Throughout her career, Jamie Hansen would often find herself at a juncture where a leap was necessary—whether inside an imploding industry, unsustainable business partnership, or mismatched corporate structure. Where some people would see high risk, she just saw something to navigate through. Eventually, that outlook prepared her for what she'd face in her personal life, too. Find out how defining risk is all in the eye of the beholder on today's Roads Taken.
Throughout her career, Jamie Hansen would often find herself at a juncture where a leap was necessary. She first needed to navigate a start in the start-up world on the wrong coast and then got to the Bay Area just before the dotcom bust. She then needed to navigate her way from web development roles to solutions engineering to find more stability. But the stability afforded by a big company didn’t fit with her personality and so she took another leap into food entrepreneurship.
Along the way, where some people would see high risk, she just saw something to navigate through. Eventually, that outlook prepared her for what she'd face in her personal life, too.
In this episode, find out how from Jamie how defining risk is all in the eye of the beholder…on today's Roads Taken, with me, Leslie Jennings Rowley.
About This Episode’s Guest
Jamie Hansenan experienced solutions leader currently working to help a startup in the procurement space, Zip, move to the next level. She has worked at companies companies large—including Salesforce—and small—including her own wholesale bakery business. She lives in the San Diego area with her twin girls, living it up by the water and basking in the sunshine.
For another story about leaping across careers with baked goods and family in the middle, listen to our episode with Chesley Homan Flotten.
Find more episodes at https://roadstakenshow.com
Executive Producer/Host: Leslie Jennings Rowley
Music: Brian Burrows
Email the show at RoadsTakenShow@gmail.com
Jamie Hansen: The risk is gone. Here I am. I’m at this big, stable company, I have a very stable paycheck. I realized that if you kind of looked at everything I'd done up to that point, it was just all these like series of very short steps that seemed very comfortable and easy at the time, and landed me in a place that was definitely stable and I, it just was like, this is, this is not it.
Leslie Jennings Rowley: Throughout her career, Jamie Hansen would often find herself at a juncture where a leap was necessary—whether inside an imploding industry, unsustainable business partnership, or mismatched corporate structure. Where some people would see high risk, she just saw something to navigate through. Eventually, that outlook prepared her for what she'd face in her personal life, too. Find out how defining risk is all in the eye of the beholder on today's Roads Taken, with me, Leslie Jennings Rowley.
Today I'm here with Jamie Hansen and we are going to talk about finding our way on a path and getting maybe tempted by sweets and other kinds of sweet things and where it puts us when we come through that. So Jamie, thank you so much for being with us today.
JH: Thanks for having me. So you know that I start this the same way with each of my guests asking two questions and they are these: When we were in college, who were you? And when we were getting ready to leave, who did you think you would become?
JH: I, when I was in college, I was sort of struggling with the difference between sort of what my ambition for myself was and sort of where I found myself. And I think the thing that was sort of surprising when I started. At Dartmouth, I'd had an experience going into high school where I had gone from a public school to a private school. And my first, my freshman year, I didn't know anyone and I was very quiet and I didn't exert myself a lot, mostly out of fear and anxiety. And in my sophomore year, I remember speaking with somebody who said, You know, I really just thought you were super stuck up and it was this really sort of interesting insight because it was like me being quiet and into myself and I thought, when I arrive at Dartmouth, I, I have to, like, embrace things with both hands and I'm gonna kind of go do, do all this stuff.
And I, I thought I was gonna be this like actress, that's what I thought I was gonna do. And. Like my freshman trip, one of the leaders of my trip was on the rugby team and I was like, oh, I'm gonna go do that. And suddenly, like, I kind of went off in a different direction than, you know, but I sort of had this thing where I found myself in a place of being very, somewhat like unwilling to take risks to the point where when I left Dartmouth one of the things I regretted was I never went on a foreign study program or a language study abroad program. And I thought like, God, what did I, like, I missed this opportunity. And it was, in hindsight, it was like, I didn't really put myself out there to take the risk and try to figure it out cuz I, I had all these kind of concerns about it and that I couldn't overcome.
LJR: But you did do rugby, which has a lot of risk in it and was, I mean, physical risk, right? But like also that wasn't, you were going on a stage and then this person said this and you were open to something new. So how do you align those?
JH: Well, the funny thing is I never really connected it with the concept of risk. Like, to me it wasn't risk because I had, I was a goalie in soccer in high school.
LJR: Okay.
