Why thinking big is bad for you

I almost always say yes if an aspiring founder asks me for advice.

When I was first starting out building products and businesses, I had always wanted this kind of feedback and pointers from someone just ahead of me. And, of course, it was very hard to find.

Last week, I caught up with Ed. I met him in person in 2020 after we got connected on LinkedIn. He told me he had a couple of ideas floating in his head and would love to catch up.

On the call, we hopped from one idea to another. Of course, I tried my best to share any failures, advice, or random thoughts I had.

After the call, I reflected and noticed there are things aspiring founders have in common:

1. You mostly talk about your solutions. You rarely start by addressing a problem.

2. You are not sure where to start. The ideal next step in your head is usually quite a leap.

These are not just extremely hard, there is no good way to prevent yourself from struggling through them. I learned my way as I was stuck for so many years.

I want to see if I can break down the Why and lessen the pain you have to go through if you have an idea and want to know where to go with it.

Why founders don't talk about problems enough

Your conversations with people are always a pitch about your solution.

How you envision the future to be, how your ideas will reshape people's behavior and make their lives better, etc.

These are signs that you don't have a clear understanding of the space.

When you haven't worked in the restaurant business, it is easy for you to talk about how you want to build a 24/7 automated kitchen where there is no waitress. You can even talk about how you'll be providing healthy meal options because that's the trend.

However, if someone has been in the business for years. They usually start by saying what problems most restaurants are facing and how they can solve them.

The truth is when you haven't been in the business, you don't know what people (the stakeholders like owners, kitchen staff, waitresses, and customers) are thinking, what motivates them, what bothers them, etc.

I learned my hard lessons when I was running Toasty. Because of COVID-19, we were forced to adapt our technology to the video meeting space. None of us had experience working with video conferencing technology. We also didn't know anything about virtual events, communities, or meetings.

I tried to overcome this by arranging dozens of user interviews to get the full picture of the space. And I can tell you that unless you're a veteran entrepreneur, user interviews can be full of traps. They can rarely give you enough understanding to tackle problems in a new space.

Over the years, I've found that the easiest way to overcome this is to "find your lane, and stay in your lane". If you've been in the Education space, find problems in there to solve.

This is why the popular entrepreneur stories are always about someone like Peter who went to work for an ice-cream shop for 2 years and then opened his own shop and expanded to 20 cities.

Find problems by immersing yourself in the space for a long time.

Why founders' ideal next step is always quite a leap

You have an idea and you're thinking about finding a co-founder or landing funding. Then you sit on this idea for 6 months and nothing has happened yet.

Whose fault?

Media should take some responsibility.

When you go to any technology media platform, it is always about big fundraising stories. How someone has an idea, finds a co-founder, raises millions of dollars, and grows so fast to raise another round of funding.

These stories are over-glorified.

What about the promising alternative of bootstrapping a business that is profitable? Nope, no one is interested because it is not sexy.

But what bootstrapping does is train founders to be scrappy problem solvers, like in video games. The player has to resolve the puzzle at this level to unlock the next level. You have no extra resources, so you're forced to figure it out yourself. Well, unless you go on forums to find cheat sheets.

The venture path trains founders on an entirely different skillset: pitching ideas instead of validating problems, raising money from investors instead of earning money from customers, and building a team to outsource work instead of figuring out what moves the needles.

Media creates this illusion that the venture path is the best path to entrepreneurship.

I also learned this the hard way. I raised angel funding at Toasty and I jumped into building a team full of engineers and designers. We didn't have a good understanding of the video meeting space, yet we started building the product immediately. My time was spent on managing people and expectations, which meant I was training myself on the wrong skills in such early days.

There are definitely entrepreneurs who are great at going down this venture path. But those stories, skills, and learnings are rarely applicable to an aspiring founder who is just starting out.

Ironically, a video game could be a better training ground to know how to systematically resolve puzzles and build a business.

Advice to the 13 years old me

I started tinkering with the Internet when I was 13. I made websites that attracted thousands of visitors and a forum that had 10,000+ members.

I loved building and serving people online, yet I gave it all up when I went to boarding school.

Thinking back, it was one of the biggest regrets of my life.

I was obsessed with the Internet and I was having a lot of fun. I should have continued to create and put out products. If only had I focused on what I knew best at that moment, and worked on the next small thing that could grow my projects, it would have been the best entrepreneurship lessons back in 2005.

This is also my advice to you, the aspiring founder.

The only way to learn is by starting and doing things relentlessly. You should go deep into a space and don't worry about making big leaps. Be laser-focused on solving the puzzles in front of you, and over time, the 1% daily improvement will get you to where you want.