Startup vs. Startover

It’s been a while since I added a new category to this blog, but it’s time, because I’m entering a new phase in my life. I’ve already done the startup thing. In fact, I’ve done it more than once. But I now realize some of my “startup” attempts were really “startovers” and not “startups”. A startover is when you start up the same business twice. In some ways, I feel as though I’ve started up MWI 200 times–every time I’ve realized I was doing something majorly wrong and changed it. But objectively there have been four primary “startup” moments:

1. December 1999 – Recently married and a college student, I quit my good job and bright future at MyComputer.com (now Omniture, recently acquired by Adobe for $1.8B) and start my freelance web design business under the dba DonLoper.com (yes, the very url of this blog was once the url of my company).

2. August 2000 – I bring on two partners and some employees and change the name to Mindwire Interactive.

3. January 2003 – Mindwire is acquired, my remaining partner goes to work for the acquiring company, and I start MWI, which is ostensibly the same company as Mindwire with a different name and a different set of employees.

4. April 2007 – I start making a profit. How? By letting all full-time employees go and only using contractors, moving from a $5K/month office to a home office, and I start paying myself after four years without a paycheck. On top of all that, I pay off about $90K in debt the first 12 months after making these changes, plus I work 30-40 hours per week instead of 80-90.

Every one of these events has felt like starting a new business from scratch. The two most successful attempts (in terms of profitability) were #1 and #4, wherein I have been the only full time employee, and other employees have been either nonexistent or on contract (right now I have about 15 contractors doing work for me).

For the past two and a half years I’ve been quite content. Scaling down back in 2007 was the right move at the right time…although that’s a bit misleading of me to say it like that, sort of like steering your car off a road and towards a cliff, then turning back towards the road and saying “I felt it was the right time to get back on the road.” But so what, I made a mistake and I corrected it. The point is that now, after these two and a half years, I’m ready to scale back up. But only if I can avoid the mistakes I made previously which resulted in me being buried under a mountain of debt, not being able to take a paycheck, and rarely paying my employees on time. If I’m going to scale back up, I’m going to do it right, and that means there are a few basic rules I’m going to stick to:

1. I take a regular paycheck.

2. I don’t work more than 40 hours in a week.

3. I don’t use any debt.

Wish me luck. More details will be forthcoming, but don’t expect anything drastic. Most likely this is going to be a very slow, deliberate process.