WEBVTT - Sukhinder Singh Cassidy on Entrepreneurship (Podcast) 0:00:02.040 --> 0:00:07.160 This is Mesters in Business with Very Renaults on Bloomberg Radio. 0:00:08.200 --> 0:00:11.440 This week, on the podcast, I have an extra special guest. 0:00:11.840 --> 0:00:15.960 Her name is Kenderson Cassidy and she has had a 0:00:16.079 --> 0:00:21.560 fascinating career in technology, starting as an analyst in the 0:00:21.600 --> 0:00:27.680 investment banking group at Merrill Lynch before going west to 0:00:27.840 --> 0:00:30.800 join a company that ends up getting purchased by Amazon, 0:00:30.920 --> 0:00:34.280 and she stays at Amazon for a while before leaving 0:00:34.920 --> 0:00:37.920 UH to join another startup that ends up doing well. 0:00:38.040 --> 0:00:42.519 She eventually takes a couple of roles at Google Google 0:00:42.560 --> 0:00:45.600 Maps and then running a couple of other projects Google 0:00:45.840 --> 0:00:50.880 International Commerce, and from there ends up launching a couple 0:00:50.880 --> 0:00:54.160 of more startups, all of which that have done very 0:00:54.360 --> 0:00:59.640 very well. UH. She talks about the process of risk 0:00:59.680 --> 0:01:04.319 taking and decision making and why you can't think about 0:01:04.400 --> 0:01:08.640 the risk reward calculus in terms of one big win 0:01:08.760 --> 0:01:11.200 or lose choice. You have to think about a series 0:01:11.800 --> 0:01:16.480 of smaller incremental steps that all involve risk and eventually 0:01:16.640 --> 0:01:20.560 determine the path you take. It's a good framework for 0:01:20.680 --> 0:01:26.400 both technology and finance. I thought this conversation was quite fascinating, 0:01:26.760 --> 0:01:28.720 and I found her book to be intriguing as well. 0:01:28.840 --> 0:01:34.720 Choose Possibility with no further ado My conversation with Sekenderson Cassidy. 0:01:36.720 --> 0:01:41.840 This is mesters in Business with Very Renaults on Bloomberg Radio. 0:01:43.000 --> 0:01:46.880 My special guest this week is Sekenderson Cassidy. She is 0:01:46.920 --> 0:01:51.720 a technology executive and serial entrepreneur. Previously she was president 0:01:52.040 --> 0:01:56.920 of stub Hub. Her new book is Choose Possibility, Take risks, 0:01:56.960 --> 0:02:02.200 and Thrive even when you fail. Sekenderson Cassidy, Welcome to Bloomberg. 0:02:02.520 --> 0:02:04.800 Thank you so much for having me excited to be here. 0:02:05.040 --> 0:02:08.320 So let's talk about your career, which is really so 0:02:08.400 --> 0:02:13.760 interesting it it covers everything from UH finance and investing 0:02:13.840 --> 0:02:18.640 banking to technology. UM, let's begin at the beginning. You 0:02:18.720 --> 0:02:22.200 started at Merrill Lynch in the early nineties, a great 0:02:22.240 --> 0:02:26.280 time to start in investment banking. What motivated that decision 0:02:26.720 --> 0:02:30.280 to go into finance? Um, well, a couple of things. 0:02:30.360 --> 0:02:33.800 Number One, I'd say the most more intelligent reason was 0:02:33.840 --> 0:02:37.120 because I wanted to a base in financial literacy and 0:02:37.120 --> 0:02:39.639 financial analysis, which I thought would be great for any 0:02:39.680 --> 0:02:42.720 career I had. And then the more emotional reason. Honestly, 0:02:43.240 --> 0:02:46.640 I was at a top undergraduate business school in Canada 0:02:46.720 --> 0:02:49.080 and all my friends were doing it, because like, well, 0:02:49.080 --> 0:02:51.920 if they're doing it, I should be doing to. So 0:02:51.960 --> 0:02:54.359 in some ways I call I call it a copycat goal. 0:02:54.680 --> 0:02:56.240 I'm sure there are many ways I could have gotten 0:02:56.240 --> 0:02:59.720 financial literacy, but I was bound and determined to keep 0:02:59.720 --> 0:03:03.239 pay with my rather competitive colleagues to get a job 0:03:03.240 --> 0:03:06.000 on Wall Street. So you you head to New York, 0:03:06.040 --> 0:03:09.920 you started Merrill Lynch. Any formative experiences stay with you 0:03:10.040 --> 0:03:14.280 years later? What do you most remember