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From Engineering to Entrepreneurship: Defining Your Vision, Seeking Feedback and Ensuring Scalability - Jen Sargent, CEO Wondery (Amazon Podcasts)


EPISODE SUMMARY


Are you looking for a playbook on how to pivot from engineering to entrepreneurship?

Jen Sargent (CEO of Wondery -Amazon Podcasts) shares her remarkable journey from being an electrical engineer to running a successful media company. With her diverse career background and expertise in male-dominated industries, Jen provides invaluable insights and advice for entrepreneurs, women in male-dominated spaces, and those interested in managing teams.


Jen Sargent is the Chief Operating Officer of Wondery, the largest independent podcast publisher in the world.  She is a successful entrepreneur and executive with 20 years of digital media experience.   Prior to Wondery, Jen was as the CEO and co-founder of HitFix which was acquired by  Uproxx. Her previous roles include head of Online Marketing & Development for Reed Business Information (parent of Variety); venture capital experience from BV Capital in Hamburg, Germany; and finance experience from JP Morgan investment banking in New York. Jen earned an MBA from Harvard Business School and a BS degree in Electrical Engineering from the University of Virginia.




PODCAST OVERVIEW


1️⃣ Pitching and refining your idea for success

2️⃣ The power of adaptation and pivoting

3️⃣ Navigating male-dominated industries and rooms

4️⃣ Importance of diverse mentorship and sponsorship

5️⃣ Overcoming challenges and taking the entrepreneurial leap

6️⃣ Valuation, funding, and owning your ideas

7️⃣ Building a solid team and finding product-market fit

8️⃣ Negotiation skills and the art of making successful deals



PODCAST DETAILED TRANSCRIPT

Sirisha Kuchimanchi:

Hello, everyone. This is Sirisha, and I host the Women Career and Life podcast. I am excited to have Jen Sargent. Jen is the CEO of Wandery which is right now part of Amazon podcast and Jen and I met through the Podcast Academy. We both are on the board and we were running for election and we are so excited to be part of that community as well. Jen's had a very diverse career. Actually she's one of the few people who I've seen. So she originally is an electrical engineer by training but now she runs this huge media company and we are going to find out about her journey, her entrepreneurial journey itself, some of the lessons she's learned. So some of you who are either looking at entrepreneurship in the future or in that pathway right now, or maybe the only women in the room thinking of what the next steps are, or even talking of venturing out, managing teams, so many aspects, I would say tune into this conversation to listen to what she has to share with us today. Jen, thank you for being here, I've been looking forward to this chat.


Jen Sargent:

Sirisha, thank you for having me.


Sirisha Kuchimanchi:

Yeah, absolutely. So as I mentioned, you're an electrical engineer by training but how did you end up in media? Because looks like a large part of your career has actually been in the media industry.


Jen Sargent:

Yeah so I studied electrical engineering as my undergrad and got a degree in it but my very first job out of college was in finance at Morgan on Wall Street. And what I found out of college is that an engineering degree is a fantastic background to do a lot of different things. And in fact, when I was considering what to major in, I was deciding between business and engineering. And a college professor had recommended to me that if I wasn't sure, start with engineering, because I could always pivot from there. But if I started with business, it might be difficult to go into something so much more technical. And it worked out great for me. I think part of what makes engineering special is the fact that you learn how to solve problems. And most businesses require problem solving. So if you get that skill down from the beginning, it translates to a lot of different things. But my first job out of college was in finance. And then I think what really struck me was that I won't say jealous, but I was finding myself advising companies who were operating in media, in tech and entertainment and making recommendations, but not being able to see the recommendation through as an operator. So after that experience at Morgan, I thought, how do I get closer to the operating side where I can actually get my hands dirty and start doing these things? And I was always a fan of entertainment, I was always a fan of media. And with my engineering background, I was drawn to companies that were data and tech focused. So that really helped point me in that direction of getting into the media space. So my next job after Morgan was really getting more into media and advertising, and each subsequent job after that got me a little bit closer to my personal passions as well as this intersection of entertainment and technology.


Sirisha Kuchimanchi:

I'm so glad you started with a plug for women in Stem because those who are at the crossroads trying to figure out engineering or business I think you said it well. And your professor was right, because I have. A lot of conversations as a tech person when people are talking about business and engineering and if they're not sure it's the same recommendation. Because from engineering you can pivot anywhere else. But if you sometimes have other majors, transition back is a little bit more challenging to come back and figure out what you want to do. So I think your story speaks to that in a lot of ways.


Jen Sargent:

Yeah, I mean, I'll just add to that too. Podcasting didn't exist when I was in college, and a lot of the careers that women are going to go into in ten or 20 years don't exist yet. So you want to give yourself that optionality. And when you're not 100% sure, and most of us are never 100% sure about what they want to do in the future, just this idea of always learning, always being curious and giving yourself options really lets you flex when the right thing does come along.


