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The Career Flipper Podcast artwork

From product manager at Amazon to startup founder, meet Jane Dashevsky

The Career Flipper Podcast · 2025-10-09 · 42 min

0:00--:--

Key moments - from our scoring

Substance score

45 / 100

Five dimensions, 20 points each

Insight Density9 / 20
Originality7 / 20
Guest Caliber11 / 20
Specificity & Evidence8 / 20
Conversational Craft10 / 20

Jane Daszewski's career transition from a decade-long tenure at Amazon to founding The Starter Set offers a masterclass in entrepreneurial decision-making that goes beyond typical startup origin stories. Unlike many founders fleeing burnout, Jane actually loved her product management role, her team, and the company culture - but carried an entrepreneurial spark that eventually became impossible to ignore. Her idea emerged from lived pain: midnight research sessions trying to navigate overwhelming product options for her two young children, which she validated through a survey revealing 90% of parents found product research painful. The episode dives into her thought experiments for the decision ("which path would I regret least?"), her financial safety net with her husband's support, and the bittersweet emotions of leaving. Now eight months in, she's repurposing skills from her background in product management, marketing, and even her undergraduate degree in journalism to build content (including a podcast called "Getting Started With Baby" and blog content) while developing the core product. She emphasizes finding a co-founder for distribution potential and speaks candidly about the ongoing self-doubt despite taking the leap.

Key takeaways

  • →Leaving a job you actually enjoy is possible if an entrepreneurial vision feels more fulfilling long-term - frame decisions as "which will I regret least" rather than seeking certainty about "right" choices.
  • →Validate startup ideas through direct customer research before quitting: Jane's survey of parent friends yielded 90% validation that product research was painful, justifying her leap.
  • →Repurpose existing skills from previous careers strategically - Jane's product background, marketing experience, and journalism degree all feed her content strategy and product thinking simultaneously.
  • →Co-founder selection is a critical early step that increases the likelihood of actually shipping the product to market, beyond just proving personal feasibility.
  • →Building in public and creating adjacent content (blogs, podcasts) can serve both customer education and business validation during the early stages of product development.

In this episode

  1. 1Jane's background: 10 years at Amazon as a product manager
  2. 2The spark: identifying the pain point of baby product shopping
  3. 3The decision: wrestling with leaving stability for entrepreneurship
  4. 4Taking the leap: resigning and finding a co-founder
  5. 5Building The Starter Set: an AI-powered baby registry service
  6. 6Repurposing skills: from tech expertise to journalism and content creation
  7. 7Eight months in: the messy middle of startup life

Mentioned

AmazonThe Starter SetDwellspringJane DaszewskiJenny Dempsey

Guests

Jane Daszewski

Topics in this episode

The Starter SetAmazon product managementAI-backed servicebaby registriespersonalization in retailproduct researchco-founder selectionparenting content marketingGetting Started With Baby podcastthestarterset.com blog

Questions this episode answers

What problem does The Starter Set solve?

The Starter Set uses AI to help parents find personalized baby products and navigate overwhelmingly large product registries (typically 80+ products), solving the analysis paralysis and midnight research sessions many parents face when shopping for their children.

How did Jane validate the need for The Starter Set before quitting her job?

Jane created a survey and sent it to parent friends and her mom group, asking about pain points in baby product research; 90% reported that research was a very painful part of their parenting preparation.

How long has Jane been working on The Starter Set?

Jane has been working on The Starter Set formally for about eight months, after spending a couple of months finding a co-founder and conceptualizing the product.

What was Jane's career path before Amazon?

Before her 10-year tenure in product management, Jane switched careers every two years, earned an MBA with a dual degree in tech, worked in marketing roles, and started her career as an editor at a magazine with a journalism bachelor's degree.

What content is Jane creating alongside The Starter Set product?

Jane is creating a blog at thestarterset.com and a podcast called "Getting Started With Baby" where she interviews parenting experts like sleep coaches, OB-GYNs, and other parents, drawing on her journalism background.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

9 / 20

The episode contains modest insight density with some useful frameworks (the 'regret least' decision-making model, thinking of entrepreneurship as educational investment, understanding the repurposing of career skills) but relies heavily on narrative and emotional processing rather than novel operational advice. Most substance is personality-driven reflection rather than actionable, non-obvious principles that a B2B operator would extract.

Well, I'll answer it in a couple of ways, but one, uh, I don't know, depending on your personality and mine is like this. I don't know that you ever, like, know that something is the right decision, right? Like, until later down the road, sometimes you're like, which decision will I be more comfortable living with?
I think about it like to me it's like as if I'm going back and creating like an educational opportunity for myself. And so I'm like, well, I think, you know, whatever, two years into my mba, like I'm willing to put, not sank, but like I put two years into an MBA and I'm willing to think about it in the same way

Originality

7 / 20

The episode recycles well-worn startup and career-change narratives: the passion-project origin story, the supportive spouse enabler, the 'follow your dream' arc, and the emotional vulnerability confessional. While Jane's specific situation (Amazon PM leaving to solve parenting products) is particular, the frameworks and meta-insights are standard career-pivot content. Little first-principles thinking or contrarian positioning.

