Entrepreneurs on WSO, what you wish you knew before starting?

I know entrepreneurship is extremely difficult. I am aiming to start my own venture in the education industry in few years. I am wondering what do you guys wish you knew before to make the jump?

 

It will take far longer than you think it will to get things really cooking and the entire process leading up to it will stress you to the max. I initially thought 2 years and things would be great, but it took probably around 5 years to hit that point.

You will pick up some real war stories along the way. All entrepreneurs have them, but the one’s who “made it” laugh about it.

Good luck!

 

You absolutely cannot start a business without reading Peter Thiel's "Zero to One." He basically lays out whether or not your business can succeed or not. It's maybe the most amazing book I've ever read. I was so blown away by it that I stopped part of the way through, went back and started taking detailed notes, comparing my start-up idea to his roadmap.

(Of course, we're not talking about small businesses; we're talking about businesses that you hope to sell for "f*ck you" money).

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m_1:
I think it's virtually useless for anyone starting out from a tactical perspective and even strategic.

Well, duh. It's not a book meant to explain business tactics. It's a book that's a gut check for prospective start-up founders as it describes the types of business models that are likely and not likely to make the founders rich. It's a roadmap for businesses that have the potential to succeed at the next level, and if your business idea doesn't fit well into the roadmap for success then it's likely to never be more than a small business.

If you're just looking to have a small business or you're not looking for a 9+ figure exit then yeah, there are other books more suitable.

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Most Helpful

Honestly, the hardest part for me is the fact that the rest of the world can’t see my vision of how my industry (healthcare) should work. That might be on me for lacking sufficient evangelistic qualities.

We started with something that we knew would work from real world observations from a doctor, and it works great clinically and scales well. The biggest problem was/is that healthcare wants to package us in a legacy model that is broken. That is hard to overcome.

It’s taken us 7 years and a ton of great customer validation that our approach works, and people are finally getting onboard. 7 years is a LONG freaking time to live in complete uncertainty.

My biggest takeaways are:

  • it will take MUCH longer than you expect
  • you will have to give your life/savings over to your idea of failure isn’t an option - don’t partner with anyone who won’t do this and expect that you may go to zero anyways (I did)
  • potential early stage investors may not get it, even with some customer traction
  • there will be unexpected problems with co-founders, etc.
  • even when you begin to grow there will still be naysayers
  • when/if you are really breaking out, you live with constant doubt that you are the right person to take it to the next level
  • go in with eyes wide open because I promise that it will be 10x harder than you can imagine. - my life as a BB IB analyst/assoc/VP was chill compared to running a company
 

The stress is more than people expect. It wears you out because it's always there lurking beneath, and then you begin doubting. You don't realize how stable your life is while working for someone else until that stability is long gone.

There are plenty of YouTube videos about entrepreneurship and how hard it is. But even if you prepare yourself for the grind, it's way worse when you're actually in it.

Commit to something that you can see yourself grinding for a minimum of 5 years before giving up. Very few businesses, outside of tech, go anywhere in less than 3-5 years.

 

That its lonely as fuck. I left PE after 2 years and I've been working to buy a business for past 18 months and every transaction I worked on fell apart (about 8, one even had LOI and financing term sheet signed). I stop talking to my finance peers about what I do because I've pivoted so many times in the past year and lots just consider me as some unemployed finance guy that didnt make it.

I basically have nothing to show for in 2017 and 2018 except some very nice CIMs I made to raise capital, terms sheet I received and LOIs I sent out.

The bright side is I have made some entrepreneur friends and almost solely hangout with them as they are the only ones that understand the hustle. My finance peers talk about their bonus, exit ops, comp increase and my entrepreneur friends talk about ideas and how to execute them and tend to have more frugal hobbies.

HOWEVER! Every transaction and meeting I go into I better and more polished and I did get significant traction in the past 4 months. I have been doing consulting on the side for startups raising capital to pay bills until I close my first transaction and one is about to close a $10MM round and I always ask for 25-100 basis points of the raise, so pretty stoked. Also, getting deep in the process to buyout a local telecom co with ~$1MM EBITDA to be financed almost solely with senior debt and seller financing.

Going into 2019 the same as 2017 and 2018. Lots of traction and high hopes. This might be the year my dudes. Just need 1 to close and we set.

keep grinding

 

That hit on one of the biggest concerns regarding working on a startup. Part of me is terrified of the lack of social interaction. I mean, I don't like view of working in a garage to save on rent, and grinding away day in, day out for 2yrs.

How do you deal with the loneliness? Also, how much did you have saved up before going out on your own? How many years have you worked after school before taking the dive? Would you have done it earlier or later, with hindsight?

 
takenotes08:
That its lonely as fuck. I left PE after 2 years and I've been working to buy a business for past 18 months and every transaction I worked on fell apart (about 8, one even had LOI and financing term sheet signed). I stop talking to my finance peers about what I do because I've pivoted so many times in the past year and lots just consider me as some unemployed finance guy that didnt make it.

I basically have nothing to show for in 2017 and 2018 except some very nice CIMs I made to raise capital, terms sheet I received and LOIs I sent out.

Several years ago I, too, attempted to buy some businesses but kept running into the #1 reason businesses are hard to sell--poor financial record keeping. Poor financial records made them essentially impossible to finance with any kind of debt. Was that the main issue you were running into?

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