Sirisha Kuchimanchi:

Very true. And even if you know what you're going to do, I think you just said it right, ten to 20 years, it's going to look different. So it doesn't matter what you think you're going to do now, because there's going to be different opportunities come two decades from now. So you said you transitioned to media, but along the way you started your own media company way before you came to wander. So what made you decide to do a startup and how did you decide what to focus on? Because I think that's one of the challenges for entrepreneurs, right? Either you have a ton of ideas or a dirt of ideas sometimes when you're trying to figure out so what made you decide to take that leap of faith and how was that transition?


Jen Sargent:

So it was a mix of things. I was always someone coming up with a lot of ideas and I think it was a little bit of ego at the time as well, where I would come up with ideas and the places I was working. It just felt like I thought I could execute the idea better or I could do my boss's job, or that I had a bigger vision than some of the people I worked for and I would chalk that all up to ego and fearlessness as a younger person. But it was mostly about ideas and just loving to build new things. I always was scanning and looking for that thing that I could go do. And it wasn't until I was gosh in my early thirty s that I really landed on something that I thought spoke to my skill set. And also a personal passion of mine. And where I thought there was a gap in the market in terms of actually getting a business off the ground. That was a lot of work. And it was also a big mental shift to say, okay, am I going to leave my good paying job, that's stable where I know what I'm dealing with and go out into the unknown? It was very scary. And I worked on my idea for about a year just behind the scenes at night and on weekends to really flesh out all the details because I wanted to be as sure as I could be that this was the right thing to go after before I just quit my job. And what also made it a little tricky for me was the timing. So I started my first company in the fall of 2008 and that was a very tricky time. It was an economic downturn. It's now been labeled the Great Recession. But while I was in the process of fundraising and really bringing everything together for the business, the market had collapsed, Lehman Brothers went bankrupt. There were all these different externalities that happened that really put a kink in my plan and I thought, gosh, is this just the wrong time to start a company and should I still do this? And my husband at the time was very encouraging and he said, look, you're employed now, you'll be employable in the future. If you want to go do this, do it. There's never going to be a perfect time. And I think there's a lot of things in life that there's never a perfect time where you're never going to get the stars to align. So you just have to take the leap of faith. And so that's what I did in fall of 2008.


Sirisha Kuchimanchi:

First of all, when you talked about the ego statement and doing your boss's job. I was just like internally smiling in my head because such a true statement, I think oftentimes we may feel that. And I'm glad you kind of pushed forward, right, because after getting a ton of experience, if you're driven, you're curious, you like to learn, you'll pick up those skills and then you realize that you can do a lot of other people's jobs. And to be able to push forward and say, I am going to do that, I'm going to challenge that either by pushing yourself in that corporate chain or stepping out like you did, sort of courageously and saying, I'll try something else because I'm in that phase right now. I just quit my corporate job a few months ago. So I'm in this transition phase, trying to figure out what that looks like with some ideas and trying to, how do I say get more clarity on this, trying to decide between those three things, like you said, gap in the market, what is my skill set and what is my passion. And it's kind of a hard thing because today this seems like the thing, tomorrow that seems like the thing and just trying to narrow it all down and figure it out.


Jen Sargent:

I'm smiling as you say this because as you're talking, I remember that time, I remember that feeling and it's both exhilarating and terrifying and you just need to persist through it to really keep challenging yourself to focus and find the right next step because it is a huge transition.


Sirisha Kuchimanchi:

It is, absolutely. And I think the other thing is, as you said, this is what I kept telling myself and when someone asked me, I say the same thing is your skill set doesn't go away. So say you try this journey and you decide it's not for you or you want to go back, that you can always go back to your old job or some version of it, because you obviously leave a good trail behind. That you can always get called back. Or you can find another venture that combines your new skill set with something you learned before. Because I've gone through layoffs and being a stay at home mom and haven't always been able to transition back to work. And that's what kind of in my own head I'm thinking, okay, there's always a sort of backdoor exit to figure this out, but I'm not planning to use that exit. But there is always that option there if needed.


Jen Sargent:

I realize now with perspective too. At the time I was worried about that same thing, like, oh, if I go do this, will I be employable again? And what I found is employers are not going to ding you for taking a calculated risk. In fact, they're going to applaud you and it's going to show your willingness to take risks, your willingness to stretch. I didn't realize that at the time, but now looking back when I have to explain these career moments. I found them embraced with open arms and not a negative at all.