from that era? Well, 0:03:14.320 --> 0:03:17.800 the first is, honestly, just to struggle to get the job, 0:03:18.000 --> 0:03:20.520 believe it or not. And uh and I say that 0:03:20.560 --> 0:03:23.200 to people because often we look back on the careers 0:03:23.240 --> 0:03:25.240 of you know, others and think they're they look so 0:03:25.280 --> 0:03:28.000 pretty from the outside, but from the inside. It took 0:03:28.000 --> 0:03:30.840 me a good year plus to get that job. I 0:03:30.880 --> 0:03:33.720 was rejected by number of banks. Meryl didn't even come 0:03:33.720 --> 0:03:36.640 to candidate or recruit, and they offered me one of 0:03:36.640 --> 0:03:40.080 those polite informational letters that said something like, if you're 0:03:40.120 --> 0:03:41.840 ever in New York City, would be happy to give 0:03:41.880 --> 0:03:46.120 you fifteen a fifteen minute informational interview. And I remember 0:03:46.400 --> 0:03:48.400 saying to my father, I'm like, well, what is't that? 0:03:48.480 --> 0:03:50.240 They just rejected me and he said, well, why don't 0:03:50.280 --> 0:03:52.360 you take a train ticket and head down to New York. 0:03:52.880 --> 0:03:55.480 You never know? And um, and I was at the 0:03:55.560 --> 0:03:57.520 end of my rope. I've been searching for a job 0:03:57.560 --> 0:03:59.840 for over a year, I said, as I said, determined 0:03:59.840 --> 0:04:02.680 to at this job and not successful. And I took 0:04:02.680 --> 0:04:05.080 that train ride in fifteen minutes turned into a three 0:04:05.080 --> 0:04:11.000 hour interview, and then they accelerated me to the final process. Uh, which, 0:04:11.040 --> 0:04:13.400 if you know, for investment banks, is very competitive. I 0:04:13.440 --> 0:04:15.600 came down on a weekend and competed with all the 0:04:15.640 --> 0:04:18.560 sort of IVY League American kids who had been through 0:04:18.640 --> 0:04:21.880 rounds of interviews. Undoubtedly, um and I got the job. 0:04:22.040 --> 0:04:25.640 So it was a pretty sweet, pretty sweet success after 0:04:25.880 --> 0:04:27.360 a year and a half of trying. But it was 0:04:27.480 --> 0:04:31.000 very formative for me because it really informed and you know, 0:04:31.040 --> 0:04:33.719 I guess my view of how often you have to 0:04:33.760 --> 0:04:35.800 just keep choosing in order to get to the goal. 0:04:35.880 --> 0:04:39.480 You want keep keep banging away. So so, what what 0:04:39.520 --> 0:04:42.039 did you do for Meryl when you when you get 0:04:42.080 --> 0:04:44.440 the job? What was it that they had you do? 0:04:44.520 --> 0:04:47.760 What were your responsibilities and what was the job like? Well, 0:04:47.800 --> 0:04:50.240 and I think this is probably the second former of 0:04:50.320 --> 0:04:52.840 experience I had at meryll Um. So my role with 0:04:52.920 --> 0:04:56.440 the financial analyst, anybody who maybe has studied finance know 0:04:56.600 --> 0:04:58.960 that that's really a job where you create pitch books, 0:05:00.040 --> 0:05:02.960 books with facts and details about different industries. I was 0:05:03.000 --> 0:05:06.440 in the financial services industry group I was assigned to, 0:05:07.040 --> 0:05:08.960 and you really you know, create those books or what's 0:05:09.000 --> 0:05:11.599 called managing directors who go out and pitch you know, 0:05:11.760 --> 0:05:15.200 large companies on using their services M and A services, I, 0:05:15.279 --> 0:05:17.960 p O services, what have you. And so the average 0:05:18.000 --> 0:05:21.120 analysts is spending you know, days and nights softened through 0:05:21.160 --> 0:05:24.120 the night, toiling to create these perfect pitch books. So 0:05:24.160 --> 0:05:26.760 I certainly had that experience, but I ended up working 0:05:26.800 --> 0:05:31.360 for a pretty eclectic young managing director called Henry Michaels. 