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Past startup failures and lessons learnt

This is a bit of a sensitive subject but common among everyone here. Would anyone like to share a story or two? Offer wisdom?

14 Replies

Yuanzheng (James) Wen
2
0
Yuanzheng (James) Wen Entrepreneur
Great topic! I once heard there are many ways to success, but only a few ways to fail. Avoid failures and keep going will eventually getsucceed.
One thing I realized:
  • When starting up with co-founders, it's important to have agreement talking about how to make decision, and what happens if one want to quit. Those topics only gets harder to discuss in the future.
Eric Veal MBA, MSIS, PMP
2
0
Management Consultant, MS in Information Systems, MBA, Project Management Professional, Six Sigma Black Belt Trained
Not sure that I have wisdom but my past startup failures and lessons learnt were to: build a TEAM. Surround yourself with the people and resources that YOU need to get the job done and feel good about doing it. Get others excited. Be willing to be a sales person and advocate! We're all mavericks as entrepreneurs but it takes a team, too. So what I'm trying to do now is build a team and be very communicative about our opportunities and position and how they can help and participate. I'm trying to be clear about the needs that *I* have. I'm trying to lead and do a very social thing far more so than before when I was spending most of my time developing the (software) product. I'm transitioning from engineer to sales person and team leader.
Justin P. Williams
1
0
Justin P. Williams Entrepreneur
Digital Marketer and Data Analyst
Briefly ... I forgot about handling taxes. Sounds silly, but it turned out to be a huge problem. Find someone who knows what they're doing taxwise, setup a system, and plan ahead.
Lilia Tovbin
1
0
Lilia Tovbin Entrepreneur
Co-founder at BigMailer.io
Here are some lessons and considerations:

1. Have a co-founder agreement clearly outlining responsibilities and what happens to shares if somebody isn't performing as agreed. There are many great posts on this topic on answers.onstartups.com

2. Have critical expertise or knowledge for the product/market represented on the co-founding team. First time founders have to learn many things and not being able to understand your customer needs or marketplace dynamics can be very costly.

3. It helps to be motivated by reasons other than making money. The passion for a product or the journey itself will help keep going when things don't work out as expected.

4. If you have a significant other, it helps to have their buy-in and support, or even better - interest and willingness to help out with their expertise.
Lilia Tovbin
0
0
Lilia Tovbin Entrepreneur
Co-founder at BigMailer.io
Agree with Justin, think about accounting upfront and organize your data from day 1. I would suggest to setup your accounts (checking, credit card, paypal) with Outright and add categories/notes on ongoing basis so it's not a huge burden come tax season.
Douglas Tarr
4
0
Douglas Tarr Entrepreneur • Advisor
Entrepreneur and Software Architect
I spent 4 or 5 months last year building a website (now defunct) called undo.io. It was meant to be a hybrid of a todolist, notepad, calendar and twitter.

I did no customer development. I just wanted to build it for myself. :)

I was previously a co-founder at a successful startup in Seattle. I had a secret feeling that there was something special about me, and my next project would just magically succeed.

I came from a Microsoft background, but decided to learn Ruby on Rails to do it. Everyone kept telling me I could code things faster and better if I went FOSS.

It took me twice as long as I thought to build it. It was hard to use. It was unclear what it was for.

I didn't even really think about a business model ( I just thought - "... probably advertising" ;) )

I worked a lot, worked through vacations. My back went out. I gained 10 pounds.

Eventually I realized that there was no viable business and it was just a personal project, I shut it down and didn't do anything useful for 2 months.

Then I pulled my entire family up, moved back to California, and started again on new business.

What I think I did right
I learned some important technical skills - Ruby on Rails, Linux, SOLR, Vim, Heroku, and a few other pieces of that stack.

I didn't break the bank to do it. I kept working at another job and that made my home life less stressful.

I killed it when I realized there was nothing left for me to do with it.

I connected with a lot of really smart and supportive people.

Didn't raise money at all, which gave me more freedom to turn it off when it wasn't working.

What I Think I Learned
I am an incurable entrepreneur.

People are willing to help if you ask.

I appreciate people who are willing to try something (anything) new. I try to acknowledge, congratulate, and encourage any effort to start something up now.

I learned that productivity software as a category can be radioactive to many investors . :)

I learned that every venture is a mix of successes and failures.
John Rodley
1
0
John Rodley Entrepreneur
CTO & co-founder at Twiage
+1 on all these mistakes, especially Dougs. Classics every one. I'm sure I'll revisit many of them personally.

Here are some later stage mistakes:
  • Too much space, too soon with too long a commitment. Founders fall in love with the idea of space. We did and ended up with lousy space and the property owner on the cap table.
  • The 83b. This was an almost-mistake, thank Bieber. I have a long blog post coming up on this as soon as taxes are done.
  • Hiring a skill rather than a person. In my last, successful, venture I hired twice for skills and got burnt both times. I hired for the same skill three times in a row because it seemed esoteric and difficult and finally threw up my hands and gave the job to a guy we already had who knew nothing about it. He promptly killed it, in his spare time between killing the two other jobs we had him doing.

Justin P. Williams
0
0
Justin P. Williams Entrepreneur
Digital Marketer and Data Analyst
+1 to hiring a skill rather than a person. I hired someone who had the skill set, but two weeks in just started complaining about all the things I should be doing for him. Waste of time.
Kevin Adler
3
0
Kevin Adler Entrepreneur • Advisor
Founder/CEO, Miracle Messages
In a nutshell, we let our mission interfere with our progress.

Before pivoting into inthis, I ran alumn.us, which was meant to be a kickstarter-like platform for under-served schools. We had such a passion for helping public schools and community colleges fundraise from alumni that we neglected to realize how difficult it was to a.) learn how to build a robust engagement platform while b.) working with schools that had little to no fundraising infrastructure or experience.

A much better course would have been to start with elite private schools that do a ton of fundraising, and put those processes online and streamline them. We learned a lot through our fundraising campaigns at a local SF school, helping them fund a computer lab in the process. But we could have moved a lot faster, and realized the bigger opportunity of bridging the gap between online and offline, which we're pursuing at inthis.

Wrote about this in full recently: http://social.yourstory.in/2013/02/kevin-f-adlers-baby-steps-to-success-with-alumn-us/
John Rodley
0
0
John Rodley Entrepreneur
CTO & co-founder at Twiage
I love your full writeup Kevin.I especially like the advice you give to aspiring entrepreneurs experiencing failure ;)

I did a less entertaining version of that here:http://pointyhairedstartup.com/2013/01/07/mistakes-ive-made-a-few/
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