You got to recognize the problem, want to solve it, and have conviction and want to win, and off you go. I can call people up now and say, 'You want to do it the hard way or the easy way?'
God, I would hate to get that call from you.
Cool. All right. Well, this is my first go at a live podcast, so I don't know what's going to happen, but we both have a sufficient number of microphones on that this will be good.
Yeah. And I feel rude not facing the audience, but because it's a podcast, the audience is out there and my camera is there. If you're back there, don't think I'm rude. I'm doing what we do on podcast. And I'm going to leave the second we're done because I have Nancy and Paul Pelosi sitting with Gail and I on the floor of the Warrior Game tonight. And if you know Nancy Pelosi, she is always prompt and has told me to be prompt.
We will not be late. And we're gonna get to that type of thing as one of sort of your superpowers. So everybody knows who you are, but as I was thinking about this conversation in this audience, we have a bunch of seed investors here in various forms of the job and various stages in their career and you are sort of the person who is the kind of archetype of angel investing. You've been sort of almost embarrassingly successful investing in like Stripe and LinkedIn and Facebook and Google and PayPal and Airbnb and Pinterest and almost more than it's like reasonable to name. And so what I kind of wanted to do was to try to open up how you've made that happen and have you kind of look back over the decades of your investing and try to glean what an investor in 2026 can learn from you and your success and try to take for themselves. I think the place I wanted to start was like if you could try to kind of give your own narrative of your own career starting from when you first got into investing and like what played out over time just to sort of ground us in like what your sort of professional life has been all about.
Well, I think it all starts with age and seniority. And speaking of age and seniority, your mom is here and I want to recognize her.
My mom is young. There's no age.
Hey, I view myself as young, too. But I want to recognize that mom is here. And we had a good time at Sam's 40th. And this is why I bring up age because I've been through every technology cycle starting with semiconductors which is where I started my career. I did not like school. I couldn't wait to get the hell out of school. So I left San Jose State and the next Monday I started work at National Semiconductor in the Santa Clara Valley when most of Santa Clara Valley was fruit orchards and an occasional semiconductor factory. So I went, you know, I've been through the semiconductor phase which kind of gave way to the computer phase. It gave way to the software phase and then into the 90s with the internet boom and then today the AI boom. The AI boom is bigger than all of those combined. I swear to God. It's hard to fathom. It's hard to keep up with. But I think we all have that problem because there's so much change happening at once. Even in the internet boom, you could kind of keep track of things. You know, Netscape was Mission Central. Netscape's the one that allowed you access to all of this corpus of information on the web. And from that, you know, we got the internet boom. So, I was fortunate to go work at National Semiconductor. A few people at National went off and started a company called Altos Computer. They asked me to join. This is when the microcomputers were disrupting DEC, Data General, Prime, Wang. Does anybody remember these names? But this little Altos computer was upending them. So it's, you know, technology is all about disrupting. So we were disrupting the many computer companies. And I love it because I interviewed sitting on the floor. There were no desks, nothing. I was the head of sales on Walsh Road in Santa Clara, literally like five blocks from National Semiconductor. And because I was the sales guy and justifiably so, technology companies are engineer driven. And our engineering CEO Dave Jackson, who had more charisma, you know, this Brit just exuded charisma and helped me close anything that was hard to sell. You're the sales guy. You sit next to the coffee machine next to the factory, which is just fine with me because I was traveling a lot anyway. So we built Altos. Altos went public. We had a very successful IPO.
I'm guessing, but our stock went public at 21. We had our closing dinner at Club 21 in New York. I told my wife when I left, this is not a normal business trip. We're going public the end of this week. We're going to be what we call wealthy. And she said, you are so full of it. And she happened to go to the bank the day we went public and I sold some stock and the guy goes, 'This is like the biggest deposit we've ever had.' And she called me up in New York and said, 'What in the hell is going on? You've done something bad.' I said, 'No, no, we just went public.'
Like, you need more IPOs. What? She's like, 'You need more IPOs.'