0:05:31.400 --> 0:05:34.600 And Henry was you know, as detail orange as they 0:05:34.600 --> 0:05:39.000 could get, type smoking, you know, definitely capable of driving 0:05:39.000 --> 0:05:41.880 others crazy. But he took a really deep and early 0:05:41.920 --> 0:05:44.360 interest in just teaching me about, believe it or not, 0:05:44.400 --> 0:05:47.280 the savings and loan industry. And I think he found 0:05:47.360 --> 0:05:50.920 me to be maybe uh rap students. And I freely 0:05:50.960 --> 0:05:53.080 admit after taking a year to get that job, I 0:05:53.160 --> 0:05:56.400 was just bound and determined to be successful um at it. 0:05:56.560 --> 0:05:59.720 So I was you know, very inquisitive, very curious, and 0:05:59.760 --> 0:06:02.360 as result, Henry kept staffing me and putting me, I 0:06:02.400 --> 0:06:06.080 would say, on jobs with increasing responsibility. And so pretty 0:06:06.080 --> 0:06:08.680 early on I was going to meetings with CEO, so 0:06:08.880 --> 0:06:10.680 he would he would set up and let me attend. 0:06:10.800 --> 0:06:12.919 Of course I was carrying the pitch books, but that 0:06:12.960 --> 0:06:15.640 didn't really matter to me. The exposure did um and 0:06:15.680 --> 0:06:17.279 as a result I ended up working on an I 0:06:17.360 --> 0:06:20.280 p O early the Long Islands, I think bank. Henry 0:06:20.360 --> 0:06:22.760 kept giving me more and more responsibility, and in my 0:06:22.800 --> 0:06:25.560 second year Merrill sent me to London, which was unusual 0:06:25.600 --> 0:06:28.000 as well to send something that early, and I got 0:06:28.000 --> 0:06:31.200 to go, you know, work on banking in the you know, 0:06:31.240 --> 0:06:34.680 in the European banking industry, and had just an amazing experience. 0:06:34.720 --> 0:06:37.919 So I gave Henry Michael's a lot of credit. Henry 0:06:37.960 --> 0:06:41.600 definitely skipped a bunch of players to teach me, and I, 0:06:41.680 --> 0:06:44.120 as I said, maybe my best contribution, as I was 0:06:44.160 --> 0:06:46.880 a wrapped student. But the result was, you know, an 0:06:46.880 --> 0:06:49.160 experience where I got a lot of exposure so very 0:06:49.200 --> 0:06:53.520 quickly to kind of senior executives. Really really interesting. I 0:06:53.640 --> 0:06:58.240 have a specific recollection of the Long Island Savings Bank 0:06:58.320 --> 0:07:01.640 going I p O in the early I want to say, 0:07:01.640 --> 0:07:06.040 mid nineties, and eventually I was the analyst, and eventually 0:07:06.040 --> 0:07:09.480 it got acquired, and then that company got acquired and 0:07:09.600 --> 0:07:13.240 at a certain point you just lose track. But this 0:07:13.360 --> 0:07:17.280 leads to an obvious question. All of your background is 0:07:17.400 --> 0:07:21.760 finance related. How did you transition to tech and what 0:07:21.920 --> 0:07:25.400 made you decide to leave the East Coast and the 0:07:25.440 --> 0:07:28.920 world of finance for the West Coast, which has more 0:07:28.960 --> 0:07:34.080 of a technology ben Well, I so ironically I made 0:07:34.080 --> 0:07:36.160 my way to the West Coast, not from the East Coast, 0:07:36.160 --> 0:07:39.360 but via London, because if you recall, Meryll sent me 0:07:39.440 --> 0:07:41.960 to London. And when I was in London, I had 0:07:42.000 --> 0:07:44.000 spent maybe you know, two years with the bank, and 0:07:44.080 --> 0:07:46.760 the classic length of these programs is two years and 0:07:46.760 --> 0:07:49.440 then they expect you actually to move on, you know. 0:07:49.520 --> 0:07:52.320 So analyst programs are two years of investment banks. So 0:07:52.360 --> 0:07:54.320 I spent two years. They offered me a third and 0:07:54.360 --> 0:07:56.920 I really want to be quote unquote in industry. Now, 0:07:56.920 --> 0:07:58.560 I had no idea what that meant. That I wanted 0:07:58.600 --> 0:08:01.120 to work for one company, and so I was able 0:08:01.160 --> 0:08:04.040 to secure a role with the cfo UM at a 0:08:04.080 --> 0:08:06.760 company called British Guy Broadcasting, one of the biggest satellite 0:08:06.760 --> 0:08:09.760 broadcasters in the world. Um, he recalled, this is part 0:08:09.800 --> 0:08:13.520 of news corps, kind of empire and uh. And luckily 0:08:13.560 --> 0:08:15.720 for me, I parlayed my job in finance to a 0:08:15.800 --> 0:08:18.239 job in finance inside of the company at at beast 0:08:18.240 --> 0:08:21.400 I B and then I was promoted to working UM 0:08:21.440 --> 0:08:25.320 for the CEO and the CEO UH there. So actually 0:08:26.080 --> 0:08:29.000 it's probably more dramatic story. I was promoted. I was 0:08:29.040 --> 0:08:31.920 working first on the top floor for the you know, 0:08:31.960 --> 0:08:34.560 one of the two top bosses. And I've been there. 