Rebecca Watson - Tech Sales and Relationship Building (#34)


Rebecca Weeks Watson is a digital media and tech entrepreneur who has been awarded two U.S. patents. After starting her career in finance and then consulting for, she decided to pursue her interest in the startup world. She was on the founding team and led Business Development (early tech sales) for two different marketing technology companies, one of which was acquired by Meredith Corporation. During that time she led the product development, launch, and distribution of social media products that became adopted by publishers and brands with a total of 200 million users worldwide.

She has spoken at 50 conferences nationwide and founded a groundbreaking interview series called The Reveal that uncovers the personal stories of world-class leaders. Currently, she enjoys teaching a Lean Startup class at Davidson College and lecturing at UVA’s undergraduate school of business.

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Episode Summary

“Too often I think people in the startup world feel like they have to know all the answers. They have to build these perfect shiny bright products to then reveal to the world. And at that point, it’s too late.”

—Rebeca Watson

In this episode we’ll cover:

  1. What is relationship building and why it is key in any venture
  2. Why Rebecca often reads headlines on LinkedIn instead of books
  3. How technical do you have to be to do tech sales?
  4. What is pre-selling? And why it is essential for startups to build a product that users crave.

Key Milestones


Grant Ingersoll (00:19):

Hello everyone and welcome to the Develomentor podcast, your source for interviews and content on careers and technology. I’m your host Grant Ingersoll. Thank you so much for joining us each and every week as we explore the different roles that go into building great technology, we have two simple goals. We want to showcase the interesting people in tech across a variety of roles and highlight the different paths they took to get to where they are. We hope you are listeners, just my find that little nugget of insight that helps you build the career and life you want. My next guest started her career in investment banking after completing a degree in finance before wading into the world of digital media. Along the way, she’s led a variety of teams focused on technical business development, picked up a few patents as well as held consulting and advising roles across a variety of startups. Most recently she’s the founder and producer of the reveal, a digital media company focused on showcasing how business leaders have used difficult life challenges to build a better company and life. As if that isn’t enough, she also finds time to teach at Davidson college. Please welcome to the show, Rebecca Weeks Watson. Rebecca, great to have you here.

Rebecca Watson (01:34):

Thank you grant. I’m so excited to be part of this.

Grant Ingersoll (01:37):

Yeah. And thanks so much for joining me. I know we’re all busy and, and you know, one of the things that I would love for you to just start off with is share a little bit more insight into some of that intro I just gave, you know, walk us through your, your career to date.

Rebecca Watson (01:53):

Sure. So I started at the undergrad business school at the university of Virginia and quickly fell in love with finance and the commerce track. I decided in my senior year to kind of follow the liquid of path. And many recruiters from wall street were down at our school recruiting early on in the year. And I felt like, gosh, you know, this high-level investment banking analyst position was sort of the most coveted. That’s probably what I should do. And not really knowing what my password was going to be or what my career trajectory would be. So I took that job and went out to San Francisco and quickly met with amazing startup founders and operators. And we were tasked with trying to fundraise for private companies in software, hardware and media. And it had a great experience meeting those executives and creative minds.

Rebecca Watson (02:57):

But what I really didn’t like was how much analysis and how much I felt like a robot some days and putting together those pitch books and it became very mundane and I realized this really wasn’t harnessing my strengths. And so I decided I’m going to go down and do something different. This was after the internet dotcom bust and I went to LA and said, gosh, I’m going to mix things up. I know that I love business development. I can see that I love relationship building and also strategy. And so one of the companies that hired me was sort of a middleman between media organizations and advertisers. And so I was meeting incredible minds and visionaries and the digital media and advertising space, and I was producing summits for them. And so trying to figure out what are some of the topics that they need help with is producing conferences, bringing in thought leaders, amazing authors in the space.

Rebecca Watson (03:57):

No, it’s an incredible opportunity to meet people who were leading these industries and also to sort of deepen my knowledge of those industries as well. And I started to see there are a lot of people that I’m meeting that are striking at big. So many of my, my clients are seekers or partners were, you know, acquired for hundreds of millions of dollars. And I thought this looks like a lot of fun. Obviously, you know, the sex appeal kind of draws you in. And so I started to put feelers out among my network that I wanted to get in on the operating side. And sure enough, I decided to join a cofounding team that was focused on digital media for women. And we were building software that helped sort of the top female bloggers and also every day writers produce and distribute their content in a beautiful format.