I'd been at my company for 10 years, and I loved what I was doing, and I loved who I was working with. But in the back of my mind, I'd always wanted to do my own thing.
sometimes you gotta do the thing that you're scared of because that's the thing that makes you grow

Guest Caliber

11 / 20

Jane is a legitimate practitioner (10 years at Amazon in product, now 8 months into her own venture) with credible operational experience, not a career coach or thought leader. However, she is only 8 months into founding and has no revenue, proven traction, or meaningful scale to show. She's relatable and honest but not yet someone who has definitively 'done the thing' at commercial scale. A solid mid-tier guest for a career pivot show, not exceptional for a B2B operations podcast.

I'd been at my company for 10 years, and I loved what I was doing
I've formally been at it for eight months.

Specificity & Evidence

8 / 20

The episode includes some concrete details (8 months into founding, 2-4 year expected runway, 40 hours to complete a baby registry, finding a co-founder took a couple months, launching within 'couple of months') but mostly stays at high abstraction. No revenue figures, user feedback data, market size, or specific product metrics. The 90% pain point finding from survey is mentioned but not interrogated. Lacks the granular evidence that would make claims testable.

90% of parents were saying that research was a very painful part of their parenting prep
it can take, you know, upwards of 40 hours just to do a baby registry

Conversational Craft

10 / 20

The host asks warm, open-ended questions and creates safe space for Jane's emotional honesty, which works for a personal narrative podcast. However, there are few challenging follow-ups, minimal pushback on claims (e.g., the 90% stat, the market size, unit economics, competitive landscape), and no sharp interrogation of Jane's assumptions. The conversation is friendly and encouraging but lacks the intellectual rigor needed for substantive B2B learning. Questions are mostly supportive rather than probing.

And I want to jump back to something about being right, because you're so right, you're so right that there is no way to know until you do it.
Yeah, that is a great perspective to have on it. And just to do it like you're doing it, you're taking the steps.

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker A56%
  • Speaker C32%
  • Speaker B11%

Most-used words

career17back16jane16decision15product14kids13feel13building12part12felt12trying11founder11parents10help10sometimes10podcast9

Episode notes

What happens when you spend 10 years at Amazon, love your job, love your team and then parenthood shakes everything up? That’s the story of Jane Dashevsky . Becoming a mom of two under two made her start asking the big questions: What do I really want for myself? For my family? That entrepreneurial spark she’d carried deep down finally pushed her to walk away from stability and build something of her own. Jane is now the founder of The Starter Set , an AI-powered service that helps parents cut through the chaos of baby product shopping. Because let’s be honest, the last thing overwhelmed parents need is another late-night Google spiral about strollers. In this episode, Jane gets real about: Leaving a steady job after a decade at Amazon The identity shift that comes with walking away from stability Parenting while building a startup (the real messy middle) Testing ideas piece by piece and finding her way in Seattle’s startup world How to not let numbers or social media dictate your worth This is a conversation about courage, resilience, and choosing yourself, and your family, even when the path ahead is messy and unclear. Listen now and

Full transcript

42 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: I'd been at my company for 10 years, and I loved what I was doing, and I loved who I was working with. But in the back of my mind, I'd always wanted to do my own thing. But, like, it was probably my hardest career decision ever.

Speaker B: Hello, and welcome to the Career Flipper podcast. This podcast, uh, is really just me handing you a, uh, big old permission slip to chuck the rulebook out the window and rethink your entire career. You know, um, just an average day. I'm Jenny Dempsey, host of this show, Furniture Flipper. And yes, after two years post layoff, I'm back in the corporate world again. Well, I like to call the investor

Speaker C: in my dreams, because I can't go

Speaker B: back to working how I used to work. And this job keeps the lights on while I happily and messily build my furniture flipping business on the side. And for that, I'm so grateful.

Speaker C: In today's episode, you'll get to meet

Speaker B: Jane Daszewski from Seattle, Washington. Jane spent 10 years at Amazon M. Yeah, 10 years of building, building her career, loving her work, loving her team. And then, well, um, she became a parent. Two kids under two, that changes things. Or so I've heard.

Speaker C: And she started asking herself the big questions.

Speaker B: Where do I see myself long term? What do I do with all these business ideas in my head that I keep sharing with my husband? What do I really want for my family, for myself? And that entrepreneurial spark she'd always carried deep down got louder and louder until she finally made the decision to walk away from that steady paycheck and start something of her own. But it's not just anything that she started. She created the Starter Set, a service

Speaker C: that uses AI to cut through the chaos of baby product shopping.

