Startup Cabin Blog

Mistakes I made in my 1st Startup: A collection

Posted by Steve Ferris on 07 December 2014


Experience is the best teacher. While some lessons are exciting and empowering, there are others that we wish we could do without. These hard lessons are a part of everybody's life, and even more so for those who venture into business for the first time.

I knew there had to be tons of lessons that were learned the hard way, and that those who learned them would be eager to share with others so they could learn with less pain. And the responses poured in. Try to avoid these mistakes.

I asked the community on "What was the biggest mistake you made in your 1st startup?" And this is what they had to say.

Don't delay tough desicions

"Didn't fire the non-performing co-founder fast enough. It was toxic to the morale." Victor Huangex-Trader, CEO of a small software company

No competion is a big red flag

Assuming that because nobody else was doing it, I'd have a corner on the market. Wrong! LOL-Catharine Symblème

It always takes longer than you think

"In short, not being realistic about the amount of time everything would take. If it's your first startup, you don't necessarily have a good idea about how long you'll need to devote to development etc., especially if you're a non-technical founder. We definitely didn't. A while ago I heard another startup founder give a talk, and he said something that really struck me: "Things will take three times as long, and cost three times as much as you think they will". I've now passed that quote onto so many other people it's untrue!" - Ria Blagburnco-founder - emble


Build a good company culture

"Its funny, because I made so many mistakes as a founder, that I can't even pinpoint one mistake! However, if I can think of the biggest mistake, it would be forgoing building culture. 

I know every investor, entrepreneur, advisor, talks about culture (I know mine did) but frankly, I did not care at the time. I was so focused on short term goals that I didn't see the ROI of culture. 

Looking back, culture is the single most important thing that a startup has. Think about it like this - your culture is the reason why people actually come to work every day. Why do people stay at a company? It's not because they get paid $500,000 a year, but because they love the work they do, feel challenged every day, feel wanted, etc. 

ESPECIALLY if you are building a startup, how can you expect to recruit those people that are getting paid $500,000 at a tech startup to come work for equity?-Chirag KulkarniSerial Entrepreneur, and Advisor. CEO of C&M Group"


Customer development before product development

The biggest mistake I made was selling something people needed badly but didn't want to pay for.

I was running a training company. We developed a training methodology that was fairly revolutionary.

The evidence of it's effectiveness was overwhelmingly on our side. And I built a thoughtleadership platform:

  • I wrote a book that was named an award-winning finalist for a national book award.
  • Our book release campaign netted strong endorsements from over 20 industry leaders and trade organizations.
  • Our newsletter, visibly better care, had a list of several thousand and won an award for publication excellence.
  • I presented to Hospitals and health care organizations as a podium speaker.
  • We wrote three whitepapers. The whitepapers were picked up and redistributed by a quality assurance organization for the Centers for Medicare and Medicaid Services (the largest insurer in the United States).
  • And I was a one time or regular contributor to a number of medical publications.
  • We held training for a number of top hospitals in our region and around the country as well as nursing schools. 

But I list all of the stuff above because the important part is that despite the evidence and positive reviews, we could not get traction.

Finally, one of my contacts at a hospital pulled me aside and said, "Tim, you are not going to be able to make this go. If I were to put all my nurses through your training, it would cost me $40,000 in labor costs, not to mention the cost of your training. And that's just to put them through once."

The net is that there's a big market for Patient Satisfaction surveys and reporting, and probably even speaking on patient satisfaction. But there isn't a demand for the training which is what my firm was set up to do.
About 6 months ago, one of my contacts from a big account called me asking about my book and asking why I was doing digital marketing instead of this training. He said the home health care industry was in the throes of looking for just this kind of information. I asked him how much his firm would pay us to train all his home care workers. He said, "Tim, I could get you 5 platform speeches next month. And one would hire you. Nobody can afford this kind of training."

I now recommend customer development before product development. And I bang the drum for Steve Blank and his Lean Start Up philosophy. Because I've lived the downside of pouring years of your life and stacks of your money into a product that people need badly...and just don't want to pay for."

Tim DawesStarted two businesses. Working for a microcompany now.

Trust your gut, and act quickly

I stuck around for much longer than I should have.  The CEO was burning through cash and everything was falling apart.  I let my loyalty override my better judgement and we ended up homeless for brief period of time.  
It took a long time to recover from that.... Naturally, I did not learn the first time and ended up in a very similar situation years later with an almost identical outcome. - Chapley WatsonRuby Dev, Entrepreneur

Ouch! Some of these really sting. I want to thank all of those who contributed, and I hope you were able to take something valuable away from these mistakes, because those were expensive!
Want to share your 1st startup mistake with us? Tell us in the comments. This post will grow over time and could include your experience.

Topics: Marketing Strategy

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