Sirisha Kuchimanchi:

Yeah. And over the time I started podcasting when I was working and it's taught me so many things along the way. Not just the technical parts, talking to people, just expanding my network, meeting different people. There's all these little things that you pick up along the way that when I have conversations with my colleagues who I used to work with, it's an interesting conversation because there are aspects that they haven't seen either. So there are skills that you'll take back. Right. I think more about you willing to try something new is something I would say incredibly commendable for someone to go and try something different because it is hard to make that transition and change that mindset and have a support system around you while you're doing that and find that support system wherever you can. It be family, friends, externally, wherever it is. Right.


Jen Sargent:

Figure out you bring up a really good point because startups inherently are not stable. And if you're looking for stability from your job, startups are not the right path. Having that stability come externally, like you said, from friends, from family, from another source is really important as entrepreneurs go down their journey.


Sirisha Kuchimanchi:

Yeah. And to have someone to bounce your ideas and play devil's advocate because in your mind, this is the perfect thing. I mean, why would someone not want it, but someone else to kind of understand the perspective. So what are some things how did you narrow down your idea? I know you said you looked at the three aspects, but how did you decide what to focus on and what were some of your first steps and some of the mistakes that you made along the way?


Jen Sargent:

Gosh, I made a lot of mistakes. We probably don't have enough time on this podcast. In terms of how I narrowed it down, I had ideas along the way and I never felt like they materialized into something real. The business that I started in 2008 was called Hit Fix and it was an entertainment news brand focused on helping consumers discover and experience movies, music, TV. It was, in essence, a consumer version of Variety, or kind of like Entertainment Weekly is today. It was breaking news about things that consumer fans of entertainment care about. And I had an idea while I was working at Variety, where I was working closely with that team, and we saw a gap in the market for consumers. We saw consumers coming to Variety, which for those of you not familiar with it, is kind of the bible of the entertainment industry. It is a B to B trade rag that essentially covers the inside baseball of entertainment. And we saw consumers coming to the site looking for that scoop about things that they cared about, but then getting turned off when they would read about the agents and the hiring and firing and how much this person got paid on a deal because that's not really what they cared about. They wanted to know when their favorite movie star was going to be in the next installment of their favorite film. And so we saw that gap. We did a lot of research and ultimately I was trying to get Variety to do this deal. And when it went all the way up the flagpole to the owners of Variety, they you know, we love this idea, but we are planning to sell Variety. We're going to divest our whole U. S. Division and we don't want to change the business model right now. And I said, OK, could I get permission to get a carve out from my contract to continue to work on this idea? Because I'm really passionate about it. I've seen the data, I've seen the gap and I want to keep pursuing it if I can get permission. And that was one of the key lessons I learned in business school, is always own your ideas, especially if you're employed when you're coming up with them, you want to make sure that your company that's employing you doesn't actually own your ideas. And that's a very tricky balance. So I tried to be really transparent about it, get that permission before I pursued it. And I did get that permission. And they said, you know what? We do not care about this. You can go off and do it. Don't use your company computer, and good luck. So I had that opportunity to get real market data before I was able to jump off and do it. If I hadn't had that opportunity, I would have tried to validate my idea in other ways, but this was just a very ripe in the market way to get some assurance that I was at least on the right path.


Sirisha Kuchimanchi:

Yeah, that's good. I guess you were up enough to realize that you needed to get the permission from the company and own your idea beforehand, right? Because you're so absolutely right. It's a tricky balance. I mean, as simple as this for my podcast, though, it had nothing to do with my company. Even before I launched it, I got permission from my legal team, my HR team read all the conflict of interest because I just didn't want it to become something that could potentially be a barrier if I wanted to grow in my organization. So I didn't create any challenges before that. And same thing no using the computer, no using office time, which is all fine. I kept track of everything. Everything was at home, separated, so someone thinking about it. I think it's good to keep those because it's not about just taking the time for the idea itself, but you don't want to burn those bridges by souring any relationships. I think also when you're going forward with this, even if you choose to exit your company, as you go forward, just keeping that in mind as well. So now that you had it all wetted out, you started your business. Did you have a co founder? How did you proceed with it? How did you find customers or clients or start your magazine or was it an online issue?


Jen Sargent:

Mostly it was an online website, almost like a series of blogs that came together. So I did have a business partner. I worked with him at Variety on this project. So we were really 50 50 from the beginning in terms of concepting this idea and seeing the gap in the market. And I really don't remember which one of us approached the other of like, hey, should we just still go do this even though the project is canceled? But somehow, very quickly we connected and we were both super passionate about it, so decided to pursue it. I found having a co founder and business partner tremendously helpful. Being an entrepreneur is so isolating. You're on an island, you have 1000 things to do. Like you mentioned before, you need someone to be able to play devil's advocate and really bounce ideas off of. And I found that having a business partner also kept me personally accountable where we said we were going to do something by a certain date. And I felt accountable to him and he felt accountable to me. And it made us push our business forward even when we hit tough times or points of uncertainty. So that was a big one in terms of actually starting to get our customers. We had this idea of bringing in tastemakers from different verticals. So we started having those conversations early, trying to convince people who also had good paying jobs and staple jobs to leave those jobs and come start writing for us. And we were able to find a hybrid where we could start working with people we wanted to work with and not fully employ them, where they would consult for us, they would do blog contributions and they would be able to dip their toe in before they left their jobs. But it was a series of those conversations. And one of the things I realized as an entrepreneur is you have to be comfortable selling. And by selling, I mean pitching your ideas, whether it's to VC investors or whether it's employees or partners. You're always trying to convince people. I felt like I was pitching my husband sometimes because I was trying to convince him that I should go do this and not take a salary for a year or two while I pursued it. But you're constantly kind of pitching and in that pitching process, you're refining your idea. People are poking holes into it and you start to see whether there's a there there if you're successful, convincing people to join you or whether you have to keep looking. So it was a lot of that. Once we had our base team in place, then we built the website, but we started breaking stories and those stories helped us build our initial audience. So we started small. I remember the first day when we got probably 1000 people to the website and then each subsequent week grew and some weeks we fell backwards and some weeks we grew and we had to look at the data and try to figure out, okay, who is our customer? Is this starting to click? I remember early on doing a lot of customer research and validating, okay, what parts of this website and content are resonating, what's not resonating? Who is our target customer? Do we need to refine it? And trying to find that product market fit. And that is a hard thing for a lot of businesses to do because until you have a product market fit and in our case it was entertainment fans coming to read this content, then you don't really know if there's a there there. So that definitely took us some time.


Sirisha Kuchimanchi:

Yes, I think the theory of the idea and the practical execution and the actual selling of it is completely different. Right. So when you were saying you were doing the selling and how did you generate revenue? Was it through VC? I mean, then you did startup costs because you were getting all these bloggers to show up to write for you. You get it through VC, did you run it through ads? And how did you generate the first thousand customers? Did you have a social media platform that you were building? Buzz, what would be that strategy you used for ours?


Jen Sargent:

We did both. So I started with Angel Investment and I went to people that I worked with previously and I gave them the pitch and I said, hey, you've worked with me, you know me, would you like to invest in this opportunity? And I explained the business and it really took a lot of courage for me to muster up just the energy to ask people I knew for money. That was probably the hardest thing for me to get comfortable with. And as soon as I did and I got my first yes, I realized, oh wait, this is not as hard as I thought. And people who know me or who are friends of people who know me are the strongest people to go to because they know my work ethic and they've seen me in action. And once I got over that barrier of being afraid to ask people for money, we raised about a million dollars in Angel Investment, so that definitely helped us get things off the ground. But then we immediately pivoted into our business model, which was largely advertising, so it was getting movie studios and TV networks and companies adjacent to the entertainment space who wanted to reach consumer entertainment, fans spending to reach those customers through mostly digital ads, email, and then eventually video ads as well.


Sirisha Kuchimanchi:

And your experience, I guess your prior experience gave you an idea of what price points to put for all of this? Because that's the other part, right? For someone starting new who's not familiar, I think it's hard to decide what your leverage is and what to negotiate and how much you should charge for something, right? And from everything I've read and seen, people tend to undersell, sometimes significantly so, because you're not confident, comfortable, you're not sure how to pitch. So you're at that point, the debate comes to, should I take whatever I can get or do I hold off and push for what I should get?


Jen Sargent:

I'd encourage entrepreneurs to get as much advice as possible and get as many comparables as possible. So in our case for advertising, how much we should charge, that was not a hard exercise because we could talk to people we knew and get rate cards from comparable companies and find out this company charged a $30 CPM, and this one charged a 25 and this one. And so getting to the actual price points there was pretty easy. What was harder was around the angel investors and our valuation and how much we should be kind of, quote unquote, selling the company shares for, because that is very subjective. And it's partly the merit of the idea, it's partly the entrepreneurs behind it, but it's also the confidence that the entrepreneur exudes and the excitement they can build around the particular idea. And it's hard to put a number around that. So a lot of times those things have to come together with some luck and some market timing, and it's like, okay, is my idea worth a million dollars? $10 million? $100,000? I have no idea. But inherently, if you're going to take people's money, you're backing into some sort of valuation. So that was the trickiest part. I talked to a ton of different entrepreneurs and I got a wide range of opinions, and then I just had to apply my best judgment. And to this day, I couldn't tell you if we got the right price for that first round of funding, but we got the funding and if we hadn't gotten the funding, we wouldn't have proceeded. So it's a little bit of a balance there. But I'd say that's where I just encourage entrepreneurs just get as much advice as possible.