JH: And so for me it was like, oh, goalie rugby, that's like, not that, not that big a deal. And, and it was something where I felt like, well, I can learn that. Like, that's not, not a risk for me because I see something in front of myself and I can try it and I can figure things out. And I, so I sort of disconnected this idea of like taking a risk from like, things that I felt like I could just do.
And that sort of plays into what ended up happening as I was leading Dartmouth, because I remember feeling senior year, it was like I was looking around at all these people that were like doing recording and I'm thinking, what did I miss? How did all these people know what they were supposed to be doing?
And I, it felt like the class was sort of split between the people that just apparently knew how to play the game and they were already on this path from like way earlier that I somehow missed the boat on. And then there's other people that were like, I have no idea what I'm doing and graduating with no plans.
And I was kind of somewhere in the middle, like I ended up going through recruiting, but in a very limited capacity. Now, I was an engineering major and my minor was painting and my first job outta college, I, I went to work for a marketing consulting firm in Westport, Connecticut, which was very kind of random, but I remember feeling like my parents paid for my education. And I felt so much guilt and responsibility about like, I have to get a job immediately after school. I can't have any question, like I have to go be self-sufficient because I, I cannot, I can't fail. And it was the, it was kind of like this quick and easy path for me to figure something out without really, this, this is kind of why it goes back to risk for me was like, I didn't really have to think very hard to kind of get this job.
It was sort of in front of me and okay, I can do that, so I'm just gonna go do that. And it kind of put me on a path that ultimately was sort of interesting in that by total luck as I was a year into this consulting role and going, God, you know, like in my engineering major, what I liked about it was like I could do stuff, I could make stuff, I could build stuff.
And in consulting you told other people what they should be doing and whether or not they actually followed through with it was completely random, right? And it just felt very, Like powerless and like, I'm like, what am I, what am I doing? You know? Especially here I am this like 21, 22 year old kid, like telling grown adults how to do marketing and I remember having a client ask me when I'd gotten my MBA and I was like, oh my God. Like right, what am I doing here? This is, and so the funny thing was I had had this sort of interest in the internet. Like my first exposure to the internet I remember was I was a UGA junior year and I remember them taking us for training and putting us in a big auditorium and having these guys from Kiewit like make this presentation about what the worldwide web was. And I was like, and they're like, you're gonna need to know this because incoming freshmen are gonna know what this is and they're gonna, you know, you have to be like, you have to like be informed about this.
LJR: That was smart of them. Yeah.
JH: And I remember just thinking like, this is really interesting to me. And so maybe, maybe this consulting thing, like the internet seemed to be kind of blowing up and I was like, maybe I need to go run away and join the internet. I don't even remember how this happened, but somehow I managed to wrangle some interviews where like, I flew across the country to San Francisco to go like interview with some people for like a project management type of role in these like web development shops. And I came home and one of the consultants that I worked with, who I didn't quite realize it at the time, had started a software company like 10 or 15 years before that had failed. And I said, John, I gotta leave. I like, I can't do this consulting anymore. I think I'm gonna go move to California and get a job somehow working on the internet. And he said to me, Stop. And I was like, what? He goes, I just got money from like the founder of the consulting firm had basically just offered him some funding to basically start a software company
LJR: within…
JH: And I was like, and he is like, come work for me. I was like Okay. And so the next thing I knew, I was literally moving upstairs and we kind of had a couple of office spaces in the same building that I had been working in with like all the people that I've been working with. Only now it was me and this consultant. And he had two other people that had joined the team that he'd hired. And he’d had some consultants that he hired. And the next thing I knew, I was working for a software startup.
LJR: In Connecticut,
JH: In Connecticut, in Westport, Connecticut. So…
LJR: Okay. Can I ask you, did you think that was risky at the time? [JH: No.] Or was it one of these? [JH: I don’t know why.] This was right in front of me, right? This was right in front of me. I'm taking advantage of it. I can do it. He thinks I can do it. We'll figure it out together. So you didn't see the risk in that?
JH: No. No.
LJR: Okay.
JH: It was just like, okay, I'm gonna…
LJR: Because the ecosystem of software startups in Connecticut was…
JH: Very tiny.
JR: Yeah. Okay. Yeah.
