The mental game of startups
My friend Jess wrote a post about learning mistakes from other founders so you don’t have to make them yourself. The first lesson he teaches their startups? Know thyself.
Self-awareness allows you to build solid foundations in your personal life, which directly impacts the business you build.
This was one of the most important lessons we taught in our pre-accelerator program, but I don’t see a lot of entrepreneurs doing this.
I developed an in-depth process to help our founders become more self-aware which allowed them to create solid foundations to build a business.
This process is something every founder should go through before they decide to jump into their business full-time.
The program
We ran 13-week program where you would come in to learn how to build a startup (and the mistakes to avoid), and then apply the knowledge to your startup idea.
Founders would dig into the problem they wanted to solve, come up with idea hypotheses, treat the idea like a scientific experiment and prove that people actually wanted it, and put together a solid pitch to get investment.
NOTE: This program is not running anymore as the content is now online and we do more bespoke programs with founders.
It was intense. We ran 8 cohorts (3 at any given time) and we learned a lot.
There were key points in the program where people would get stuck, but the halfway mark (Week 6 or 7) was particularly sticky. This was the point when we would teach Facebook ads.
There were two problems:
- A huge learning curve.
The Facebook ads platform is complex and hard to learn. It’s especially difficult if you don’t have an experimental mindset. Some founders would try one set of ads and if they didn’t work, they saw it as a failure. - An emotional barrier.
After digging deeper, we discovered the problem was much more emotional than we had realised. And it was all based on fear.
Many founders put their self-worth in their idea. It was their once-in-a-lifetime BILLION dollar idea. But up until this point, they had only told their mum and close friends who had given them unconditional support. Rarely had given them real feedback on the idea.
They were terrified of the truth. When your self-worth is tied to an idea, and someone criticizes the idea, it feels like they’re criticizing you. And when you’re at the mercy of an anonymous troll who writes up a nasty comment, it’s soul-crushing.
In some cases, founders didn’t tell anyone about their idea and kept it like a dirty little secret.
When you tell someone, you become more accountable and they’ll check in to see how it’s moving along. And what if you fail? What if no one wants the idea you think will change the world? That’s soul-crushing as well.
So as the founders were learning the ads platform, they had this emotional blocker that prevented them from fully learning or from actually launching the ads.
With emotions running high, I wanted people to learn more about themselves, uncover the reason they wanted to do this idea or run a business, and help them build solid foundations to actually do it.
Startups are so intense that it’s tough to succeed without solid foundations. If your personal life is a mess, your startup will likely be a mess.
So when founders came into the program, they thought they were getting their idea investment ready. Little did they know…I had other plans for them (muahaha).
1-on-1 (therapy) sessions
I spend most of my free time learning about psychology and human behaviour, which means I have a whole heap of resources and exercises ready to drop on you at any moment.
My community manager role quickly turned into a psychologist role.
Along with weekly learning workshops, founders had occasional 1-on-1 sessions with our CEO Adrian where they got specific feedback on their startup idea. And then they had 1-on-1 sessions with me to focus on the emotional side of building a startup.
My goal was to have every person become more self-aware.
Sometimes this meant people pushing themselves harder than they ever have before. And sometimes this meant people learning that entrepreneurship wasn’t for them. And sometimes this meant they realised they didn’t care about the tribe or the problem they were solving. All of these were wins for us.
I’ll walk you through the journey I brought them on.
Get to know yourself
Before founders started the program, I had each person take two personality tests.
The purpose of these was for the person to learn more about themselves, but it also gives me insight into how to work with them.
This test explores four facets of our personality (you can take the test here). If I did this again I would use The Big Five as I think it gives a more in-depth analysis of our personality, including virtues (things you’re great at) and faults (areas to improve).
The two most prevalent personality types in our community were ENFP and ENFJ.
NOTE: This doesn’t mean those types are more likely to be entrepreneurs as those types (particularly extroverted) may be more attracted to a group education program.
80% of the founders we worked with were extroverts (E).
70% of the founders thought about the world intuitively (N). This means they love talking about ideas and trust their gut when making decisions as opposed to their counterparts (S) who focus prefer details and concrete information.
70% of founders made decisions based on how they feel or how the decision will make other people feel (F).
The point of this was not to put people in a box but to have them understand why they do the things they do and the challenges that might present with people who have opposing characteristics. A common example of this is the communication gap between the big vision focused entrepreneur and the factually minded developer.
This framework on habits and motivation (internal versus external) was created by Gretchen Rubin. This was important for me to know in communicating and setting challenges for the person.
