I have always had a side hustle.

Even back in the early 2000s, when I worked in a global ad agency, I would take calls with my personal clients in the beautiful sun from the second-floor outdoor patio the agency would brag about during onboarding. I billed $50K on top of my full-time job one year from side hustle ad work. But that's a different story.

I used to attend lots of tech networking events and conferences in SF. If you're not aware, there are usually two or three networking events a night, nearly any day of the week.

One day, I was having drinks afterword with a good friend and I was complaining how all these events kinda suck, and I could do a better job. I spun some story about what I thought would make an awesome events series and conference. At the end of my tall tale, my friend said, "You should do it, and I know people at this co-working space who might let you use it for an event."

He called my bluff.

But never wanting to back down from a challenge, I agreed to meet them and pitch my idea.

I put together some slides and shared them with the team that managed the space. They loved it and agreed to give me the space.

No mailing list.

No brand.

No website.

I had nothing but my big mouth. Now, I had to have an event and get speakers and attendees.

I needed speakers first.

I built a prospecting list on LinkedIn of interesting people from hip startups who I thought would be great speakers and started doing cold outreach via email to them. After a week, I had two speakers. I got two more in the next week.

Now, I needed attendees.

The event was free, so I put it on every local mailing list and app that listed free events in SF. I also set up a page on EventBrite to manage tickets and promote it through that platform. I hoped for the best. It worked. We got 100 signups and 50 attendees. I couldn't believe it.

10 events later, we were the talk of the town.

We hosted these events once a month in SF, and one event we did on design was a smashing success. We were completely oversold by triple the venue capacity. I thought to myself that this topic had legs. Let's go big.

Organizing a 150-person conference was hard.

I went back to the venue that hosted us for free and asked if I could use the space for a full day to host a mini conference, and they said yes! OMG, now I had to pull this off. We used all the same techniques, cold emailing speakers to fill the roster with excellent people. Great content drove ticket sales. Getting speakers wasn't that hard. We had a reputation, and people liked working with us. But selling 200 tickets (you must oversell to fill the venue) was a slog.

To sell the tickets took a relentless sales effort on our mailing list, on social media, and through placements on event websites and newsletters. 90% of the tickets sold were through discount codes so we could track the source. We even gave all the speakers their codes so we could track that as well.

It was a huge effort, a sold-out show.

We used the same approach and did an even bigger event the following year in a larger venue, that one hit $100K.

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