Sirisha Kuchimanchi:

Yeah, I think most of us are visual of it is really Shark Tank, right? That's the closest we come to seeing something like that, because most things happen behind closed doors and we have no.


Jen Sargent:

Visibility to it 100%. And these things aren't public. A lot of times, these early rounds of investment in terms of what the valuation really was at the time, whereas certain things, like the price point for consumer products, for advertising, that's readily available information that you should be able to track down.


Sirisha Kuchimanchi:

So now you're growing, you have a plan, you're executing on it. Did you always have an exit path because I know you sold your business. So did you always have an exit path for acquisition? Or what were you thinking your potential growth plan was? And how did that come about? Did they approach you? Were you looking for people? And how did you walk that path?


Jen Sargent:

As soon as we took in Angelvc investment, having an exit plan became more important because I think most of those types of investors really look to have a return after seven years or ten years. And so we really had to critically think about it at that point. Now, having a plan and having a path are totally different. Our plan was to get acquired, but you can't just wake up and say, we're going to get acquired and have that magically happen. So I know what we did to create our path, but looking back on it, I would have definitely done some things differently. And I think the things I would have done differently would be to not overly focus on an exit and instead first focus on just building a viable business that can be standalone and that can flourish regardless of who owns it. And if you do that, it will become something that's attractive to many potential acquirers. But the second thing I would have done is really had a work back and said, okay, who are the potential acquirers? We did that part. It's this company, it's that company. Here are our ten potential acquirers. Well, to get someone to acquire you, it's like a marriage and you need to usually date them first. And so you need to think about how could I start to be in business with this company that could acquire me through some sort of commercial arrangement in a way that they can get excited about my business without having them learn every single little nitty gritty detail about my business, but really have that dating period. And that's what I would have done more intentionally and deliberately if I had known then what I know now. And in the places where we did create those commercial relationships, we had a true conversation about acquisition. In the places where we did not create those, even though the company was a likely acquirer, they were like, well, we don't know you. We get pitched every day. And it wasn't something that really ended up materializing. So having that work back plan of potential acquirers is important to just think about who you're building relationships with and if there's no possible commercial path, still being very thoughtful about building relationships with the operators at that business, that was another thing that I didn't realize. How many decisions are really made by the operators, not the M A teams, not the bankers of whatever company it is. You need someone who's an operator who's really putting their name against an acquisition and sticking their neck out to acquire the company, because acquisitions don't work out a lot of the time. So just. Like marriage at 50% of marriages don't work out either because it's hard. It's really a difficult thing to bring two cultures together. So that's something that's worth thinking about.


Sirisha Kuchimanchi:

Upfront and when you say operator, what do you mean? Because I'm not sure everyone understands what that means.


Jen Sargent:

I mean someone who's actually owning A-P-L within the business. So the people who are making the day to day business decisions and accountable for the budgets for whatever division you might be aligned with. So for example, we ended up getting acquired by a smaller company, so that was a little easier to navigate. But for example, if you were hoping to get acquired by an entertainment company like Sony, well, that's a very big company. Is it the movie division, theatrical division, is it the television division? Know which part of the company and which division specifically would be interested in this acquisition? Who actually runs that division and is in charge of the P L? That's where you need to kind of understand the decision making because otherwise you approach these big companies and you don't get to the right person.


Sirisha Kuchimanchi:

That makes total sense because you only see the headlines in the end where it shows the C suite execs and the acquisition. But you're saying that's not the people who are actually finally deciding on the deal. They may be the ones who sign off on it at the last minute, but there's a lot of steps in between that work through as you go through this transition.


Jen Sargent:

And even I'll use a more recent example, Wondery getting acquired by Amazon. We had two commercial relationships in place with parts of Amazon way before we even thought about acquisition. We had been licensing our content to Audible and we had been working with them on a few projects. And then we had started a commercial relationship with Amazon Music, which also has podcasts on the service. So we had two different parts of Amazon that we had some experience working with before any kind of acquisition conversation even started to come up.


Sirisha Kuchimanchi:

And I suspect that when you're having these acquisition conversations with one company or many companies at the same time, there's a lot of things going on. So from your standpoint, how did you learn those negotiation skills? I'm sure you learned them as you were going to. Like you said, sales was one of the biggest things that you needed to as a startup that everyone needs to think about. So how did you navigate that? And if you have sort of competing offers, there's probably culture piece. How does the structure look after you're acquired? Not just a dollar figure, right though? That's the one that we all look at when we see it, but there are so many other pieces about sort of their mindset because very often it's your child, your idea that you are selling. So there's a lot of emotional attachment to it as well. I would suspect. So how did you navigate that? How did you acquire those skills, that thought process? And who helped you sort of buffet and think about this, work through this process, like, walk you through some of this because there's a lot of learning along the way.