Speaker B: Because, let's be honest, from what I hear from my friends that are parents, finding the right stuff from your kids is really overwhelming. It's exhausting. And honestly, it's just not the thing that you have time or brain space for. And Jane knew this from experience, and her dream was to make this whole process easier. And what I love about Jane in this episode is how real she is about the messy middle. She doesn't sugarcoat it, and she's in the thick of it right now. She just kicked this off eight months ago. And being so honest about the emotional rollercoaster of entrepreneurship, um, this conversation is about dreams and courage and resilience and choosing yourself and your family, even when the path ahead is messy and unclear,

Speaker C: even when you doubt yourself.

Speaker B: I think you're really going to Connect with Jean's story. Let's get into the episode now.

Speaker C: We go way back. I mean, we're talking like, what was it, 15 years? I think I calculated that correctly.

Speaker A: I can't count that high. Don't ask me.

Speaker C: Yeah. And as we were talking before, I was like, yeah, that kind of just feels like, I don't know, last week or something. So what is time? But anyways, Jane, thank you for being here on the Career Flipper. I am really excited for everyone to meet you and also just selfishly excited to chat with you again and love that our paths have reconnected after so many years. Tell everybody about you, who you are and where you are and what you're doing right now. And then we're going to dive into all the juicy stuff because there's some good stuff here.

Speaker A: Well, I'm super excited to be here and yeah, it's wild, uh, that we've been able to reconnect and um, but to introduce myself, I'm Jane Daszewski and right now I'm in the process of building a new service for parents called the Starter Set. And what it is, is it is an AI backed service that helps parents and families find just the right things for their children at the right time, personalized for their families. And I'm a mom of two. I have two kids. Two, uh, and a half and a four. I'm always like, how old are they now? But anyway, I have two small kids and you know, there's just so much mental burden that comes with having kids and you're constantly thinking about like, what they need next and trying to sort through all the stuff. And you know, you go on Amazon or Target or whatever, Walmart, any store, and there's just so many options and you're just left with this like, analysis paralysis feeling. Um, and so the goal was obviously we've been able to figure out personalization for social media and there's some personalization certainly in retail, but I thought how great would it be to have a service that really understood you and could help you pick the stuff that you needed for your kids. And so, uh, that is what I'm building. I have a co founder and we're working as hard as we can to get something out. And starting with baby registries, because those are 80 products deep. So wow.

Speaker C: I mean that's incredibly like the, the thought that went into this to not only like help other families, but like, it, it sounds like it came from a very important place in your life of like, I don't Know what I need, so why don't I figure it out? But how did this all begin? Obviously, you know, having kids and diving into parenthood. But the career part, like, how did this begin? How did your career start? How did you flip into this, Jane?

Speaker A: Yeah, well, actually, for me, it was at the time I was working in, like, a high pressure tech job and, you know, had two kids and was trying to figure out how to balance all of that. And I was finding myself, like, after the day was done and the kids were asleep and, like, you know, having been able to spend some time with my husband, et cetera, like, it would be midnight, and then I'd be like, oh, I have to go order something. Or, like, you know, I just noticed my son is, like, starting to walk. Maybe I need to, like, think about that and do I need anything for him? And. And so I would be doing research at midnight and, like, looking at blogs and looking across retail sites and maybe, like, looking at an influencer or two. And it just felt like such a bad use of my time, you know, like, at midnight. Like, that just didn't feel good. Yeah, yeah, it was exhausting. And so, uh, even just the part of, like, oh, he grew out of his clothes, and I need to, like, think about that again. You know what I mean? Like, just another thing on the list. And so it occurred to me that, like, this was probably a problem that needed some solving. And so I created a survey. You know, my background was in product, and, you know, I had some training in marketing. And so, like, naturally I was like, do other people have this problem? And let's go talk to some potential customers. And so, um, created a survey, sent it out to, you know, parent friends. I'd been part of a mom group, sent it out to the mom group and just asked people, like, where their pain points were, you know, if they were spending time on this. And it came back that, like, uh, 90% of parents were saying that research was a very painful part of their parenting prep. And so it just felt like a problem that was worth solving. Um, and because I had experience in product from my previous work, I felt like I could kind of see and get my hands around how to solve it. And so then it was just a question of, like, am I going all in on this? Like, does it make sense to do that? Should I go all in on this? And that's when the questioning process starts, obviously, when you make those big career decisions. I'd been at my company for 10 years, and I loved what I was doing, and I loved who I was working with, but in the back of my mind, I'd always wanted to do my own thing, but it was probably my hardest career decision ever.