JH: And it was pre-dotcom bust. Like everything, everywhere people were giving away money. And the tragic thing about the software startup was that the guy that had started the company, when he had started the previous software company, he basically started what was a precursor to Quicken. And when he launched that product, he basically beat the adoption of home PCs, like he was like a year or two early. And so he didn't have enough of a market to actually sell the software to, to people cuz they weren't ready to buy it yet. And then Quicken came on like literally two years later and like became the defacto standard. And so his concern here was that we were trying to get into the internet faster than broadband was ready. The people were ready to really have like fast internet service at home. And so he hedged his bets by saying, well we're gonna build some desktop software first and then we'll build the website and build the internet product like later. And that's what killed us.
LJR: Oh no.
JH: So in the meantime, while I was working there, I ended up moving into New York. So I moved in with, at the time Chandra Stanley had, we had this sort of apartment in New York that. Sara Sabin had passed to Chandra and then kinda got recycled through a bunch of friends. Anyway, so I ended up moving into the city. So I was doing this reverse commute to Connecticut and trying to make this work. And I basically got to this point where the person that we'd hired as the CTO kind of said to me, he's like, this is, this is gonna fail and you should probably get out. So I had been sort of playing, wearing many hats as people do in a software startup by head. Sort of, I was acting as like project manager. I was writing all the help manuals for the, for the product. I started up our customer support center. I, you know, would drive to wherever it was…we printed these DVDs and like got it printed. Like it was kinda whatever was happening. But one of the things that I was doing was I was helping to design what we were gonna build into the website. And I thought, well, of all these things that I do, like, that's what I like. I like the design aspect. For me, it was this combination of like design and building, which is, you can think about it, like that's what I did at Dartmouth. It was like, and so I thought, okay, well that makes sense to me. So now I'm like, how do I get a job doing this? And I somehow put my resume out on the internet and this guy calls me and he's just like, Hey, I have a job for an information architect that I think you should apply for. And I was like, okay. And at the time, information architecture was sort of a precursor to what is now considered like user experience design in software.
And so I bought a book by this guy who was sort of like the guru of information architecture. And I read this book, like start to finish, and I…to prepare for this interview…and I go to this interview and the guy that interviewed me, it was at an ad agency in New York that had started a software development arm so they could build websites for their advertising clients. And he interviewed me and I basically regurgitated this guy's book, like his whole methodology. I just sort of spit it back as if I knew what I was talking about. And it turns out that he had hired that guy as a consultant, so I was telling him everything that he wanted to hear. I was literally playing back to him. [LJR: Awesome.] Oh, you know, he was a disciple of this guy and this is, it couldn't have been more random. This was the only interview that I [LJR: Right.] basically had, and I got this job and so the next thing I know, I'm like, I'm now live, living and working in Manhattan for this ad agency and I'm in this little tiny kind of fishbowl room inside this larger ad agency. It was, it was Deutsch, so Donnie Deutch who kind of went on to sort of infamy. [LJR: Yeah.] And randomly I sort of worked very closely with a couple of sort of people that, that in the end kind of also sort of foreshadowed like where my career was gonna go. One of whom was someone who was a guy named Matt. Matt and I would talk about baking and cooking all the time, and Matt's like, Jamie, we should start a bakery. And I'm like, yeah, sure, Matt. Like, let's do that. And the funny thing, and I, you know, blow the lead, but Matt did end up starting bakery and I did too, but at very different times down the road.
LJR: That's funny. But, so, but give me times. So we're, you're at Deutsch, like late, late nineties, right?
JH: Yeah, so it's like, it's probably like 98, 99. Okay. And I'm working for this ad agency and the problem is that ad agencies did at the time, didn't understand that building websites was big, was building software. So they just saw that they just like change their mind overnight, you know, a customer like in advertising, customer would see a visual and they'd go, oh no, I don't like that. Change this. And they'd go, okay, well that's what they were doing. And so I was spending all of my time trying to like keep our development team. It was, it was like a third party that we hired, like getting them sort of doing this stuff as fast as they could, but they were literally getting this like stream of changes and I was just in this environment that was so crazy and everyone around me was talking about like how we had to leave. And one day, this woman that I, another producer that I worked with, who literally sat behind me. She and I would, would back into each other if we, if we, if we pulled our chairs back and she said, Hey so my boyfriend just got some money from Goldman Sachs and they're gonna start this software company and he's interested in interviewing somebody for your role. So, you know, would you be interested in talking to him, like either to help him out or, I don't know if you're interested in this.
And so the next thing I know, I'm talking to her boyfriend and he's just like, you know, are you interested in it? And I was like, Yeah. Okay. I think I am. So yet another, so now, okay, now I'm onto my next job. So meanwhile, part of the reason I think in looking back that my concept of sort of risk is that my dad like worked for the same company for like 35 years.