Jen Sargent:

Yes, gosh, those are a lot of questions. Let me start with how I negotiated it or approached negotiating it. In my personal time, I actually read a lot of negotiation books because I knew that that was something that was going to be important every step along the way. And in fact, it was. If I was negotiating with a potential employee about their salary, if I was negotiating with an advertiser who was going to be a client of ours, and certainly in the acquisition process, there's a lot of negotiation. So part of it for me was trying to equip myself with some of the basics of negotiating, but then part of it is really learning on the fly. I'd say the biggest part of negotiating, though, is working backwards from what you want. And so many people don't take the time to first think about what outcome they want, what is their desired outcome, what would be a price for this company or for this salary or for whatever it is you're negotiating? What would be acceptable? What would be a very positive outcome for you and really going through that exercise and understanding it before you try to launch into a negotiation? Because I find people sometimes come to the table without that crystallized in their mind, and then they do things to undermine themselves in the negotiation because they're figuring it out while they're negotiating. That would be just my general life advice for entrepreneurs, is like, figure out what you want first and then go ask for it. In terms of the actual specifics of negotiating, I recommend having a banker or someone to be the middle person when you're doing something high stakes, like an M A transaction. Because when your company is getting acquired, you're essentially negotiating with your future boss. And so if it gets ugly, if you need to ask some hard questions, sometimes a third party can ask for those things on your behalf in a way that you can still maintain the relationship between you and your future boss. So that was something that I didn't fully value or I undervalued the first time I sold a company. So my first company, HitFix, got acquired by a company named Uprox, and we did not have a banker do the negotiation. I did that negotiation myself. And that is where I learned, wait, it might be better to have a banker or a broker in between for wondery getting acquired by Amazon, we most definitely had a banker, and that really helped. Just keep the process smooth and have that buffer.


Sirisha Kuchimanchi:

Yeah, I mean, everything you're saying is so invaluable for someone thinking about it. But even the negotiation matters even in a corporate job, first time salary, when you're getting hired, when you are hiring someone, it's not just for entrepreneurs, but to think of what the outcome is. Right. Even a potential conversation that you're trying to partner with someone with the money on the table or without money on the table, because there are so many non sort of economic standpoints that can be negotiated out when you're thinking of different aspects of it.


Jen Sargent:

Yeah, but you asked before about the other aspects of it. And I will go back to my marriage analogy, which is it's more than just the price that gets paid. It's also what this relationship is going to look like for you as a founder. What is your role going to be? What is your path? Are you set up for success? How will your success be measured? Will you have autonomy and decision making? Is your team coming along with you? What is the intent of the acquisition and kind of working out those things? Because when you have a plan and you've communicated ahead of a deal, going through it makes everything so much smoother than if you're just focused on, okay, I'm getting this payout, and then I don't care, because you do care. Because, like you said, it's your baby. And this is something you've built. So taking the time to work out all of those details, and that's one where I recommend talking to other entrepreneurs who have sold their companies and they can tell you what things they did right, what things they did wrong, what things to look out for.


Sirisha Kuchimanchi:

Yeah, and you said it differently also right. The negotiation is not figuring out on the fly. You have to know what you're looking for because as an exit path, it's not just the economics. It's a blending of two companies, two personalities, and understanding that the personalities are going to work well together. Because otherwise it's just going to be I mean, you hear of acquisitions that have gone really terribly badly, right, either immediately or three years down the road, they spent billions, and it was just a sort of disastrous merging. So the products didn't work, or not just personalities, product mix, or what they thought was the market wasn't really the market, or it was just a way to think of the competition and get ahead. There's so many ways this thing can also not go well. And how do you figure that out as you're thinking about it?


Jen Sargent:

I think there's a tendency as a first time entrepreneur to think, okay, I'm going into an acquisition discussion, and the acquirer is asking all the questions, and the entrepreneur is doing all the answering. But it really should be 50 50, where you, the entrepreneur, should be evaluating the acquirer just as critically as they're looking at you. So asking those questions, looking under the covers to understand, okay, what is the financial position of the acquirer? Are they really equipped to take on my company. What is their plan? Is it a good plan? Is it a plan I want to be part of and really asking some of those probing questions to the extent that you can. So you are going in just eyes wide open to what the situation is.


Sirisha Kuchimanchi:

I so totally see so many parallels to corporate life, right. Even when you're interviewing for a job, you always think the power lies to the employer. But no, it rests as much with you because you want to find that what they work on is important to you, their culture is good, you have the right opportunities. And also you kind of lose your leverage at that point because that's the only time you have real leverage. It's an entry point after that. You might have little bit here and there, but not really ever as much as that first entry point.


Jen Sargent:

That's 100% correct.