0:08:34.960 --> 0:08:36.960 I've been at beast IB for only a year. And 0:08:37.000 --> 0:08:39.240 I walked into my boss's office and I told him 0:08:39.240 --> 0:08:41.920 I quit. And he was shocked, and I said, I said, 0:08:41.920 --> 0:08:43.959 you know, I said, two things are true, David. Number one, 0:08:44.600 --> 0:08:46.439 I have this epic promotion. You know, I you know, 0:08:46.480 --> 0:08:49.000 I sit down the hallway from you. I get I 0:08:49.040 --> 0:08:51.199 get lunch every day. I'm on the you know, I'm 0:08:51.200 --> 0:08:53.320 on the executive floor. I'm like, but you don't really 0:08:53.440 --> 0:08:55.120 use me. And it was true. My boss was very 0:08:55.200 --> 0:08:57.480 used to sort of operating like the load wolf is 0:08:57.520 --> 0:09:00.840 that UM as a sort of effectively president a company 0:09:00.960 --> 0:09:02.400 and I said number two, I think I want to 0:09:02.400 --> 0:09:04.120 head back to North America. I've been there for two 0:09:04.160 --> 0:09:06.640 and a half years. And a girlfriend of mine, a 0:09:06.720 --> 0:09:09.079 very dear friend, was at Stanford Business School. I had 0:09:09.160 --> 0:09:11.760 visited her the year early earlier, and I fell in 0:09:11.800 --> 0:09:13.959 love with the weather in the Bay Area and this 0:09:14.120 --> 0:09:16.520 kind of sense of entrepreneurship. That's true. I mean for 0:09:16.559 --> 0:09:19.280 a girl who comes from you know, Ontario, Canada, where 0:09:19.320 --> 0:09:22.720 it gets pretty dark cold. You know, once you visit California, 0:09:23.240 --> 0:09:25.520 you sort of realized that it's possible to live in 0:09:25.559 --> 0:09:28.400 good weather all year long. Um. But the other but, 0:09:28.440 --> 0:09:30.559 the other truth was I wanted to be an entrepreneur. 0:09:31.040 --> 0:09:33.440 My father, you know, loved writting, Zoe love business. I 0:09:33.480 --> 0:09:36.319 had no idea how. I loved the Bay Area for 0:09:36.360 --> 0:09:38.120 the weather, and I sensed that it was you know, 0:09:38.200 --> 0:09:40.679 that there were a lot of people starting companies. So 0:09:40.760 --> 0:09:43.840 I put my job. I um went skiing for three 0:09:43.840 --> 0:09:48.280 months in Whistler, um, and I moved to the I 0:09:48.360 --> 0:09:50.960 moved to California and bought a car, drove up the 0:09:51.000 --> 0:09:53.920 coast from l A to San Francisco. Luckily that that, 0:09:54.000 --> 0:09:55.920 you know, those friends of mine, their parents put me 0:09:56.000 --> 0:09:58.880 up at their very nice house and California until I 0:09:58.880 --> 0:10:02.400 found a job and I started over, how did you 0:10:02.480 --> 0:10:05.760 end up at? If you can't tell already? I was 0:10:05.760 --> 0:10:09.480 assarily impatient, uh, young woman, because you know I moved 0:10:09.520 --> 0:10:12.640 to Farembound in that first six years of my career. I, 0:10:12.960 --> 0:10:15.040 as I said, I you know, I was looking for 0:10:15.080 --> 0:10:18.120 a job in the valley. I faund when and forlting 0:10:18.200 --> 0:10:20.880 the job I found, who was not nearly as positive 0:10:20.880 --> 0:10:23.480 and experience as I had hoped. Um as you as 0:10:23.520 --> 0:10:25.480 we just talked about, I actually had a really good 0:10:25.480 --> 0:10:27.960 experience at Meryll. I even had a good experience at 0:10:27.960 --> 0:10:29.720 Peach Guy b if you look at the fact that, 0:10:29.800 --> 0:10:32.840 you know, I got the ability, I was promoted and 0:10:32.880 --> 0:10:35.280 I got to this. You know, I found a startup 0:10:35.280 --> 0:10:37.800 in Silicon Valley that was an interactive television which was 0:10:37.800 --> 0:10:39.560 you know, at least somewhat related to what I'd just 0:10:39.640 --> 0:10:42.360 done it, you know, a sky was in the TV industry. 