Speaker C: Yeah, that's. That's a huge pivot from going from the safety and security of a stable job that you've had for over a decade with colleagues that you actually enjoy being around and, uh, work that you enjoy doing. And then to know that there's this entrepreneur, entrepreneurial spirit kind of buried down deep. And I'm. I'm kind of curious because I think a lot of us. Well, at least you and me, we feel this way. And people listening probably can relate to this. There's a. There's sometimes that spark that's buried below, and we feel it, but we just like, okay, no, no, no. I gotta keep the stable job. I gotta keep the traditional path. I gotta, like, you know, I. I have kids. I gotta make sure that there's a paycheck coming in. But what was it about that. That feeling that you had of wanting to do something on your own that made that feel. And I'm going to say this. Uh, the cost of staying may have been more than the cost of going type of thing where. When did you know that it was the right decision to go out and do your own thing versus staying in that kind of stability, you know?

Speaker A: Yeah. Well, I'll answer it in a couple of ways, but one, uh, I don't know, depending on your personality and mine is like this. I don't know that you ever, like, know that something is the right decision, right? Like, until later down the road, sometimes you're like, which decision will I be more comfortable living with? But, like, using the term right is so loaded and it's so hard. And like, sometimes even now, I'm like, did I make the right decision? What's the right decision? Am I doing the right thing? You know what I mean? Um. And so, I don't know. I don't know that you ever get the sense of, like, there's a right. I don't. Well, I actually don't know if in life there are, like, right answers, right? There's just different options. And so, like, the way that I thought about it was a couple of things. Like, I, you know, it was a hard decision. And so there were, like, a couple of thought experiments I was doing with myself to try to figure out what I wanted to do. And, you know, one of them was, like, I like to think about, like, which path would I regret least? Right? And, like, which thing would I be most proud of, not to say that, like, what I was doing at my work, I wasn't proud of. I was. But, like, you know, if I looked back on my life from, I don't know, 80 or whatever, which thing would I be most excited to tell someone I accomplished? And for me, it had always been my dream to do my own business, to be able to grow something from the ground up. Um, and so, you know, I felt like I had to take that chance. I'd been, uh, in a job for a decade, right? Like, that'd been the longest I'd ever been anywhere. And it was longer than I ever imagined myself being there, which is a testament to how great it was. But, um, you know, I just really needed to think about, like, ultimately, in the fullness of time, like, what would be most fulfilling, what would I be excited to tell my kids about, what would I be excited to look back on? So there was that frame. Ah, you know, I was also really fortunate to be in a position career wise where I could take a step back. Like, uh, I, you know, between myself and my husband, we could do it in a financially safe way. Even though sometimes that's still panic inducing, but, you know, you know, we could do it. Um, and my husband was very supportive because he'd also known that it was my dream. Like, he'd heard me rattle off thousands of business ideas over the years. Maybe not thousands, I like to exaggerate. But, um, so there was that. And then I remembered actually getting career advice from senior leaders at my previous company. And I remember one of them saying something like, sometimes you gotta do the thing that you're scared of because that's the thing that makes you grow. And that was also something that I thought about because at my last company, I'd been in kind of the team and the position I was in for eight years of the 10. And I knew it really well. I felt really comfortable, even though there was always something to grow and stretch into. But I felt pretty confident and it felt like it was time to push myself into something that was scary and uncomfortable. And boy, it has been. That just.

Speaker C: That makes so much sense. And I want to jump back to something about being right, because you're so right, you're so right that there is no way to know until you do it. And then years later, you have the kind of perspective to be able to look back and be like, oh, yeah, that was the right choice, or, oh, no, it was, but you just don't know. And to really just take that chance which it sounds like you. We're like, this is it. Like, this is where I'm going to grow. This is where I'm going to be able to help others. This is where I'm going to be able to help myself. Not have these, you know, midnight, uh, search parties where I'm looking for, um.

Speaker A: I wouldn't call them a party.

Speaker C: Yeah, there's. There's.

Speaker A: Yes.

Speaker C: Confetti here. There's no cake. Well, maybe. I don't know. But, uh. But you really leaned into that, and I think that's incredibly important to note for so many people who are, like, on the edge of, like, do I do it or not? You don't know if it's going to be right. And there is no right. So just erase that completely. And what was it like when you put in your notice that you were leaving? What was that. What was that like for you? Can you talk about that until.

Speaker A: Oh, my gosh. I don't know. I feel like it was like a breakup. You know what I mean? Like, you know, I feel embarrassed about this, but whatever, you know, you, like, put so much of yourself into work, right? Depending on who you are. I certainly do. I can't do things even 80% of the way. Like, I go 150. And so, like, I'd put myself into that work. Um, and it becomes, like, a part of your identity. And, like, you know, you see people you work with more than you see your family, really. Um, and, you know, the kind of job I was into, it was like, you could be on, really, at any hour. Right. Because if somebody needed something or there was an email flying around, whatever it is, I mean, that's just our work culture sometimes in the U.S. but, uh, so it was really hard. And I'd been there so long. Um, and it felt like, you know, the beginning of something, but also the end of something. And it was different because I wasn't going to a secure next job. Uh, so that also felt really hard because it was like, I was going. I wasn't sure I was making the right decision, quote, unquote. I felt a little uncertain. Um, so it was bittersweet, I would say. Like, it was exciting to, like, have made that step toward a dream that I've had. And hopefully it all pans out. Remains to be seen, I guess. Um, but it was also super hard, you know, and. Yeah, there were tears shed.

