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Why Thinking Big is Terrible Advice for New Founders

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, waitress, 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 into 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 it 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 responsibilities.

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 to 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 cheatsheets.

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 at 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.

This article was originated from my blog where I write about building stuff, #BuildingInPublic, etc.

🥦🥦 My question to you is: if you're not a first-time founder, do you think you manage these obstacles much better now with experience?

  1. 3

    Certainly wish I could go back to 2011 and tell myself this.

    During my PhD my co-founder and I built a complex algorithm to identify "breaking news before it breaks" on Twitter. It worked (kinda) but it was an immense undertaking with little focus.

    Now I much prefer to start small, niche hard and start by addressing the problem rather than starting with the product (i.e. our new detection algorithm). It's the oldest cliche in the start-up book, but it's a cliche for a reason :)

    1. 1

      We've all been there ;)

  2. 3

    @kevon Thanks for doing this detailed post!

    One of the best key takeaways I got from your post was -
    "find your lane, and stay in your lane"

    Couldn't agree more with you. I had always been relatively good at designing and spent couple of years working as illustrator. I believe that the very knowledge of the industry helped me thrive at building my own agency successfully.

    QQ for you -
    How did you manage to created the last box at the end of your post? Like what markdown function did you use to create it? It seems like a great way to ask questions from readers.

    1. 1

      Hello Siddhita! I'm glad you resonated with what I had gone through myself. I had been "seeking ideas" in diff places for too long haha!

      Oh I randomly stumbled upon that, use >> to start your line and it will turn into that nice little box :) Super useful here indeed!

      1. 1

        Thanks for the answer! Yeah, it's great to catch readers into important tips!

  3. 2

    Kevon - spot on advise - and all the best for Toasty!

    1. 1

      Thanks Meera! I stopped working on Toasty since Oct 2020. The growth wasn't hitting my expectation and I didn't want to take more investor's money so decided it was time to call it a day. Now I'm more focused on writing while discovering an itching problem in the writing space :)!

  4. 2

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

    Agreed 100%...that said, it doesn't mean you can't start a company to help those people, but it's going to be much harder.

    Businesses tend to have the best chance of success when the founder can stick with it for years. It's really hard to do that if you spend the first year making no money in the business because you don't understand your customers.

    1. 4

      “It takes 10 years to build a career in anything.” - naval

  5. 1

    yes, to answer your question. of course! as a serial founder, i've learned a ton... and i'm applying those learnings into the current project! it's great.

  6. 1

    @kevon great post!

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

    It seems a great place to start for aspiring founders would be to 'scratch their own itch' no? Since they are more likely to understand the space?

    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.

    This is reminds me of the idea 'get paid to learn the business'. You're an employee for a certain amount of time, learning the business inside and out, once you have depth of understanding, you branch out.

    Also I think the number one pitfall of aspiring founders is they fall in love with their own idea. It's almost like pivoting or admitting it doesn't quite solve a valuable problem hurts the ego too much so they start building regardless.

    Why do you think new founders avoid this focus on solving problems? Is it because it's often painful and emotionally difficult?

    1. 2

      I hope I can give you a good answer!

      Mainly because we, human, are idea generators. We love coming up with solutions, it creates that adrenaline that we need. I notice that founders are super super excited when they first think of an idea, and then as they find out more, their excitement decreases.

      Coming up with an idea is the easy part, making it a viable business is the hard part. And most people don't find connections between the two until they learn from failing.

      And yes, admitting your idea sucks and pivoting are damn hard for most because they think their reputation/face are on the line, when actually that is the noblest thing to do and the most attractive to others like investors or partners.

      1. 2

        Thanks for the thoughtful reply! Yes as a new aspiring founder, I have seen this exact phenomenon with myself. After I read your post I also read Courtland's How to brainstorm business ideas post and it made me realize I have been jumping straight to the idea generation before working on the 'identifying the problem', 'how will i reach customers' phase. I fall in love with idea generation, but I'm doing the whole process backwards its seems. Good learning lesson though.

        1. 1

          We've all done that :)!

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