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Meet Jeffrey

An investor’s stake is his money. Mine is my name.

This is my business. There is no firm behind me to absorb a client that goes wrong, and the market I work in is small enough that word travels fast. If you are not successful, I am not successful, and the next founder who might call me hears about it.

Jeffrey Osborn

I built this model for myself, two decades before it was a category.

2003. A bad economy, and I was out of work. Five lunches with the founder of a small technology company in Los Angeles and still no offer. He finally said it plainly. This is less job than you want, you would be finished by Tuesday morning and bored, and I cannot pay you anything close to what you have been making.

I told him I thought he had just solved the problem. He had the answer, he just could not see it. One day a week, for whatever the company could afford.

A two and a half hour drive every Friday, and four days a week left over. The thing it bought me was time, and time is the thing I sell now.

Forty-plus years, and the size is not the point.

I have carried revenue and P&L inside technology services companies from small firms to global operations, and I have built companies of my own.

What that range taught me is the only reason it is worth mentioning. Whether it is a startup or a global operation, it is a matter of how many zeros are on the back. Everybody has the same problem. We are behind in our numbers, and we are not growing fast enough.

I do not advise from theory. I advise from both sides of the table.

Nobody taught me by handing me the answer.

One of my mentors kept a poster-sized org chart on his wall with every name printed upside down and a thumbtack through the middle. He would turn it over so the point sat at the bottom, with himself underneath all of it.

My job is to make sure each of you is successful. I cannot win unless each of you is winning.

Most people give advice by telling you the answer. Mentors never tell you the answer. They give you the approach. It is like algebra. They show their work.

That is why this is built to end. I am not repaying that by handing founders answers.

Still operating.

I am a co-founder and an active investor in ventures in music, automotive and private aviation, all of them live right now. Which means I am on both sides of this. I am building things, and I am advising people who are building things, and I am running the same play I am asking you to run.

  • Music
  • Automotive
  • Private aviation
Based
Florida Gulf Coast
Industries
Technology services, SaaS, IT and business process outsourcing, managed services and professional services.

If you have a decision in front of you and want a read from someone who has something riding on it, start a conversation.