Past startup failures and lessons learnt


April 5th, 2013

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

Douglas Tarr Entrepreneur and Software Architect

April 5th, 2013

I spent 4 or 5 months last year building a website (now defunct) called  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.

Kevin Adler

April 5th, 2013

In a nutshell, we let our mission interfere with our progress.

Before pivoting into inthis, I ran, 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:

Yuanzheng Wen

April 5th, 2013

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 get succeed.
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 PMP Management Consultant, MS in Information Systems, MBA, Project Management Professional, Six Sigma Black Belt Trained

April 5th, 2013

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 Williams Digital Marketer and Data Analyst

April 5th, 2013

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 Co-founder at

April 5th, 2013

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

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.

John Rodley Technical co-founder with exits

April 5th, 2013

+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.

Michael Borowski Analytical Entrepreneur Interested in Online Stuff

March 11th, 2017

When I first started E-Commerce:

Originally I used wix, but I really recommend not building it through them because there checkout system for cards/ paypal is a major major pain. I ended up finally using (not .com, I do not host services through WordPress, just use their CMS) for all the rest of my sites, there is a million addons for everything you want to do and its open source (free) unlike . I Buy all my URL's/ Domains through and host all my websites on (Might switch from Hostgator soon, they've had some down times during terrible times). Hostgator has a great portal with one click install for WordPress themes. There are thousands of Free WordPress themes that you only have to change minor things in with he WordPress editor when you are hosting it, there are also themes you can buy an they range from $20-150, I have bought one for 60 bucks and I'd say it is semi worth it but I'd first fool around with a free one because its only minor changes with the paid ones.

E-Commerce cash to bank transactions, I've used a few but found that Stripe + TD Bank have returned most positively to work with, why so specific on the bank? I went to several banks when deciding to do E-Commerce sales and my main question was what are their rates for online transactions from an E-Commerce platform to deposit to their bank, many banks answered a % till 100 , or 500 transactions and then a flat fee of .0**, and I found that TD's are free! So if you're wasting money on transferring money to yourself I'd switch.

Lilia Tovbin Co-founder at

April 5th, 2013

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. 

Justin Williams Digital Marketer and Data Analyst

April 5th, 2013

+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.