LJR: Yeah.
JH: And he had grown up with like not a lot of money. And for him, like financial stability and security was a huge thing. And that had been sort of beaten into me, you know, from the, from as long as I could remember. And so here I am going to my dad and saying like, Hey, yeah, so I'm gonna, I'm gonna. I'm gonna quit another job and like go to work for like the fourth company in like four years. And he is just like, what are you doing? You know? And I'm like, yeah, but I think it's gonna be okay. Like, I had all this sort of, in my head I'm thinking, you know, I like, everything's telling me that like, this thing isn't gonna die and that this is a sustainable, like this, this career is gonna go somewhere. I just can't conceive of where it's gonna go because.
LJR: It's new.
JH: It's so young that it's new and nobody, nobody knows what's supposed to happen. And I'm like, but I think it's, I, I think, you know, I think other people are sort of in the same boat. It didn't seem to be just me doing this. It was kind of like, okay. And so I jumped ship and I went for, worked for another startup and that was another like six months of me just like killing myself and working really hard and realizing that the guy that had gotten the money had no idea what he was doing and just…I remember I was working all kinds of hours. We were trying to, you know, build this website together and it was just the most, you know, frustrating experience of my life. And I remember like going to the gym on a Friday night and coming home and like, like I was literally started crying at the gym. And I came home and Chandra looked at me and she's like, maybe you need to think about another job. And I thought, okay, I've gotta get out of this, you know, like endless hamster wheel. And at the time it was like, well I was, I was born and raised in California and I thought if I don't move back to the West Coast, then I'm gonna get stuck here. And I don't know that that's what I wanna do. Like I felt like I was spending all my money flying across country to see my family and I missed going water skiing. And I missed, like I, New York had started to feel very like concrete-bound to me. And you know, for a girl who was born and raised in Southern California, I was like, I need a little bit more sun and water and whatever. Now, not that San Francisco was sunniest place in the world, but at least it was close enough, close enough that I could get to the beach, that I could get to the snow. And like all of that was reasonably accessible to me. And there were all of these big web development shops in San Francisco that had now become kind of big, stable institutions. So I thought, okay, this is my path. I'm gonna go get a job at one of these big companies that have steady clients, and now I'm gonna find a place and I'm gonna stick with it. And this was September of 2000.
LJR: Yeah. Yeah.
JH: That's why I interviewed with like six companies and I, you know, got this job offer and actually it was sort of like the one that I maybe least wanted, but it was a job and I had a place, you know, someone's gonna move me to California and Okay. And so I did that and I said goodbye to New York. I moved to San Francisco. I like crashed at my aunt's apartment for like three months until I could find a place, cuz at that point everybody was like queuing up in line to put their resumes out to get into an apartment. I started this job just after Labor Day, not realizing that they had done their first round of layoffs the week before I got there.
LJR: Ah.
JH: And I had some really great clients. You know, my first, my first client was Virgin Atlantic and I was working for Disney Parks and Resorts, and it's like all these like really awesome customers. And I was doing some really interesting design work and just feeling like, okay, this is great, you know? And then you know, things started getting a little grim.
LJR: Yeah.
JH: So this office had about 250 people when I started in that September. By March we were down to 60, and then the company basically sold the office to this other consulting firm because there were a bunch of things that just kind of happened and things were getting going from kind of bad to worse. We had a had a point where they were gonna close the office and the consulting firm had been owned by this parent company. And the parent company said, well, if you guys can just finish this one project, tell us how long it's gonna take you to finish this project. You know, we'll pay you guys to stay and finish this project. And we said, okay. And so we had one project left for Disney and. We were down to 11 people.
LJR: Ugh.
JH: And we finished the project and we started selling the work, like more work to Disney and more work to other other customers. So we did a partnership with a software company and I was like, Hmm, I wonder if I could go work for that company cuz they're actually doing well and like maybe that's the direction I should go. So that was my first segue into what then basically became my sort of career trajectory with what's known, known as solution engineering or sales engineering. So I moved to this other company, I did some consulting, implementing their software, and then eventually moved into their sales organization. Basically it's like the technical side of the sale. So as a solution engineer or sales engineer, you're selling the software, you're talking to customers about how it works, you're kind of showing them how it'll fit within their organization. But I basically ended up going to work for a very large software company eventually, and got there and I had this moment of like, oh my God. Like how? How did this happen? How did, how did I end up in this job working for this big company and selling stuff that I don't really like or believe in? But here I am
LJR: And the risk is gone.
