Series of mistakes, at a decision point, and possibly a rant.

Six years ago I started a new company to provide services locally.  I had started with a partner but he died 3 months after we started and I was left as a solopreneur.  Fortunately, after 4 years it was at a really good state and I was comfortable with it.  Since my partner died, I designed the company to be a one-man show and could have just gone into maintenance/happy mode.

Then I came up with another startup idea.  And with my success in company 1, I was full of confidence.

This one was much more global in scope (software company) and could help a lot of people while making a lot of money.  I spent a year just doing market research while maintaining my first company.  I tried looking for a co-founder for company 2 without much luck.  Granted, I was keeping it to my circle of people I trust who all have family responsibilities.  Got some help, but no actual commitment, and then they eventually had to get full-time jobs.

Regardless, I was still enthusiastic, had started talking to some people (friends) about investment who were also enthusiastic (albeit non-commital until more was complete), and almost all of the intended customer base across the province that I talked to liked the idea with many saying they needed it right away.  I got a (very) small grant based on the idea, and placed in a pitch competition as well.  People liked the idea.

So in year 2, I hired a development team (minimal size) for company 2, and a support staff person for company 1 to allow me time to spend on company 2.

In retrospect (now in year 3), the hire for company 1 was still a good idea.  I actually had to double my server capacity in December (which was costly) for new customers and I still get recurring revenue which has paid for part of company 2 but not close to being able to pay for everything.

Company 2 has become a money pit and a giant ball of stress.  I was hoping investors would have committed earlier and ended up re-mortgaging my house and emptying one of my investment accounts so there isn’t much credit left, just to get to an MVP.

The last couple of months have really worn me down.  Mainly worry about money and wondering if I have what it takes to do what is necessary for company 2 to build while also maintaining company 1 (that I thought I could step further away from) and not ignoring my family.  Sleep does come quickly at night, but for short periods before my worries take over my dreams and get me thinking again.

The odd thing is that even when things have started to get better for the business lately, at least in terms of possibilities, I still can’t get excited about it.  I’ve had some good meetings with possible customers and know what needs to be done to get them to pay.  It’s a 3-month plan, which the investors like and are now willing to make an investment, but only to cover 3 months of development (also expensive).  I have meetings set up with another related company that wants to integrate.  And I found another company that is working on something similar that I am hoping to talk to about possible partnership.  All good things, but I’m still not excited.  More than anything I feel afraid to lose other people’s money if I mentally crash.

All of the good things are coming to a head in the next week.  Part of me wants to just quit before I bring more people into it.  It will be costly, but I figure I can recover in 10 years (I’m mid 40’s with 2 tweens) and spend more time with family.  Another part of me (and oddly my wife) thinks I should at least see the next few months through and take another chance.

Right now I feel guilty when I’m working on company 2 as I’m not working on company 1 or family (those 2 balanced nicely).  I also feel guilty when I’m not working on company 2 as I’m letting a big idea go.  On top of that, there is an opportunity for company 1 to buy out a competitor, if I hadn’t sunk all my money into company 2, which makes me feel guilty about that.

Anyways, here are the mistakes I’ve realized I made:

  1. I should have spent more time looking for a co-founder in order to not spend money on development.
  2. I should have waited until I had commitments from investors before hiring developers and spending all my money.
  3. As I was doing my market research, I should have gotten written letters of intent from potential customers who were interested, which may have made investment easier.
  4. At this stage in my life, I should have let myself be happy as a successful local entrepreneur without getting caught up in the excitement of a new idea (I have been accused of being easily bored).
  5. Trying to start a new company while also maintaining another running company was a bad bad idea.  Especially without someone in place to completely run Company 1.

So there we have it.  Still a whirlwind of emotions.  More so than I remember in the first company (even after my partner died).  I’ve read the advice that people have to take care of themselves first, but that small part of me that sees the big potential doesn’t want to give up and call this thing (and me) a failure.  I’d like to get back to happy again.

Rant over.


  • Don’t even worry about the prospect of losing your investor’s money. They’re not children, they know they’re taking a big risk. That’s why they stand to gain if everything works out.

    If you’re going through a whirlwind of emotions you should trust your wife.

  • Am in a similar situation. Single founder, existing product, clients lining up on the door for the new one.

    However, programmers make constant mistakes and cannot get it done. It becomes a nightmare.

  • Maybe you could ask yourself: is the fact, that you‘re afraid to do the next step, emotionally related to the death of your co-founder of company 1? If so, maybe you hold yourself back in order not to protect yourself from burnout?

    Take your time to consider your thoughts. Which emotions do they relate with?

    Wish you and your family and companies the best!

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