0:10:42.840 --> 0:10:44.760 And then second day on the job, my boss told 0:10:44.760 --> 0:10:46.600 me I was scared the secretaries, and I was like, 0:10:46.679 --> 0:10:49.640 what what does that mean? What do you mean? What 0:10:49.679 --> 0:10:51.199 do you mean? I'm like, I've just come from two 0:10:51.240 --> 0:10:53.880 industries that are highly male dominated, nobody ever told me 0:10:53.920 --> 0:10:56.760 I was scary and um, and thus began a rapid 0:10:56.800 --> 0:10:59.320 decline in our relationship. I felt like I wasn't getting 0:10:59.320 --> 0:11:01.400 a lot of response ability. He kept telling me I 0:11:01.480 --> 0:11:03.760 was the rookie that needed to be coached, and I 0:11:03.840 --> 0:11:07.560 quit six months later, actually fairly deflated, because I was like, Wow, 0:11:07.600 --> 0:11:09.880 if this is what it means to be in Silicon Valley, 0:11:09.960 --> 0:11:12.760 its supposed to be this meritocracy, you know, I'm supposed 0:11:12.760 --> 0:11:14.559 to be, you know, having the time of my life. 0:11:14.840 --> 0:11:18.480 Maybe I'm not meant for this place. Luckily for me, UM, 0:11:18.520 --> 0:11:20.960 I started to think about getting another job, and a 0:11:21.000 --> 0:11:23.959 recruiter called and pitched this idea of you know, a 0:11:24.040 --> 0:11:28.960 company started by four Stanford PhDs in um I had 0:11:29.000 --> 0:11:32.160 this very cool technology. I took the interview. I didn't 0:11:32.200 --> 0:11:36.120 really understand fully the technology, but I loved them. They 0:11:36.160 --> 0:11:40.560 were smart, they were candorous UM, and so I switched, 0:11:40.760 --> 0:11:43.400 and lucky, luckily for me, I made that switch. You know, 0:11:43.640 --> 0:11:47.680 um Jungly ended up building a whole engine for shopping 0:11:48.240 --> 0:11:51.280 for compared and prices across the Internet, and Amazon bought 0:11:51.280 --> 0:11:54.080 the company six months later, and that was really the 0:11:54.120 --> 0:11:57.000 start of my career in Silicon Valley just a great experience, 0:11:57.200 --> 0:12:01.120 but following a very poor one. Huh really, well, everything 0:12:01.160 --> 0:12:04.360 can all be one in roses. Sometimes they're gonna miss 0:12:04.800 --> 0:12:07.120 tell us a little bit about what it was like 0:12:07.240 --> 0:12:12.600 working for Amazon and how closely did you work with 0:12:12.679 --> 0:12:15.120 Bezos back then, Well, believe it or not, that's then 0:12:15.160 --> 0:12:17.079 it was a pretty small company. There was about twelve 0:12:17.120 --> 0:12:20.400 hundred people. We were public, so everybody got exposure to Jeff, 0:12:20.440 --> 0:12:24.160 myself included. So what are some of those earlier those 0:12:24.200 --> 0:12:26.160 early times like at Amazon. Well, first of all, as 0:12:26.200 --> 0:12:28.760 I said, everybody was you know, it was a small 0:12:28.800 --> 0:12:30.880 most company that you could fit most of Amazon in 0:12:30.920 --> 0:12:32.920 one or two buildings. That we made a couple of 0:12:32.960 --> 0:12:35.400 moves where you know, we were all in the same building. 0:12:35.480 --> 0:12:37.760 Number two. We all had to work in the warehouse, 0:12:37.840 --> 0:12:40.800 including you know, like the very top executives at Amazon, 0:12:40.960 --> 0:12:43.839 Jeff and Rick Dal's out. Like everybody had ships, had 0:12:43.840 --> 0:12:46.760 shifts over Christmas, you had no day job. You literally 0:12:46.800 --> 0:12:48.920 all had shifts in the warehouse, which was a pretty 0:12:49.000 --> 0:12:52.199 amazing cultural you know cultural feat and by the way, 0:12:52.240 --> 0:12:55.240 that included like overnight ships. Um, you were picking and 0:12:55.280 --> 0:13:00.439 packing books, music, you know, books, uds, and videos. That's true, Um, 0:13:00.600 --> 0:13:03.559 Jeff had bought the company because he