The biggest lesson from working in tech?

You host these legendary meetups on the San Francisco group on Reddit. What was the inspiration for starting them?

Technically, as for the actual legendary meetups, I must give credit to serendipity and the people of San Francisco. But, to answer your question…

I have been going to the House of Shields regularly for about 15 years now. It is my favorite bar for myriad reasons, one of which is history. 121 years old, original wood, original tile, still has the tunnel running under New Montgomery Street between what was a speakeasy at the time and the Palace Hotel, so the dignitaries and VIPs such as Warren G Harding, 29th President of the United States, could come over for a nip… and perhaps the company of a lady, unbeknownst to Mrs. Harding. Or was it?

So, as you can see, I love my bar. And am dear friends with all the bartenders at this point. I am also a huge fan of Reddit. And one night, while at the bar with my dear friend Hamilton Byrne Cline, I decided to posit the statement and question to the San Francisco subreddit (r/sanfrancisco) "What’s your favorite bar, and why? Mine in comments." And in the comments of this Reddit post, I mentioned that if you come by and see me, I’ll buy you a drink.

Though the post received a good response, nobody actually took us up on the offer to come to get a drink. So Hamilton and I were curious: If we literally say in the title of the post “Come meet up and we’ll buy you a drink,” would people actually come?

So I posted a picture of myself, and said in the title “I’m here, come say hello and I’ll buy your first drink…”. We waited and one person showed up. Peg - The first person to ever show up at the meetup, and one of my favorites of all time. She's still a regular. Because of her, I posted a 2nd time.

The next time a few more people came. Over time, some became regulars, and then they became friends. But they were also my support system because as this little social popup started to grow into a Reddit phenomenon, it became hard to carry on so many conversations. So my regulars would engage with the newcomers, which is how the “networking” of the meetup grew from this organically.

So, in short… I had a fun idea to try something on Reddit, Peg showed up, fast forward to the 1 year anniversary and about 100+ people showed up to celebrate this beautifully organic, marvelous community-based event. COVID killed it for 460 days... but now we're back!

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What surprised you the most while hosting the meetups?

When the CEO of Reddit, Steve Huffman, came to the meetup. He was there for a couple of hours just hanging out with the rest of the attendees, having beers, before I ever realized who he was. Hamilton knew right away, but he also knew not to tell me, because he knows I’m a fucking fan-boy and would probably make a fool of myself. That’s the best pal for you, right there.

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What excites you about your job?  

What I love best about my job is I teach people about what we do at Okta. I’m a teacher, consultant, showman… I love to teach. So I have a great time doing it. I also love my company and coworkers, and the culture and values of our executives model. That’s sometimes hard to find in a company, but should always be considered when looking for a career move.

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What was the biggest risk you’ve taken in your life?

I’d say moving on from a company that I was really comfortable with, could do my job on cruise control, still even had fun, but knew I was not being challenged. But not just “oh, this is not challenging,” but instead

recognizing the repercussions of being comfortable and complacent.

That I could be left behind technically and my skill set would become obsolete. So for me, it was making the decision after being with a company for 15+ years that it was time to move on to other opportunities that may prove to be more rewarding professionally and personally.

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What’s the biggest lesson you’ve learned from working in tech?

Biggest lesson is getting to know people. So much of my success has been because of the opportunities I’ve had because of the people I know.

And I hope that others can say the same of me and the opportunities I may have brought to them via the connection we’ve made. And it’s not only about “the people you know NOW.” It’s also very much about the people you can potentially know.

And to know more people, it’s going to take some effort. This Reddit meetup provides an opportunity to apply that effort but in an environment that may be less stressful. I mean, it’s a bar. There are libations, although that is not required for the meetup.

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