Sirisha Kuchimanchi:

Yeah. So I'm assuming a lot of these conversations, oftentimes you were probably the only women in the room. So if that was the case, is that something that struck you as different? And if it did, what did you do to be heard more or to get what you wanted out of the discussions? Whether it be internal to your company when you're setting up the company, it could be with your employees, could be in very many conversations.


Jen Sargent:

Yeah, I can share my approach. I'm not going to claim that it's the right approach, but it has worked for me. I have mostly been in male dominated industries and male dominated rooms ever since I was an electrical engineer in the lab building a microprocessor or in the boardroom and everything in between. And I do try to turn on my EQ as much as I can in terms of understanding the differences between how men and women communicate, how men and women make points, how things I could do would be helpful or distracting. And it's not to say I lose myself, but I also realize that, for example, men sometimes talk over each other or they will interrupt each other, and women will wait a minute to jump into the conversation and then never have that opening to make their very good point. And realizing that I took a different approach. I do take a different approach when I'm in a room full of men versus a room full of women and making sure that I can get my voice heard in the room or things like that, that you start to notice and pick up on. Then I try to make the change in my own behavior to adapt to the room I'm in, and that's been helpful. And then also as a woman, I'm always encouraged to get female mentors and female contacts, and I really appreciate that. But at the same time, working with so many men, I realize that I need sponsorship from men as much as I need sponsorship from women. So really building those relationships with both the men and the women in the orgs that I'm in has just been tremendously helpful. And I've been very lucky to get sponsorship from men in the organizations. And that really helps pull women up. So other women can pull women up, but men being sponsors of women, so just being aware of that and building those bridges and relationships, I think is really important.


Sirisha Kuchimanchi:

Yes. And if you're looking at the tech sector, I mean, it is heavily male dominated. Right. You need men as sponsors, no matter which sector you're in. Oftentimes you need men as sponsors and something to think about because you might have women as mentors or sponsors, but you need both of them. And I like what you talked about interrupting because very often in the podcast, even here, when we're having a conversation, I'm not jumping in to interrupt you. Well, one part is for the editing part for me, but secondly, it's not something that comes naturally to jump in and stop in the middle. We tell that the men and other women should make sure that they amplify the voices. But I think you've kind of also given a sort of twist to the script, which I really like is don't feel hesitant about interrupting because it's something that doesn't come naturally to us. We wait and we stop and we think about it. We think it's impolite, but if you need to be heard, the conversation is too far along, you can't go back three steps. I think it's so critical. I really like that it's something that maybe I'll even do it in the podcast just so that I can make sure I catch you at the right intersection. So as we're talking, what are the three sort of tips you would give for entrepreneurs or women entrepreneurs that they should do, like first three steps? When you're thinking about this, we talked about a lot of things. So what would be the three steps?


Jen Sargent:

The three steps for basically getting started?


Sirisha Kuchimanchi:

Yes.


Jen Sargent:

I would say first, clearly defining your idea and pitching it a few times to people, you know, hearing yourself say it out loud and letting them poke some holes in it and really making sure that you've landed on something that you believe in. One thing that I don't think I did enough of is going from my idea to the future version of my idea and saying, does this thing really scale? Does this scale? How will I scale? And I think I could have shopped my idea along to other people more upfront to get that feedback, to really force myself to think about, okay, this is a good little idea. Is this a good big idea? But really just crystallizing that idea and talking about it and shopping it. Sometimes entrepreneurs get nervous about sharing their idea because they don't want someone to steal their idea. And what I've learned is that ideas are a dime a dozen, in a sense, because the hard part is the execution. The hard part is quitting your day job and putting all your energy into something like this to grow it and nurture it. And not many people have the willingness to do that. So yes, be careful who you share your idea with if they're a direct competitor who is well positioned to steal the idea. But outside of that, most people don't have the stomach to steal your idea. So really do try to crystallize it up front. The second thing is finding an accountability partner. If you're not going to have a co founder or a business partner or someone who's really working alongside you, find an accountability partner. Because like I said, it's so isolating, it's so hard to build something from nothing and kind of be on your own island. And so if you can create that kind of accountability partner in some aspect of your life to really just keep things in check and moving forward so many people I know who have great ideas get stuck in this phase of, I have my idea. I don't know how to get it off the ground. And they can't get that momentum to get it to step two and three. I think having accountability, external accountability, can be really good for that. The third thing I would say, and I'm trying to think, is this the third thing or maybe there's probably five more things, is don't be afraid to pivot. Don't be afraid to pivot your idea to evolve and change it. Sometimes you get locked into the original thesis and what you wanted to do and you've said it to so many people that it seems scary to change it or to say that you're wrong, but really be willing to take a data and customer driven approach. And when you get information that's contrary to what your thesis is about, your idea, really scrutinize it and be willing to make changes as soon as you get that information. Because when I look back at some of the missteps in my career, especially in my entrepreneurial career, it was missing key moments like that where we could have made a pivot and we didn't either dive deep enough into some data or customer feedback or we just didn't want to pivot, essentially. So those are three things I can spend a lot more time on, five more things. But I think those are a good start.