believed it or 0:13:03.600 --> 0:13:07.600 not in still for still had his vision of a 0:13:07.679 --> 0:13:11.680 day where Amazon should show you every product on the internet, 0:13:11.679 --> 0:13:13.760 whether or not they had it in stock. So this 0:13:13.920 --> 0:13:17.000 early vision of marketplace. But Amazon at the time was 0:13:17.040 --> 0:13:19.440 just building out its own verticals, so what was it 0:13:19.520 --> 0:13:22.560 like He was really the main champion of this acquisition 0:13:22.600 --> 0:13:25.520 of buying us for our technology. He used it to 0:13:25.559 --> 0:13:28.800 start version one of Amazon Marketplace, which he shut down 0:13:29.400 --> 0:13:31.920 several years later. So he had made many attempts at 0:13:31.920 --> 0:13:34.800 marketplace before he got the one that worked, and by 0:13:34.800 --> 0:13:37.200 the way, before the world was ready for it. So 0:13:37.240 --> 0:13:40.000 it was pretty It was a pretty um meat look 0:13:40.040 --> 0:13:42.280 into how sort of visionary he was even early on. 0:13:42.520 --> 0:13:45.520 Of course, you know, not nearly as sort of um 0:13:45.600 --> 0:13:48.280 daunting a presence as he might be now, just like, 0:13:48.320 --> 0:13:51.640 you know, very accessible, pretty goofy actually pretty quickly sense 0:13:51.679 --> 0:13:54.359 of humor. And I got to work with them specifically 0:13:54.400 --> 0:13:58.360 because I was one of the people selling merchants, you know, 0:13:58.440 --> 0:14:00.680 like people like Macy's and others on the idea of 0:14:00.679 --> 0:14:04.160 putting their products on Amazon's website. So I got to 0:14:04.200 --> 0:14:07.320 pitch a few different retailers with Jeff, which was really neat. 0:14:07.840 --> 0:14:10.160 So I know this is going to be a very 0:14:10.240 --> 0:14:15.199 fanboy question, but I have to ask because there's a 0:14:15.240 --> 0:14:20.760 broader components about understanding or not the future. In the 0:14:20.880 --> 0:14:24.800 late nineties, in the early two thousand's, did you have 0:14:24.960 --> 0:14:29.680 any indication that Amazon would become the juggernaut that it 0:14:29.800 --> 0:14:34.480 become came or was thouse early days, Hey, we think 0:14:34.520 --> 0:14:36.600 we're going to be successful. We could be a real 0:14:37.080 --> 0:14:42.160 solid company. Like what was the view like from back then? 0:14:42.880 --> 0:14:44.880 The view was not that we were going to become 0:14:44.920 --> 0:14:49.520 the juggernaut we are today as defined by Amazon's not 0:14:49.600 --> 0:14:52.680 just a retailer, but it's like a dominant movie studio. Oh, 0:14:52.760 --> 0:14:54.960 it's not just a movie studio. It owned the grocer. 0:14:55.160 --> 0:14:57.280 Oh it's not just the grocer, but it happens to 0:14:57.280 --> 0:15:00.480 own the largest infrastructure backbones for the way it's called 0:15:00.560 --> 0:15:04.120 you know, Amazon Web services and other merchants. Like no 0:15:04.320 --> 0:15:07.480 way with that obvious, as I said, like literally, these 0:15:07.480 --> 0:15:09.720 were the days when we selling books, music and video 0:15:10.440 --> 0:15:13.240 and um launching new categories. And Jeff, as I said, 0:15:13.360 --> 0:15:17.080 like he was impressive, but he was also very accessible, funny, young, 0:15:17.280 --> 0:15:19.440 like he told me a few years older than I am. 0:15:19.480 --> 0:15:22.200 At best, and um, to know, I don't, I mean 0:15:22.240 --> 0:15:24.000 all the people that you think of now is it's 0:15:24.080 --> 0:15:27.960 quite famous. Um, there was no indication, you know, as 0:15:27.960 --> 0:15:30.600 I said, now you might and I might say wow, 0:15:30.640 --> 0:15:35.040 buying a company in launch Amazon marketplace. Certainly they were 0:15:35.080 --> 0:15:37.000 early inklings that he used a vision to sell a 0:15:37.080 --> 0:15:39.560 lot of stuff and so he could say, hey, could 0:15:39.600 --> 0:15:42.960 I see this company becoming one of the larger retailers? Sure, 0:15:43.520 --> 0:15:48.520 but is defined by what Amazon is today? Um, yeah, 0:15:48.520 --> 0:15:52.720 no way to predict it quite quite fascinating that that's 0:15:52.760 --> 0:15:58.520 quite fascinating. So let's talk about your transition from Amazon, 0:15:59.640 --> 0:16:03.520 uh to your next venture. You co founded a startup. 