish me luck,