What's the biggest mistake you've made as a founder?

Richard Fang
103 replies
This sounds silly but when I launched my first startup 5 years ago, we didn't put in a vesting schedule 😅 Wanted to see what others have done but also things we know to avoid in the future!


Two biggest mistakes - insufficient problem hypothesis validation and poor mentor-mentee values fit.
Richard Fang
@gogloballakshmi What happened with your mentor - mentee part?
@richardfliu we just didn't see eye to eye in terms of execution.. My strategy was different from theirs and the communication style was a mismatch when discussing disagreements. Of course I understand this on postmortem.. I did not have this clarity when I was caught up in action.
Prateek Mathur
@gogloballakshmi Was this an advisor presented to you by your investors?
@prateek_mathur mentors and advisors are not the same... I was bootstrapped, never took investor money... startups are about communities too..
Artem Smirnov
I should have hired a mentor who would force me to think more clearly about our startup and hold me accountable. Or join a preacceleration program. I think we would grow much faster.
@artem_smirnov A mentor is to facilitate, IMO nothing should be force especially for a founder.. What I see is you wanted someone to communicate with, so a matching communication style will help with achieving goals..
Andrea Brice
@artem_smirnov I've done that, am doing that. I'm having to rethink because I'm self-funding and this is expensive expensive. But she helped me re-pivot and if she holds me accountable (which is a big deal) - which she has - then I need to maybe just eat it and live with it. I was literally re-thinking the investment this morning. It's painful because "intangibles" like "clarifies", "calms", "synthesizes" is not lines of code or bugs killed, newsletters written, or instagram posts.
Adrian Topka
I think the ones which cost me the most time and cash were: 1. didn't make market/idea validation with the clients, before start the work. (I just had the assumptions) 2. Lack of a mentor. but it's hard to avoid that when you are a 1st-time founder. You want to launch asap, you think you have the best idea in the world, and so on.. :D
Not releasing until all planned features are completed. For https://watermark.ink I built a complete visual editor for custom templates and most my users hated it and said its confusing.. I thought its not worth wasting time in customer support, so sadly I have to completely remove templates feature (this feature took 50% of total dev time). Must have gone to market early and got this feedback.
Justin Hunter
Biggest mistake I made was misreading the market and having tunnel vision on a future customer base that didn’t exist rather than focusing on the customer base that did exist and was happily using the product already.
Ismael Fi
My biggest mistake is actually trying to Avoid mistakes by applying a specific framework. (lean ... ) Mistakes might be very different depends on products type. Sometimes trying to release as soon as possible can get you troubles but sometimes you have to release asap and go further to reach potential customers. Not Trying AB testing outbound vs inbound marketing for software based product.
Richard Fang
@ifinnaoui Some good points! I think finding the fine line between releasing early and taking too long comes with experience haha
Eddie H.
Not enough focus on marketing.
Eivind Håverstad
Two biggest mistakes - Thinking about opportunities too long before execution. If executing, waiting too long with talking to potential customers in an early stage phase.
Sven "Locomotive"
Not communicating enough - still working on that
Wilhelm Rahn
Underestimating how expensive less-than-ideal product-market fit is when dealing with government institutions.
al3sha is Salt
I once started a tech company at the beginning of the DotCom ... bust.
Dean Ayer
@al3sha I did that, the customers kept asking "Are you going to go out of business?" and we were saying "No, we just launched!" ....and it was a SaaS about 10 years early but its still running today, 20 years later LOL.
Jake Desjarlais
Giving away too much of the company for early help.
Richard Fang
@seeenjake Could I ask what you did specifically here?
Maria Zacharia
Waiting for around 6 months for US registration when we could have started off with an Indian Company.
Emma Phượng Nguyễn
Co-founder/ Important people breakup. When I know somebody for years and think that we can be business partners, it turns out that it is all illusion. I would be brutally honest to myself as a solo founder rather having fancy people on board.
Richard Fang
@emmanguyen Yeah I acutally ran into this problem with one of my friends. Realised we're really great as friends but terrible as a co-founder partner (she's more of a corporat person).
Emma Phượng Nguyễn
@richardfliu Startup game is starting from scratch. Not simply copy & paste solution from one place and put it to another market. The corp/ big org is well-designed process - Doing well in those does not mean you will thrive in startup.
Jake Strouse
Procrastinating. It has always been a huge issue for me, and has lead to some great ideas never being pursued.
Devanand Premkumar
@influxes I know how you feel. Been there, its quite a pain and I have lost quite a lot because of that alone.
@influxes i feel that means you weren't really excited about them. perhaps led you to something better: you have passion + good idea.
Jake Strouse
@angelina_magr I was excited for them to be a reality. But I was not excited about the pains of building them. So I procrastinated.
@influxes not excited enough then? :P
@influxes i think that's the best! save your energy to something even better. You can "meh." the rest of them.
Not validating idea!
Andrew Thompson
OH GOD, so many mistakes. Overpaying employees and not negotiating influencer contracts.
HHi Sofa
Hi, Usually I never comment on blogs but your article is so convincing that I never stop myself to say something about it. You’re doing a great job.Keep it up. Have A Nice Day!! Thanks
didn't make market validation before putting too much time.