Opening Bid Unfiltered is available on Apple Podcasts, Spotify, YouTube, or wherever you get your podcasts.
Before building a billion-dollar cybersecurity company, Okta (OKTA) CEO Todd McKinnon had to convince one person first—his wife. At Salesforce’s (CRM) Dreamforce, McKinnon spoke with Yahoo Finance’s Brian Sozzi on Opening Bid Unfiltered about how a PowerPoint presentation helped him get her blessing to quit his job and launch Okta. He reveals what that moment taught him about risk, conviction, and betting on yourself.
Listen on your favorite podcast platform or watch on our website for full episodes of Opening Bid Unfiltered.
This post was written by Langston Sessoms, producer for Opening Bid Unfiltered.
Video Transcript
00:00 Speaker A
Tell me about, and this is something I've never asked you about. Tell me about the PowerPoint you presented to your wife when you started Okta.
00:04 Speaker B
Yeah. Well, when I started Okta, I was working at Salesforce, had this great job, and got really excited about doing something new on my own. And my wife is very, uh, she's very a little bit risk-averse. And at the time, we had a six-month old baby, and she was pretty skeptical about me leaving my job. So when I came home and told her I was leaving, she reacted very vociferously in a negative way.
00:32 Speaker B
Um there may have been some expletives dropped there.
00:36 Speaker A
Fair enough.
00:37 Speaker B
Um and so I had to make her a presentation to argue my case. And if you look back at it now, it's pretty funny because um, a lot of the things it's very precient, right? It says, oh, cloud is going to be the next transition, there's going to be massive companies made in this time period, etc, etc. But it also was, you know, not so precient because I thought the biggest, most successful Okta would ever be would be maybe, you know, worth $100 million. So, I was got some things right and I got some things wrong. and luckily she was super supportive and
01:14 Speaker A
Have you had to update the PowerPoint since or it just sits somewhere in a file?
01:20 Speaker B
It sits it sits for posterity. As a as a as a reminder of uh, even if you get things right about the future, you're all should be humble because you never know everything that's going to happen.
01:34 Speaker A
Is that one of the tips I guess you would give to an entrepreneur if they're watching this? Share things with your partner? Like is that bring them into the process because look, 16 years of what growing Okta, nothing's in a straight line.
01:52 Speaker B
I think yeah, I think the the the thing that I notice with entrepreneurs is that they just the ability to embrace the unknown and to to kind of roll with uh you don't know what's going to happen and you can try as hard as you want, but you have to embrace uncertainty because you don't know what's going to happen. You have to get a lot of things right in terms of hard work and strategy, but a lot of it is is up for chance. There's timing, there's risks you haven't foreseen. and just you know, releasing that sense of control and going for it is the hardest thing to do. It was the hardest thing for me to do and that's the advice I gave to entrepreneurs is like you're not going to be able to control all the factors. You just have to give in and release into this uncertainty and unknown and charge for it as fast as you can and try to make something happen.
View Comments
Okta began after the CEO made a PowerPoint for his wife
Published 3 weeks ago
Oct 15, 2025 at 12:00 PM
Negative
Auto