Speaker C: Yeah. Yeah. And. And I appreciate you sharing that. I know that's like a. That's a really pivotal moment and very personal moment, and I Think, you know, a lot of people who are on the podcast and talk about flipping their careers are doing it because they don't like their jobs, they're burnt out or whatever. But this is a very different scenario where you did like it. It was a good job, you enjoyed it, you liked who you are. And so I really want to emphasize that for anyone listening, because whether you like your job or not, you can still make these decisions, whether or not, you know, it's the right decision. But if it feels authentic to you, then it sounds like that might be the direction you need to go. Whatever is pushing you forward. And for you, there was more of a calling of like, I want to start something on my own. I've had this thought in my mind for, you know, years, and now you're doing it. And I bet, I mean, maybe you heard feedback, but I bet some other people, when you put in that notice, were like, ooh, if Jane can do it, I. Maybe I can. And, like, maybe that, like, you know, inspired other people on your team, but I just think it's a big, bold decision to put in that. And then you leaped into it. And I think what's so cool about having you on, too, is that you are in the middle of this right now. So it's not like you just. You did this 10 years ago, and you've been doing this for a while. Like, Jane, like, how long have you been at this right now?

Speaker A: Um, well, I've been at it, I guess, formally for about eight months. I want to say eight.

Speaker C: Okay.

Speaker A: Uh, but part of it was just, like, seeing if I could make something that even feasibly addressed what I was interested in doing. Uh, and then part of it was, like, I was really convinced that, um, for me, in this journey, it was super important to have a co founder, and that one of the things I think about, too, is that it's not just about whether I can personally be successful or not be successful. Like, I feel very strongly that this product service idea should be out in the world. Like, however that happens, it should be out in the world. Because this, like, finding stuff for your kids and just retail shopping in general is so painful and so unnecessarily painful. And it feels like the pendulum swung very deeply from the days of mom and pop shops on the corner that didn't have enough selection to overwhelming amounts of selection, to not being able to even understand what you need. And so, to me, it feels like this thing needs to be out in the world. And so when I think about that, I'M like, well, what can give me the greatest chance of it really being out in the world? And I knew for me, that was a co founder. So, uh, I went through the process of looking for a co founder.

Speaker C: Ah.

Speaker A: And that took me a couple months. M. I went through the process of trying to take this thing that was in my head, and I'm not visual at all. So finding someone who could help me visualize it and design an experience, because that could also help make it more real as well. Um, and so there were kind of steps along the way, but I've formally been at it for eight months.

Speaker B: You know those nights when it's late, you're wiped out, but your brain is like, yeah, nope, we're staying up. Or the afternoons when you have so much to do and you really want to focus, but the distractions and the to do list in your head just will not stop.

Speaker C: Yeah, I get it.

Speaker B: I'm right there with you. That's why I wanted to share something that I've been using. It's called the Dwellspring mobile app. It puts over 300 professionally engineered soundscapes in your pocket that are helping over 1.3 million people every week to achieve restful sleep, mindful presence, and productive flow. And I'm one of them. You can create your own mixes from scratch, generate custom noise colors like white or brown or pink. Even build your own binaural beats. All available offline without an Internet connection. And always ad and interruption free. And a fun fact, dwellspring actually started as a podcast. A tired dad was just trying to get his newborn to sleep, and now that show has over 300 million downloads. The app takes what worked there and makes it even more customizable for you in your busy life. If you want to check it out, download the app dwellspring like Wellspring with a D on the Apple App Store or Google Play. And if you use the promo code Flipper, you'll get a free month of premium. That's D, W, E, L, L, S, P, R, I, N, G. Promo code Flipper for a free month of premium. Dwell. Spring. Reclaim your rest. Now let's get back to the episode with Jane.

Speaker C: Eight months. I think a lot of people can relate to that. So you put in your notice, you left your job, and here you are. It's been eight months and you're going at it and you f. You took you two months to find the the right co founder and you're doing it.

Speaker A: And maybe more than two months. I don't remember. Yeah, I don't remember a couple months.

Speaker C: It's a blur. It's all a blur.

Speaker A: Yeah, it is a blur.

