50+ Common mistakes first-time founders make -- and what to do to instead to extend your runway, improve your product and retain the team

3-Part Series

Originally published in March through October 2023

Please note: All examples of start-ups/products/services are fictional; any resemblance is coincidental. 

This will be a 3-part series covering the most common VC-facing, customer-facing, and company-internal mistakes first-time founders make.

I’ve made – if not all – then some of these mistakes the first time around I started my consulting business, and have shared the lessons learned publicly at a number of conferences over the years – and am still making mistakes and learning from them. Having mentored, advised, and/or consulted for over 100+ start-ups, I see similar themes come up again and again – because (most likely) we haven’t had training on how to run a profitable business, and are all doing things the hard way. :) We’re all still learning!

When one of my friends had a call for an executive panel that’s willing to share common mistakes that first-time founders make, I originally thought I only had 2-3 mistakes to share, but it’s since turned into this 3-part series of blog posts. 

Please note: This series is not meant to be a criticism of anyone, but is a reflection of making difficult decisions which all have trade-offs; founders that are not first-time founders also make these mistakes (!). As such, this blog post is a list of things to watch out for to help you manage expectations and make better decisions as you navigate your business journey, with all its ups and downs. This is especially true for (early-stage) start-ups, who have short runways and need to (understandably) make the best of it. 

Please note: This series is not meant to be a criticism of anyone (I've made all/most of these!) and should not be treated as a checklist of things you're doing wrong now. We all make mistakes! Instead, this is a list to review from time to time, to make sure that everything is set up as best as possible given the information you have at the time -- and what challenges and opportunities to watch out for, in the short- and long-term.

Without further ado, here are some of my lessons learned the hard way – to guide you on the DOs and DONTs of running your business and how to try to make the best of it. Hopefully, it helps you become a better leader and run a more profitable business!

Part 1: VC-Facing Mistakes

Please see this blog post on to help you better understand the most common VC-facing pitfalls first-time founders make -- and advice for strategies to try instead.

Part 2: Customer-Facing Mistakes

Please see this page for advice on customer-facing mistakes to avoid -- and what to try instead.

Part 3: Company-Internals Mistakes

Please see this blog post for what to consider to avoid the most common company-internal mistakes to avoid -- and what to try instead.

Parting Advice

Everyone will have an opinion on everything -- because everything is a trade-off! Don’t be surprised if you get 100 opinions from 50 people on each of these topics (!). At the end of the day, it’s your call because you’re the CEO. You got this!

There’s a story (or two) behind each of these (!); I’m always happy to meet other leaders in the field and swap stories and lessons learned.

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