0:16:03.800 --> 0:16:07.400 Tell us a little bit about Yodley and what made 0:16:07.480 --> 0:16:11.000 you decide to say, well, this Amazon company is kind 0:16:11.000 --> 0:16:12.880 of fun, but let me see what I could build 0:16:12.880 --> 0:16:15.400 on my own. Well, remember we were chatting about that 0:16:15.520 --> 0:16:19.560 rather restless and impatient young woman. I don't think any 0:16:19.560 --> 0:16:21.240 of that solved when I was at Amazon. It was 0:16:21.280 --> 0:16:23.960 a great experience, by the way, And you know, remember 0:16:24.000 --> 0:16:26.720 I had never gone intending to be at Amazon. I 0:16:26.760 --> 0:16:29.320 had gone to a startup right which got bought. And 0:16:29.320 --> 0:16:32.280 while Amazon was a great company, was up in Seattle, 0:16:32.920 --> 0:16:35.920 it was now public, and so there's me thinking, gosh, 0:16:35.960 --> 0:16:37.360 what am I going to get the chance to start 0:16:37.360 --> 0:16:39.720 my own company? And I know many people listening to 0:16:39.760 --> 0:16:42.160 this podcast will be like, really, you left Amazon to 0:16:42.240 --> 0:16:46.000 start your own company? Is that a really smart decision? Um? 0:16:46.040 --> 0:16:48.240 But in some ways, you know, Amazon to me still 0:16:48.280 --> 0:16:50.880 at the time still felt very big and um, and 0:16:50.920 --> 0:16:54.600 I wanted to get there. So at Amazon and remember 0:16:54.640 --> 0:16:56.800 many of the founders of Jungle League, you know, have 0:16:56.920 --> 0:17:00.160 made a lot of wealth. Um, they're certainly mentors of mine. 0:17:00.200 --> 0:17:03.160 They are even today, and they start angel investing in 0:17:03.200 --> 0:17:06.159 a number of companies in the valley. And knowing that 0:17:06.280 --> 0:17:09.600 I have this ambition. Um, I've been at Amazon about 0:17:09.680 --> 0:17:12.520 a year and I get into day. I get a 0:17:12.560 --> 0:17:14.959 call one weekend and sort of says, hey, you know, 0:17:15.040 --> 0:17:19.800 there's this professor from UCSC who's a computer science professor, 0:17:19.840 --> 0:17:22.760 and he's built this really cool technology that goes out 0:17:22.800 --> 0:17:25.840 across the web and it gets all your financial information 0:17:25.920 --> 0:17:28.640 behind all of those sites with passwords, and it puts 0:17:28.720 --> 0:17:30.880 them in one place. You can have an aggregated view 0:17:30.920 --> 0:17:33.440 of your financial life. And by the way, the technology 0:17:33.480 --> 0:17:36.000 is not the same as Junglie, but it has some analogies, 0:17:36.560 --> 0:17:38.960 and they're like, and they're looking for a business co founder. 0:17:39.000 --> 0:17:40.760 They have all these engineers that they need somebody to 0:17:40.840 --> 0:17:44.119 establish the business model, race the money. Um. And so 0:17:44.160 --> 0:17:46.080 I got one of those inbound calls and it was 0:17:46.119 --> 0:17:50.320 through that network of you know, angel investors who who 0:17:50.400 --> 0:17:53.360 were the founders of Junglee. I flew down from Seattle 0:17:53.440 --> 0:17:55.800 to San Francisco for a weekend. I took one look 0:17:55.800 --> 0:17:59.800 at the technology and I suitably impressed. I was like, Wow, 0:18:00.359 --> 0:18:02.720 you just grabbed all my credit card balances and my 0:18:02.840 --> 0:18:05.440 bank balance and you know, my brokerage balance in one 0:18:05.480 --> 0:18:09.120 place and gave me this egrecated You nobody can do that. 0:18:09.480 --> 0:18:13.719 I'm just pretty revolutionary technology at the time. Um. And 0:18:13.920 --> 0:18:16.480 they offered me the opportunity of twenty nine years old 0:18:16.560 --> 0:18:19.000 to become what's called a co founder of the company 0:18:19.040 --> 0:18:22.280 and the first business executive. And I just jumped at 