Speaker C: I think this is. I mean, uh, okay, I'm. This might seem like I'm. I'm switching gears here a little bit, but one of the things that really stands out to me that you are doing is that the repurposing of your skills, Jane. Like, you had this job for 10 years, and all of the things that led up to that job before, that job in your career path, like the skills that you built, whether it's product marketing, all the things and tech that you worked in, you're essentially repurposing them for this and obviously learning a lot more new things. But you knew what to look for in a co founder because you've worked on teams before and you knew what you needed. You knew what you needed to build because you've worked in tech before. And I love that because sometimes when we take these leaps and we're like, okay, what are we doing? We think we're starting from scratch, but we really have so many important skills from our experience, and we're not just doing this completely blind, even if it is in a completely different industry. So I'm curious, can you speak to a little bit of the repurposing of skills that you have that you're finding that you're using now all the time, and that you're like, oh, I did this before and it feels maybe a little familiar. And then maybe some of the ones that you're learning, like, can you just touch on that a bit? Because I think it's a common theme for people to leap and they're like, ah, uh, what am I doing? Well, you actually do know more about what you're doing than you think.

Speaker A: Yeah, I think that's like a super valuable point. You know what I mean? Like, it's just because I don't. I've actually felt this. So prior to being, uh, in my previous job for 10 years, I'd actually switched not just jobs, but careers every two years.

Speaker C: Sounds about right for tech. Yeah.

Speaker A: Uh, ah. And when I went into product and tech, I had zero. I had gone and gotten an MBA and, uh, a dual degree with an MBA and a tech degree. But I didn't even know product management was a job. Like, I remember coming into my first day at my old company and, like, my manager there asking me to do a roadmap, and I had 0, 0, which is like a basic product skill. So, you know, like, organize what we're going to work on, right? Like, just basic product skill. No idea what that was. Like, not a clue.

Speaker C: Yeah.

Speaker A: Anyway, but my point is. I digress. My point is that what's interesting in every career step that you take is these layers of things that all these experiences you've had that you build on. Something that I've found really fun about this new step is in this space that I'm in, which is parents, moms, expecting moms, it's super important to actually create not just a useful service, and we're in the process of building that, but also useful content. Because most moms are looking to their friends for advice. They're using social media, they're following content that they like. Um, and some of my previous jobs were actually marketing, uh, through creating content. And my bachelor's degree was in journalism. And my first job out of college was as an editor for a magazine. And so what's super interesting is, like, right now, uh, while we're in the process of building, where I'm using the skills that I had from product and tech and working with an engineering team and all of that, I also am weirdly leaning back into all my journalism skills. Right. Because part of what I'm doing is creating content for moms. We have a blog on thestarter set.com and inspired by youy Partially. No way. Yeah, Inspired by youy Partially. We also have a podcast, um, which is called Getting Started With Baby. And in that, like, I'm interviewing all sorts of parenting voices, whether they're sleep coaches or OB GYNs or other moms. Um, m. And, like, that leans back into the journalism skills. So it's like this really interesting tapestry of all the stuff that you've done before. Right. You just don't know how random skills are going to impact you. And the other thing that I've been doing, which I'm generally terrified of, is, you know, so part of what you do when you have a startup and you're potentially seeking funding or incubation or support, is you go and you, like, start pitching, which means you're speaking in front of a bunch of people and, you know, trying to seem charismatic and like, you have it together. Um, and like, I hadn't done that since my MBA program because in my previous company, that wasn't, like, we didn't really present, like, that. We presented more, you know, in the written form. And so I hadn't had to do that in quite some time. Um, but I was leaning back into what I'd learned in my MBA program. Like, to talk louder than seems natural, you know what I mean? Because it, uh, makes you sound more excited and like, I don't know, weirdly gets rid of your nerves. But, uh, anyway, so, yeah, you just pick up stuff from everywhere that.

Speaker C: Exactly. That was so well said. And the word tapestry that you use I think really captures that so well. It is these, all these things woven together and you don't know how they're going to show up or when they're going to show up or how you're going to be able to repurpose them for whatever new path in life, whether it's a career, a hobby or just, I don't know, daily living, like, you just don't know. And so having those there and knowing that you're not starting from scratch, you do have a lot to build upon. And so. So you took the leap and you're in it. And where are you now, like, as far as building it goes? What's like a day to day like for you now? Like, because you're, you're working remote at home, right. So you're with your kids and so you're also doing.

Speaker A: They're thankfully in daycare.

Speaker C: There we go. And like, what is a normal day like for you as you kind of work through this and build this?