Yeah. So, I ran Altos. But we ran into bumpy water because along came, you know, if you don't disrupt yourself you will be disrupted. That's one of my benchmark sayings. If you don't disrupt yourself you will be disrupted. And we were complacent. We had a great IPO, you know, we thought we were king of the hill. And along came this little thing called the PC connected to the Ethernet which replaced these multi-user systems. So we had to sell the company to Acer, the value of our real estate. And I told the Acer when I was selling them, this real estate's worth a hundred million so it doesn't really matter what you pay for anything else. And it's on Trimble Road, that real estate's now probably worth a half a billion. So then I was out of a job and Don Valentine was our lead board member, everyone knows Don Valentine the founder of Sequoia Capital. He came on the board very soon, was the only investor, came on the road show with us. And Don, he has two sons and a daughter. Like any father with, you know, I'm going to see where that daughter goes. He picked Altos out of his whole portfolio because he liked our culture. And another thing that a founder has to do is build the culture. Some companies have bad culture. They allow philandering, etc., etc. That's not a good culture. Those people are not role models. I'm just not going to name them.
We can name a couple if you want, but think about...
But culture is important and he knew, you know, that we built a great culture and we had all these young kids. Dave Jackson's kids worked there. It was a really cool place. And our motto was play hard, work hard. There was alcohol, but it was on Friday night and then Monday everyone back to work. So Don says to me, 'What the hell are you going to do?' And I said, 'Let me tell you, I don't like managing people.' I found that out because close to a thousand people and you just become an HR director in my opinion. Some people like managing and God bless those people. We need managers. And Don said, 'Well, if you don't like managing people, why don't you just come hang out at my place? Come to board meetings and watch me give founders advice. You've already been a founder, so you know what it's like. And why don't you become an angel investor?' So I went to board meetings with Don and in the middle of the first board meeting I was spellbound because he was giving this founder advice that I knew I could give the founder. So I just started investing in startups on my own and that led to becoming institutional, etc.
Was there a moment in your early angel investing journey where something important happened like was there a seminal investment that changed everything for you? Was it a slow build? Like how did you go from just, you know, sitting in that first board meeting to like getting the traction that you got?
We made a bunch of investments and a lot of them failed. Our very first angel investment I ever made was a company called Natural Language Incorporated, Berkeley, California. Natural language sounds like AI. Yeah. My first investment ever. I'm not exaggerating now. I dredged this up after the AI boom. Who would care five years ago. But it was run by two guys, John Manfredelli and Ginsburg. I forget his first name, that says my synapses are working right now. Way too early for AI. So guess what we did? We had like all good founders, let's go find a home for ourselves. We went up to Microsoft and Bill Gates already was all over AI and he wanted the team. So, we brought the team up. I didn't tell him, but we were out of payroll. And he goes, 'I'm going to buy the company.' I said, 'You got to buy it today.' And he goes, 'Hey, I'm going to buy the company.' I said, 'No, we're going to do it today because otherwise you'll go sell to somebody else.' He got really furious. And down came the guy who now owns the Giants who is the general counsel because I said you can't leave until we sign the deal. And he goes, 'Well, how about it became a game? How about if I bring down my general counsel and he doesn't leave until the deal's done so I can go run my company?' I said, 'That's good.' Manfredelli still works at Microsoft. But the investment that kind of got the clock ticking and things going was Ask Jeeves. Ben Rosen and I, Ben Rosen was a Morgan Stanley star analyst who loved and covered Altos Computer. Morgan Stanley always, Altos was always a buy. We all loved each other. He went and started Rosen, Seven Rosen Partners. Compaq and Lotus were his wins. He retired from there when I was getting started and he said, 'Ron, let's go do this together.' Just investing our own money together. Nothing formal. But Ben sourced Ask Jeeves, not me. The guy on the East Coast sourced Ask Jeeves in Berkeley. And him and LJ7, they each had a private plane. This is years ago, but they each had a private plane. I would pick him up at the airport and we'd go, we wouldn't have a board meeting. We'd have a build the company meeting and the three of us with the founders of Ask Jeeves built that company together and it was so much fun. The funnest part was in the car, me much younger than the two of them, chauffeuring these two who were pretty old at the time, and the things they would say and the stories they would tell. And it was all about we're going to make Ask Jeeves a huge company.