JH: And the risk is gone. Here I am. I bet this big, stable company, I have a very stable paycheck. Have, you know, all these great benefits and I'm kind of miserable.
LJR: Yeah.
JH: You know, I realized that if you kind of looked at everything I'd done up to that point, it was just all these like series of very short steps that seemed very comfortable and easy at the time, and landed me in a place that was definitely stable and I, it just was like, this is, this is not it.
I remember going to Becca Graves, I went to her wedding and I remember having this like moment. I was having conversations with people there, like while I was there and I, we went, I went on a trip with a couple folks after, and I just remember hitting the spot where I was like, Hey, I'm not in a relationship and I haven't had kids, which I've always known that I wanted to do, and I'm really miserable in my job and I can't figure out what to fix first. So that's when I decided therapy was a good idea.
LJR: Okay. Okay.
JH: Spent a little time, spent a little time searching and, and sort of what that did for me was it sort of, let me kind of separate I think how I was thinking about all this stuff and I started doing some soul searching and I realized that for the first time, you know, ever I was trying to think through like how do I create something out of nothing? Like if I could do anything, what direction would I, would I go and what are the things that excite me? You know and kind of that idea of risk was sort of put aside because I sort of looked back and I was like, well, everything I've done is to your, you know, to your point, like kind of was sort of risky and I managed. I've never been in a place where I've been unemployed. I've never been in a place where I couldn't sustain myself.
LJR: Right.
JH: And now it's like, okay, so what do I wanna do? And the funny thing was that I went on a surfing trip and I met this guy and I started dating him. And he was telling me about, he was like biking halfway across the city to go to go to this ice cream shop. And I'm like, excuse me? Like you're literally biking across San Francisco, the hills of San Francisco to go buy ice cream. Like explain this to me. So I was like, Hmm, ice cream seems like something I could totally do. And I had all these like, and I’d basically come up with all these sort of food concepts because the things that I was sort of looking at was like, well, what are the things that I'm interested and I'm interested in kids and I'm interested in food and is there a business in any of those things? I was making up concepts for like home meal delivery services well before they even existed. And I was thinking through all these things, but everything had some like a lot of like logistical things and I was like, I don't know if I can quite work my way through that. But ice cream felt very manageable. It was like I could make ice cream and so I just started making a lot of ice cream, like a lot of ice cream, like, you know, six to 10 batches of ice cream a week and was like, if I can figure this out…And there were, at the time, there were a couple of sort of very, what, what then became sort of very well-known like organic ice cream shops that opened up in the Bay Area. And so I started like, hunting around and talking to people, and somebody had given me a tip that there was this nonprofit in San Francisco, it's called the Renaissance Entrepreneurship Center, and they taught a class, it was like a business planning class. You took the class and they helped you write a business plan. And I was like, okay, that seems like something I could do because I needed somebody to hold me accountable. Yeah, for something. And so I had basically, before I did that, I quit my job at the big stable company. I got a job with a consulting firm and I thought if I can sort of make my own hours and sort of like work enough to afford for me to explore this, then I can, you know, pursue this.
And so I wrote, what is the probably the most absurdly long business plan that anyone ever has written for an ice cream shop. It was about 75 pages long. If anybody's looking to write a business plan, I will tell you, don't ever do that. That's really terrible idea. But what it did for me was it gave me the guts to go home to my father and say, Dad, I'm gonna quit my really lucrative software career to go become the ice cream lady. Like that was, that's what I was gonna do. And because I had thought it all through and read everything out in his business plan, which by the way, he read and gave me notes on like, you know, every page. And we went through it line by line, and I had convinced him that this was actually a viable business.
And so I went to a ice cream convention and I went to an ice cream, like a commercial manufacturing seminar. And I, you know, did all the things. And so now I was like, okay, so how do I start an ice cream business when I only have sort of a limited number of, you know, amount of capital to do this, and it's just me and what do I need to do to make this happen? And randomly I met this guy who happened to be a pastry chef, and I was like, well, you're handy to know. And so I started talking to him and he wanted to start a business and we had been kind of talking through some concepts and randomly this retail bakery in Alameda had posted this ad online saying, Hey, we have this bakery with all this equipment and we're looking to sell. Like if you wanna buy, if you wanna rent this place, we'll give you all the equipment. Oh. And we were like, oh my God, this is like too good to be true. I can't, you know, I can't believe this is happening. And so we go and we're all in on getting this place. And then very shortly after we got sucked into what turned out to be like a complete fraud.