Each week founders had “homework” or “startup work” to complete and I tailored my language to their tendency.
Upholder — You are internally and externally motivated.
If you put a task on your to-do list or calendar, it gets done. You are easily motivated but sometimes you do unnecessary tasks without question because it’s on your list, not because it actually needs to be done.
This person loved challenges and always completed all homework (often ahead of time). Some of these people didn’t even need challenges because their lives were already so put together. In those cases, we stuck with something small, like flossing every day.
“Complete this homework before you come in next week.”
“This is the challenge you must complete by this date.”
Questioner — You are internally motivated. You can be externally motivated but you need a reason and it must make sense to you.
You resist being told what to do and you ask a lot of questions so a request can make sense to you.
“If you don’t complete the homework you won’t be able to participate in next week’s workshop and get specific feedback on your idea.”
“This challenge is important to you because it will improve your life by x,y, z.”
Obliger — You are externally motivated. You prefer having someone else set deadlines, hold you accountable, or attending group classes.
People who are obligers tend to force themselves to be internally motivated, which often results in failure and disappointment. If you recognize this you can set yourself up for success by finding an external motivator.
“I need you to complete this homework by next week so we can all help each other in a group activity.”
“I want you to complete this challenge because it’s important to your family. I’ll check on you next week to see how it’s going.”
Rebel — You resist internal or external motivations. You hate sticking to a routine or schedule and prefer to do things as it feels right for you. Rebels love choice and unconventionality.
This person often did the homework (at the pace they wanted) but never wrote it down for feedback. They did what they wanted to do and when they wanted to do it.
“If you choose to do the homework this week, it will benefit you in x, y, z ways.”
“If you want you can try this challenge, it might benefit you in x, y, z ways.”
Rebels often do the opposite of what they’re told. So if you tell them they can’t do something, they prove you wrong. This was a fun tactic to play with.
So in an email to a cohort I might have said something like this to appeal to all tendencies:
“Next week we’re doing this activity because of x, y, z benefits. If you choose to complete the homework you can get feedback on your own idea and the rest of the group can benefit from your insights.”
Build solid foundations
In the first check-in, we did a Wellness Wheel to gauge where the founder was at in six areas of wellness: physical, emotional, intellectual, social, financial, and spiritual.
I had a list of 50 questions I would guide them through and they’d fill in a pie piece of the wellness wheel for how much they agreed with that statement. When all the pie pieces had been coloured in, we were able to see where the gaps were.
It was common for people to have at least one area that needed work.
Then we’d reflect together.
How do you feel about where you’re at?
Was anything a surprise?
Where do you see those gaps the most and how does it impact you?
Next, we’d set a challenge to work on the gaps.
Challenges could range from flossing your teeth every morning or having a difficult conversation about money with your partner. One area many people wanted to work on was how much alcohol they drank, whether it was bringing their three glass nightcap down to one glass, or to reduce how often they used it as a social lubricant.
Most importantly the challenge needed to be achievable. So when someone told me they wanted to quit drinking, we’d dig into why it was important to them and make it realistic. To completely cut out drinking was too big of a behaviour change so most people would cut their consumption in half to start. Their habit tendency also determined the challenge requirements.
We’d reconvene in 3–4 weeks to reflect on how the challenge went and how they felt.
If they followed through with it, we’d figure out how we could take it to the next level or move on to another challenge.
If they weren’t able to complete it, we’d reflect on why and alter it based on what they struggled with.
I’d also send resources for them to work on based on the gaps in their wellness wheel or something they were excited about learning.
So if their gap was in the financial section, I would recommend Rich Dad, Poor Dad or I Will Teach You To Be Rich. Or a simple exercise of tracking how they spend their money (without restriction).
During this process, some founders realised their values or goals didn’t line up with being a startup founder. They didn’t want the stress or lifestyle of building a huge business. Maybe they started a small business or used the knowledge they learned to get a promotion in their current job.
This realisation was a win for us. Not everyone is cut out for entrepreneurship and we were glad they figured this out before spending too much time or money on their idea.
These exercises help build solid foundations and the right conditions for a business. If your personal life is falling apart in one or more areas, you’ll be distracted and never be able to give the business your full attention.
If your partner doesn’t support what you’re doing…
If you don’t have a lot of friends and feel lonely a lot…
If you are dealing with a physical or mental health problem…
All of these things become magnified when you build a business. Take care of yourself first. Business (and changing the world…) comes second.
This story is published in The Startup, Medium’s largest entrepreneurship publication followed by +396,714 people.
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