0:18:22.280 --> 0:18:25.280 the chance. I love the technology, UM. I love the 0:18:25.280 --> 0:18:27.800 fact that I would be with There was five engineers 0:18:27.800 --> 0:18:30.159 at this company too, again very similar to Junglie. But 0:18:30.200 --> 0:18:31.560 now I was going to get a seat at the 0:18:31.600 --> 0:18:34.520 table as you know, as literally one of the executive 0:18:34.520 --> 0:18:36.520 team at such a young age and get to raise 0:18:36.560 --> 0:18:39.560 the money from venture capitalists, right a business plan. So 0:18:39.880 --> 0:18:44.000 uh so they were really very early stage. Yes, yes, yes, 0:18:44.080 --> 0:18:46.320 I mean it was twelve engineers in a room. And 0:18:46.440 --> 0:18:49.119 as I said, and and I was just, you know, 0:18:49.200 --> 0:18:52.000 as effectively the first business leader to be hired at 0:18:52.000 --> 0:18:56.359 the company. And so I uh, I gave my notice 0:18:56.400 --> 0:19:01.120 at Amazon maybe a month later and moved right into 0:19:01.200 --> 0:19:04.040 Jungle Lee And we raised fifteen million dollars from venture 0:19:04.080 --> 0:19:07.320 capitalists within a month of that, and we were off 0:19:07.359 --> 0:19:09.399 to the races. And you know, thus began kind of 0:19:09.400 --> 0:19:11.879 a six year journey to build you know what today 0:19:12.000 --> 0:19:15.600 many would consider the pioneer in really aggregating your financial information. 0:19:15.640 --> 0:19:18.320 I'm really proud of the fact that Yodally really did 0:19:18.359 --> 0:19:21.600 create a whole industry of companies that you know, we're 0:19:21.640 --> 0:19:25.120 able to access financial information using our services and our 0:19:25.240 --> 0:19:28.520 kind of technology backbone and build many of the financial 0:19:28.520 --> 0:19:32.520 apps that you know people used today. Um so Yodally 0:19:32.960 --> 0:19:35.200 Yodally had a fifteen year run before it became public, 0:19:35.240 --> 0:19:37.280 and I was there for the verse five of those years. 0:19:37.400 --> 0:19:40.640 So let's work our way through this chronology a little bit. 0:19:40.760 --> 0:19:44.600 You end up at at Jungle which gets acquired by Amazon, 0:19:44.720 --> 0:19:51.960 and from to I'm at Amazon, and then when do 0:19:52.000 --> 0:19:55.399 you leave ninety? When do you leave amaz Oh? So 0:19:55.560 --> 0:19:59.159 you were only okay, Actually, so when their year, I 0:19:59.160 --> 0:20:03.080 mean it was year and you stayed. Um, did you 0:20:03.160 --> 0:20:06.679 stay with Yodley until they were acquired by investment? No. 0:20:06.840 --> 0:20:10.200 I stayed with Yodley for five years. In that time, 0:20:10.240 --> 0:20:13.040 I had every job under the sun. I was predominantly 0:20:13.080 --> 0:20:16.639 responsible that we've talked about for uh for not just 0:20:16.720 --> 0:20:18.600 raising the money. We raised about a hundred million in 0:20:18.640 --> 0:20:21.400 the time I was there, in several rounds of financing, 0:20:21.480 --> 0:20:24.639 but I was I was responsible for sales and business development, 0:20:24.680 --> 0:20:28.080 selling our technology to all the banks and brokerage companies. 0:20:28.200 --> 0:20:30.399 And so I stayed until two thousand and four. I 0:20:30.440 --> 0:20:33.399 helped us hire our CEO in two thousands, and he 0:20:33.440 --> 0:20:35.560 wasn't going anywhere, by the way. So I always say 0:20:35.560 --> 0:20:37.879 to people, I topped out at my own startups. Like literally, 0:20:37.920 --> 0:20:40.520 I'd had every job I've done, sales at Den Marketing, 0:20:40.520 --> 0:20:43.560 at don PR, I was our spokesperson, I raised money, 0:20:44.080 --> 0:20:46.280 and I in many ways, I was, you know, partnered 0:20:46.359 --> 0:20:49.399 very closely with the CEO and we had a great relationship. 0:20:49.960 --> 0:20:51.879 And in two thousand and four, I was like okay, 0:20:51.880 --> 0:20:54.320 and now like what's my next horizon? Like I've been 0:20:54.359 --> 0:20:57.000 here five years and I've done all of these roles, 0:20:57.000 --> 0:20:58.960