This couple had had this bakery and they had sold the bakery to one of their former employees and who had rented the bakery and kind of driven the business into the ground. And they were looking for a way to strong arm this family into like, selling it back or getting rid of it. And they somehow kind of implicated us in this whole thing.
So in a matter of like, after spending like three months investing time and energy and buying equipment and getting it, getting everything ready, we basically figured out that this is what was going on and now we had to pay, you know, an attorney lots of fees to get us like extricated from this whole scenario.
So here we were with everything that we would need to kind of start a bakery, or at least most of it, and no bakery. And now it's like, what are we gonna do? My business partner called me outta the blue and said, Hey, I just got a lead on this pop-up market that's happening in Oakland. And they are, you know, it's being run by these very like, well-known chefs and like, if we do this and we get, you know, accepted, we could do these like markets and sell our stuff. And I was like, okay. And so, we did a put together a tasting and they tasted it and they said, oh, okay, this is great. And, I said, Brian, I said to Brian, I'm like, what are we, what are we making? I was like, we need like a signature product. And he said, well, we're gonna make a Kouign-Amann. And I'm like, okay, I'm a big foodie and I've never even heard of this thing, like, what is a Kouign-Amann? And he, he's like, well, it's, it's kind of like a cross between a croissant and a palmier and it's made with salted butter and it's salty and sweet and it's sort of like baked in this caramel shell. And it's delicious. Everyone will love it. And I'm like, Okay, I can't spell it, but Sure. I'll figure out how to sell it.
So we ended up doing this popup, and I very vividly remember this first popup because they did like a pre-sale where, where they put up a website and people could pre-order and then, then they have, would have like a market and you'd show up and there would be all these vendors, you know, kinda like a farmer's market and you would sell your, your wares and we had sold a ton in the pre-sale that we didn't expect, and so we're baking all the stuff and I had to bring all of the pre-sale stuff over to the market and he was still pulling things outta the oven. And I was like, I had to invent a logo and packaging and pricing and everything like overnight and you know, like borrowed a tent. And I remember like driving over a bridge in the Bay Area to get to this event and I'm putting everything up and it's super windy and we're outside. And he is still like trying to finish getting everything outta the oven and packaged it up so he could bring over the rest of the stuff that we have to sell. And I am like sampling stuff as fast as I can. And, and by the time he actually got there, I had sold out and, and gotten rid of every single ounce of product that we had.
LJR: That's good.
JH: It was gone. And, and so he got over there and we kind of sold the rest. We sold out that night and. For anybody that's driven into the food world, like Alice Waters comes by and she picks it up. You know, she picks it up and takes a taste and she's like, oh my God, that's dangerous. And I was like, oh my God. Like Alice Waters just told us that our pastry is, is amazing. Like this is like a real business. And we had this moment and we, and we did it again the next month and we sold out and word started to get out.
And so it was like, you know, two months later and we were like, well, I, I think we have a business only, it's not a retail business; it's a wholesale business. So we ended up renting this spot that was ironically Blue bottle Coffee’s, like first roasting facility. It was like there was an imprint of the roaster on the floor and, but they had the vent that we needed for the oven because of the roaster.
And so we kind of set up, you know, the beginning of January and by April we had our business license and we were off to the races and we were doing, we had six customers the first week. And we were doing two farmer's markets and we were delivering seven days a week. And from that moment on, my day was kind of like this: I would get up at about seven 30 in the morning and I would go drop off a delivery at this like pizza place that this like well known chef was giving us some good press. And so I would do that and then I would come home and I'd sleep for an hour and then I'd get in the car and I would. Drive up to Davis and I would consult, do consulting work all day until like six o'clock, and then I'd get in the car and I would drive back towards the bay. And I would stop at Costco and pick up sugar and butter and sometimes, and then I would drive to back to the bakery, and then I would be in the bakery and I would be, you know, helping out with the night bake, which would go until two o'clock in the morning. Cuz our delivery drivers would come at four o'clock in the morning to pick stuff up. And I would leave there at 2, 2:30 to get home. And I'd, you know, I'd get like three hours of sleep and then I'd get up and do it again the next day. And the only difference is on the weekends I would get up and do a, you know, on Saturday I would do a farmer's market at 9:00 AM and actually Saturday and Sunday. So I basically spent like, for the better part of a year, getting about four hours of sleep at night. Doing my sort of software day job and my bakery night job.