Sirisha Kuchimanchi:

Yeah, I mean, those are amazing because I can tell you from experience that that's exactly the process I am going through and trying to figure out. And it is quite hard trying to the accountability, the pivoting, the customer research and not sharing the idea, sort of this dichotomy of how much do I share? Can I pivot? After I've shared the idea, will it look like I wasn't committed to the first one? All of these already you are going through so much changes all this self doubt about is that the right thing or did I lose the passion? Am I being distincere to myself? And I thought that was the most problem I wanted to solve and it's not the problem I want to solve now and it's an evolution in progress. But I think the other part of it in conversations is sort of the sunk cost, right? Just because you sank time and money into something and you know that's not going to work, don't spend more time and money throwing at it, just abandon it and move forward with what is the right solution to go ahead with.


Jen Sargent:

That is great advice. And I think if you look at companies in whatever space you're in that have been successful, if you go back to where they started, I guarantee all of them have had a pivot along the way, or they discovered something that broke open their business model and really helped them scale. And it's different than what they contemplated when they started. And letting self doubt or these other things creep in, it's not productive, it's not going to be helpful. And to the extent you can just keep a lid on that so that you can continue learning and being willing to just challenge yourself, you'll get to a better outcome.


Sirisha Kuchimanchi:

Absolutely. I mean think of even Amazon. It started with selling books and it's launching Shuttles on space and that's how I look at it and doing podcasts and selling fruit and vegetables. I mean I know that's not its only product portfolio but from the other stuff we think about, that's what it's doing and airbnb from where it started to. I mean all these companies are a completely different evolution of where they started from. So don't look at page 100 of the book, look at page one or page zero when they were looking at it. So absolutely. So as you're getting ready to wrap up, this is a question I ask every guest what advice would you give your 21 year old self?


Jen Sargent:

I would tell my 21 year old self to trust her gut. I think especially in my twenty s. And then in my early thirty s I was keenly aware of the fact that I didn't have that much life experience and that the people I was in the room with, whether they were investors or business people, partners, et cetera, oftentimes they were 10, 20, 30 years older than me. And I always valued the fact that they had more experience than me. And there were two occasions I can think of where I truly deferred to someone with more experience, even though my gut instinct and feeling was something different. And in the end it ended up being a bad decision both times. And the sooner someone can realize, finally hone and trust their gut instinct as an entrepreneur the better. Because you're the one with the drive, you're the one with the get up and go, you're the one that created this idea, and so you need to be able to hone and refine and rely on your own gut instinct. And I think I finally got there by my mid to late 30s, but it took a little bit of time.


Sirisha Kuchimanchi:

That's such great advice. What is the one word you'd use to describe yourself?


Jen Sargent:

It empathetic.


Sirisha Kuchimanchi:

I think from what you said earlier, it helped you connect even as a leader or as the one person, like you said very often when you were the one women in the room with the men, I don't think it was necessarily empathy as much as figuring out how to read the room. Right. That's how I see Empathy. Empathy is not about just hearing someone not feeling great about themselves and connecting, but able to read the room as well and connect with them as people or their ideas or where they are sitting at different levels.


Jen Sargent:

I think whether it's negotiating an agreement or attracting the best talent or working with and maintaining client relationships, trust is a big part of those relationships. And for me, leveraging empathy to build trust is part of how I approach relationships. So I think it's helped me in a number of those areas.


Sirisha Kuchimanchi:

Yeah. Jen, we've run out of time. I just wish we had another hour. There's so much to talk about. And this has been great because it's not only that you've shared lessons on your journey, what worked, what didn't work. As I'm going through some of it, I can see so many parallels with it. And for those who might be even working in a corporate structure or a sort of a more different structure, not an entrepreneur, I see so many parallels with that as well. Negotiating, speaking up in the room, so many aspects of it that do actually even speak to those conversations. Because every one of us runs a business, whether we run an actual business ourselves or our careers are in microcosms of business, right? Because we are trying to grow, we are trying to scale, we are trying to either make more money, get more benefits, expand networks, everything, so it all speaks similarly. And just being able to articulate, speak up, gather inputs, find sponsors, all of that becomes very important in this conversation.


Jen Sargent:

Well, thank you. This was so much fun chatting with you, and I want to wish you good luck on your journey as you're figuring this all out.


Sirisha Kuchimanchi:

Absolutely. Thank you so much.


Guest:

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Wondery : Website


Host: Sirisha

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