Speaker A: Yeah. So I mean it, the nice thing is it can be varied. Uh, I have time to kind of like dig in and pursue things that I'm like, trying to get better at or interested in or whatever. But most days include me trying to figure out Instagram, which is not a natural. It's not natural for me. Uh, so there's that somewhat painful journey and you know, creating, uh, content, looking for guests for the podcast because we're kind of doing parallel tracks between me and my co founder right now and like some collaboration. So on the one hand we're working on kind of building up the content and marketing and community side of what we're doing as we're building actively. On the other end, I'm working really closely with my co founder who's uh, responsible for the engineering portion of what we're doing. Uh, creating requirements, reviewing how the results are looking so far, planning for testing and beta with, uh, customers or potential customers. Um, there's that part occasionally, um, it's looking through the startup community. I'm in the Seattle area, so the startup community in the Seattle area to figure out is there an event I should be a part of, should I be doing a pitch, should I be talking to someone, um, going to some startup meetups and things like that. It can be varied.

Speaker C: It keeps you on your toes and you're busy and you're constantly in the exploration phase and testing phase. And you know, let's say a year from now, where do you see yourself and your co founder at? Like, where, where's the vision going? Like, if you were like we were talking this time next year, like, what would you be saying?

Speaker A: Uh, well, within a year, oh boy, there better be a live product. Um, so, you know, we're hoping to have a live product end to end product available for customers in the next couple of months. We should be ready to start testing in the next few weeks. Um, and the goal is to see how customers respond and to really help. We're starting by creating a fully customized personalized baby registry. The goal with that is that we can help expecting parents get through their baby registry phase with much less stress, with much less research. Like there's this mind boggling statistic that it can take, you know, upwards of 40 hours just to do a baby registry. Like, that's nuts. You know what I mean? It's crazy, isn't it? Yeah. I mean, so there's that, I mean that there's like 80 plus products you're looking through that, like many of them you've never even heard of. Like, I'm trying to think of one where I was like, what on earth is that thing? I don't know. Still some parents, I'll be like, have you heard of a white warmer? They don't know what that is. There's just stuff that if you haven't gone through it, even if you're going through it a second time or third time or whatever, it's just a learning curve all the time. The goal is within a year that we're actually actively able to help parents reduce that research burden and decision fatigue.

Speaker C: Yeah, the hours that you're going to save people, um, I didn't realize that's how much work went into a registry. Will say as an auntie or, you know, especially auntie to whether my actual family or friends, kiddos. Looking at these registries, I don't even know what to pick. I always am, like, what would I. What's the best thing I could get for them? I don't know. Half of these things are. And if I get clothes, like, is that going to be helpful? Like, so even like looking at it from the other angle of like, if I could look at a registry as an ant and know that this is actually going to help them, that saves me time and stress, too, of like, buying this. And so it's kind of like this across the board, supporting families in a way where they're actually going to get the things that they need, um, and be able to use. Because it also seems like every day there's some new, uh, kid product out there.

Speaker A: Yeah.

Speaker C: Something or other. And, I mean, what did you say? A wipe warmer? Like what? Like.

Speaker A: Yeah, because I heard of that. I mean, it's just. Yeah, well. And some of the stuff is like, you don't actually need it, but you don't know that you don't need it. I mean, it's just really hard. Like, I've had friends who told me that they were so overwhelmed, they opted out. They had their husbands look at it. They were like, can't do it. You know what I mean? Uh, it is very overwhelming.

Speaker C: Yeah, it is. It's a lot. It's a lot. And you're doing something to solve this and you're in it and, you know, on your own career path, you're building it and you're taking that leap. Do you have a time frame that you're like, if this isn't done by X, then you are reevaluating different things? Obviously, that's not going to be the case. But I think sometimes when people leap into these, we build this in our mind of like, I'm going to give it a year, or I'm going to give it five years or whatever it is. You know, maybe how much savings do you have? Like, I'm just curious if that is something that applies at this point. Or you're just like, I'm all in. There's no other option?

Speaker A: Uh, no. I feel like there was some. I don't know, maybe it was a quote from Bezos, Jeff Bezos, or something about how you have to both, as a founder, you have to both be optimistic that it's going to succeed, but also realistic that 90% of the time these things fail. So it's hard to hold that duality in your head. M. And that's part of the challenge of doing something like this. But, uh, yes, of course, I have Gates on. Does this make sense? I think I am, um, sort of waiting to see, like, we've broken it down. So, like, the idea is that we want to build for phases past the baby registry, but we've broken it down to, like, let's release one thing and see how it does and see how it helps parents and see where we take it from there. If that doesn't resonate with Parents and certainly we're doing research along the way to convince ourselves that this makes sense to put time into. But if it ends up not resonating or whatever, I mean, that's certainly a big signal and that's not necessarily time bound. Although we want to make sure we have something that's achievable to build within six months, a year, whatever it is. And then for me, all in time wise, it feels like I need to get to some sort of financial solvency within, I don't know, maybe a two year window or something like that. I think about it like to me it's like as if I'm going back and creating like an educational opportunity for myself. And so I'm like, well, I think, you know, whatever, two years into my mba, like I'm willing to put, not sank, but like I put two years into an MBA and I'm willing to think about it in the same way in the sense that this is like a journey of like learning a whole bunch of new skills, having different experiences and I'm willing to think about it in that same light.