LJR: Yeah. And that can be worth it when your partnership is good and strong, but when it kind of starts to go south and then you're pulling all these hours it's not so much. And so…
JH: And so I decided, okay, I'm done. And I basically sold, you know, sold the business to him and I backed out and it was, it was hard. It was tragic. [LJR: Yeah.] Cause it was literally like giving up my first baby. It was like, I'd put my life into doing this. This was like gonna be my big pivot and suddenly it was like all in tatters.
And so two things happened. One was that I, I went back and I started teaching the business planning class that I took to write my business plan. And that was great cuz I basically had a, had an outlet to, you know, have other people start businesses.
LJR: Just with page limits.
JH: Exactly. I would, I would be like, this is what I did, don't do this. Make sure it's a lot shorter and let me get you all through that. And at the same time, Everyone I knew kind of said, well, so the bakery's done. Are you gonna have a kid now? And I was like, yeah, I think I am.
LJR: Transferable skills: three hours night.
JH: That’s about it. You have no idea. So, yeah, so I was like, okay I, I guess this is what I'm gonna do. And it took me a couple months of like, you know, figuring out, okay, well how do I do this and can I afford to do this and what would my life have to be like? And I was basically, I'd gone back to consulting full-time. And the big software company that I used to work with, one of my friends that was still there, she's like, well, your, our old boss can hire you back. Like if you're serious about doing this, maybe, maybe you should do that. So after turning down the job and then my boss at the time saying, well, can you just maybe think on it a little bit more and see if you can make this work. And like I'll, you know, you kind of promised me the world and it's like, and I was very straight up, I'm like, look, I'm gonna try to have a baby. Like you need to understand that this is my priority. And he's like, okay. So I kind of went in eyes wide open, like, I'm gonna go back to this job and I will figure this out. And I took, you know, at first I, then I had to go tell my parents and I was like, Hey. So I, you know, I was like gearing myself up and hey, I think I'm gonna think I'm gonna try and have a kid. And they were like, yeah, we were kind of waiting for this. It's like…
LJR: We were expecting a business plan, but okay, we get it.
JH: Yeah, it's fine. Okay. So I started down that path and I got pregnant and unfortunately that pregnancy kind of ended in, in somewhat of tragedy, which was about the worst thing in my life. And I had, about three weeks before, I bought a house. And so I was in this moment of like, oh God, what did I do? Like I moved back to this company that I hate working for so that I could do this and now, so it was just kind of like, okay, I, you know, I will figure this out. And I, once again, I was like, well, maybe I need to switch jobs and I don't know if I, you know, should do this, but I, I kind of just said, well, it's probably good for me to just hold on for a bit. And so I waited and, you know, kind of waited until I was able to physically and started trying again. And the funny thing was when I found out I was pregnant, I had gone on a house boat trip and I took a pregnancy test with me. And I remember looking at it and it was like very, very faint. And I thought, I think I'm pregnant, but I don't know. And like, okay, I'm excited but I don't get too excited until I'm really sure. And I drove home and like hours later, took another pregnancy test. And this one was clearly, I'm pregnant. Oh my God, I'm pregnant. Okay. And this is exciting, but now I have all this stuff in my head about prior one. So, and then the, my health care plan was like, okay, take a blood test. Okay, take another blood test. Take another blood test. And they were giving me all these results and I'm watching my formal levels just skyrocket. And like two weeks in, I am completely nauseous. And I thought, oh my God. I'm having twins.
LJR: You just knew that in your soul?
JH: I just knew. I was like, I am having, I just knew I'm having twins and I was like, anything unlike my first pregnancy, it was just crazy and I called my mother. I'm like, mom, I'm, you just need to be prepared. I'm having twins and she's just like, no. So I go in and I go to get this ultrasound and I'm looking at the ultrasound screen, which of course if you don't actually know how to read an ultrasound, like I'm seeing three dots on the screen. And I, and the, the nurse says, oh my. And I said, well, how many are in there? And she goes, two. And I was like, oh, thank God. Good.
LJR: I can handle that.
JH: You know, like I can handle two sure, two arms, two kids. I can do that. And it was sort of like, okay, I guess, I guess I'm gonna do this like be a single mom with twins. And it was, You know, amazing. One of them had some, some like slowness growing in the womb. So it was a little bit like, you know, panic at the end. But in the end I ended up with two, you know, beautiful, wonderful daughters and that's where that four hours of sleep in the big night thing kind of came into play. Cause everyone's like, how did you do it? I was like, well, I had very thankfully, very easy infants, but I also, I learned to prioritize my sleep and that was kinda the thing. It was like, if I can get sleep, that's the best thing for me. So I just, you know, tod my kids around everywhere I needed them to go. And when they were about three months old, I had another company recruit me. So I ended up changing my job and then when they were about two and a half and I was realizing how horrifically expensive it was gonna be to send twins to preschool in the Bay Area, I decided it was time to move back to Southern California where I'd grown up and be close to my family. And so I did. So I, in like the span of two months, I packed up my whole house, like packed my kids and my au pair at the time and sent them to San Diego and moved in with my folks while my house was being built, and then moved in to my house six months later. I had gone through some, you know, kind of promotions and changes in my job at the time, and I had gotten to a point where, I had sort of picked my head up and realized that I spent about six months trying to create a job that, that they gave to one of my peers. And so I spent some moments doing some questioning of my life choices and then going, okay, well what, what's the next, you know, what do I do? And out of the blue, someone called me and said, Hey, you know, I'm working for the startup and I wanna hire somebody doing what you're doing. Could you talk to me about it? And so he, You know, called me. And I spent about 45 minutes talking to him about this, and I'm like, well wait a minute. Like tell me a little bit more about what you're doing. And he goes into full like sales mode with me and I was like, Hmm, this sounds kind of interesting. And by the way, it actually incorporated a lot of my prior experience at the big software company previously.
So, I had sort of come to the conclusion that the company that I had then gone to work for had, you know, had become a lot bigger than it was. And I had sort of now was starting to feel like things were the same as they were in the, in the prior role. And it was like, that's my cue. This isn't, this isn't me. I need to go back to something where I have more control. And where my ability to be inventive and pivot and just, you know, kind of drive stuff and move very quickly is something that I'm actually rewarded for as opposed to. Working for a really big company where that's sort of like encouraged less and less. And so I figured, you know, if I do this and it fails, then….
LJR: You've been there before.
JH: I can get another job.
LJR: Yeah, yeah. You've, you've seen that I've this before, right? So we're back to the startup land and [JH: Yep.] And I'm wondering now, what does risk feel like to you? What is risk?
JH: The funny thing is that I…Everything that's gotten me to here has taught me, you know, risk is just something to be managed or mitigated, and it's just, it's never like the kind of cliff that you feel like it might be as long as you're sort of thinking through like where the path is and what the options are. And so I don't think about things in terms of taking risks so much. Like even in making this, this transition, what would've, you know, 15 years ago have seemed like you know, I don't know that I'm ready to do this. It seems like very nerve-wracking. I sort of jumped into this faster than anyone expected. I mean, I probably didn't even, you know, give it the sort of due diligence that I needed because I basically felt like, look, I trust my gut instincts and I know that I've had the ability to land on my feet. So the concept of risk is, is just not as scary as it once was.
LJR: Yeah. Jamie, I don't know if you recognized you did this, and I'm not sure actually if you were trying to remember what Alice Water said and use her words verbatim or if you were kind of giving the thought back of what she said, but if, if you were just going on feel to say that she thought this was awesome and this was excellent and it was delectable, the first thing you said was this pastry or this…this is dangerous. And ‘dangerous’ was the word you used to say. This was the best thing. I think there's, there's something there. You need a little of that danger for it to be tasty and exciting and interesting and good. And it seems like that's a part of who you are. And yes, risk can be mitigated a bit and all. Also can be heady and what keeps you in the game? Certainly I would say, jumping into motherhood with both feet the way you did. Huge, huge risk, but huge reward and I think it's brilliant. So I'm excited to see where this is gonna take you. The next risks are not gonna feel that way or will or whatever, but they're they're certainly gonna be out there for you and I hope you grab them. So thanks so much for sharing this.
JH: I really appreciate it.
LJR: That was Jamie Hansen, an experienced solutions leader currently working to help a startup in the procurement space, Zip, move to the next level. She has worked at companies large—including Salesforce—and small—including her own wholesale bakery business. She lives in the San Diego area with her twin girls, living it up by the water and basking in the sunshine.
We are living it up this summer with lots of great episodes, so wherever your adventures take you, keep tuning in each week with me, Leslie Jennings Rowley, on Roads Taken.