Speaker C: Yeah, that is a great perspective to have on it. And just to do it like you're doing it, you're taking the steps. And I'm really curious, Jane, of, you know, from what you're learning about just going for it and building in these gates and just, you know, testing everything out, experimenting, having the plans and structure and strategy that you're building for someone listening right now who might be in their job and maybe they love it, maybe they don't, but they feel that same feeling you felt. I want to do something on my own one day. Do you have a piece of advice for them that might guide them on how to really be okay with that decision, that it's okay to want to do something on your own one day. What would you say to that person?

Speaker A: I mean, I guess I would say two things, which is one, like listen, you only live once, do the things that you feel like are exciting to you. But like also, you know, my husband at some point when I was trying to like make this decision, would always say things like, you gotta like treat life more like a video game, sometimes, like take it a little less seriously, like if this doesn't work out, you'll do something else, whatever. And sometimes it's hard to have that perspective. So one decide what matters to you in life and whether you want to pursue something, what you'll regret least, etc. The other thing is really deeply know yourself. You know what I Mean, take stock of yourself and your uh, emotional bandwidth. Because if you do this, uh, for most people, success will not be overnight. Uh, you will have many, many moments of doubt. Like many figure uh, out the things that pull you out of the troughs. You know what I mean? My husband likes to make fun of me because I'm like a roller coaster, like peak trough, peak trough. Luckily, I think my co founder is more even killed, but I'm not. And so I've had to think about like, what are those things that will get me through a day when I'm feeling like, what have I, like, am I doing anything? Is this going anywhere? Am I yelling into a void? You know what I mean? Uh, it might be something like take yourself out to lunch that day, you know what I mean? Or uh, I got myself these um, affirmation cards and I like pull one out every day and it'll say things like, you know, you're living your best life or whatever. I don't know, something to like recenter me outside of my own head. And whatever it is, that's not what will work for everybody. But like, you got to know yourself well enough to know like if faced with this, like, are you going to be able to weather the extreme uncertainty and the weight and the not knowing if it will succeed and the trying to take positive and trying to take small signals from the universe, even if you're not sure if you're on the right track. So, uh, know what you want out of life and know yourself. I would sum it up as that.

Speaker C: That is really great, like just such real advice. I mean it's so true. The storms are no joke. And the self doubt, you know, when you're not sure exactly what you're doing, it's gonna like crush you at some points. And yeah, it's like, what do you do then? Can you weather that? Because this thing that you're creating needs you to be able to weather that in order to grow and move forward. And you're doing it. You're freaking doing it, Jane. And you're setting the example to all of us. And the fact that you're like in it right now is just, it's really inspiring because I think a lot of the people I talk with are folks who have done it and they're, you know, past it. And it's like, but wait these moments when we're in it because uh, girl, I'm right there with you. I'm in the middle of it too. And I am like figuring this out and I'm like, all right, I don't know what's next, but I'm going to try this and keep going. And yeah, I appreciate you sharing all of this with us. And I'm so curious too. Like if people want to get involved with some of the testing or they want to learn more about the starter set, listen to the podcast, read the blog. Where can they connect with you? How can they find you? Where are all the places to go?

Speaker A: Yeah, I would love that if they'd like to connect with us. Um, I would say if they're interested in signing up or testing or getting the latest on what's going on with us, uh, go to thestarterset.com we have a sign up list there. Um, and that's also where our blog is. Um, if they're interested in hearing more about the parenting experience or from parenting, uh, voices from across the spectrum, they can find us on Getting Started with Baby. Uh, that's a podcast that's available. Spotify, Apple, YouTube, uh, and also can be found on our site. Um, then also we're on Instagram hestarter set. So uh, feel free to follow us there as well.

Speaker C: Absolutely. This is great. And everything will be in the show notes. I hope people connect with you. Jane, thank you so much again. I love this chat. I loved connecting with you and just so glad we kept in touch over all these years.

Speaker A: Me too. Thank you so much for having me. It was super fun.

Speaker B: Thanks for hanging out with me and Jane on this episode of the Career Flipper podcast. You'll find all the ways to connect with Jane in the show notes. And if this conversation lit even the tiniest spark or made you feel a little less like you're out here flailing at it alone, the best way to keep this energy going is to hit follow, drop a review and send this to a friend who's also mid career.

Speaker C: Plot twist.

Speaker B: That's how we grow this messy, magical little corner of our flippin community. At the end of the day, here's what I want you to remember. You're not behind, you're not broken. And you are definitely not too late. Starting again is always on the table. And that first tiny step might feel terrifying. You might ugly cry through it. But it could be the step that will change everything. So go on, take the first tiny step. Even if it's messy. Especially if it's messy. Because really, what's the best that could happen?

Speaker A: Sam.

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