Rebecca Watson (04:56):

And this was a great experience and role for me because I was passed with business development, sales, PR and product marketing. I really didn’t know much about [inaudible] product marketing. So the first time that I was meeting with engineers on a regular basis trying to find that product marketing fit and I I was pushed out of my comfort zone for sure. During that time, three and a half years, one of our investors of a juror capitalists came to and set, I can see the tremendous work you’re doing in business development sales, I’d like you to come over and join another founding team. And so I moved up to San Francisco to join a team that was building software, also marketing software. But it was just simply an idea. And so I was the first person to have to go out and pre-sale the software and actually find out kind of what features we wanted to build.

Rebecca Watson (05:54):

So yet again, another learning curve, but all along way kind of loving this risk-taking and customer research and early selling. And for four years I did that. We built the company from pre product up to 90 million in revenue in four years. So it was a great, great track and I met some amazing people and colleagues were incredible. They’re about 120 of us worldwide and I started to have kids and I wanted a better lifestyle, not traveling as much, not having so many long hours and so decided to start consulting for various startups. And that enabled me to have my heat, lot of different projects, which I liked without having to do sort of the, the nitty gritty of the execution. And one of the startups that I was [inaudible] advising was conference and content producer for chief marketing officers. And what I realized in producing these events, I would ask many of the attendees afterwards what they enjoyed most about the summits.

Rebecca Watson (07:01):

Who did you like on stage? What were some of the content topics? You know, what, what really stood out to you? And in many cases, yes. Can you say, I really liked when my so and so role model on stage went off script and showed a vulnerable part of themselves or revealed something about a failure in your career or I had no idea this person had this also going on in their life cause I do too. And so the great point of connectivity and inspiration and authenticity for these people. And I’m first scratching my head after hearing this for like a year, a year and a half. Well these are the stories that people most connect with. Why don’t we have more of them in our media system? So I just said to just go out and start my own video interview series because I thought that video would bring that sort of sight, sound and motion to show emotion versus just write articles about these stories.

Rebecca Watson (07:57):

And so I founded the reveal and really just started cold calling executives, CEOs, business leaders. There’s to say that I wanted to share their stories and, and behind the scenes stories that they’ve never shared before and instantly on social media, these videos were so well received. I had thousands of views and replays and shares over time. And it’s been not only a hit for the end user to see as well as this speaker to sort of show there vulnerable, authentic side, but so just an amazing life inspiration for me. I’ve learned more from these interviews that I have for many self-help and business books and you know, I’ve read dozens and dozens over the years. And so I feel really grateful that this small little realization to turn it into a company has provided me with sort of all around benefit. And that’s where I am today.

Grant Ingersoll (09:06):

Wow. That’s so many things in there. And I think we probably could talk for hours on some of these things. In many ways. I think there’s an interesting piece here as you talk about how with the reveal, you know, these leaders seeing these insights into what many of us see as executives, often the high office and showing some of that vulnerability. I want to tie that actually back to, I think one of your early moves in that, you know, one of the things I love to highlight on this show is that, you know, you don’t have to spend your career doing the thing you went to college to get a degree in, right? You started off with this finance degree, you kind of took the traditional path. There was, you know, you admittedly say, you know, Hey, I was, I saw the salaries of these investment bankers and, and it kind of was this natural fit and then you know, you took a right turn, right? Or a left turn, however you want to look at it. If you could drill in on that a little bit more. Cause I think a lot of our audience, a lot of what I’m going after is really geared around helping people realize that’s okay. And part of that realization is like, Hey, other people have done it. Here’s how they’ve done it. So, you know, Rebecca, if you could share a little bit more as to what it, what, what went into that for you.

Rebecca Watson (10:23):

Okay. Yes, definitely. And, you know, it was a lonely experience as I’m sure a lot of people have felt. When you don’t feel like your strengths are being harnessed and you spend your time outside of work thinking of other things or what might be or what if, and [inaudible], you know, in those years working in finance, I was feeling [inaudible] failure actually, not because of what I was accomplishing or not accomplishing, but just that it just didn’t feel good. It didn’t feel right. And [inaudible] I applaud my parents for supporting me to go to seek out a career coach because I kind of get back to basics like, okay, am I good at and what am I interested in? And this career coaching company was great and that they did, you know, give you lots of assessments, whether it be skill-based function, you know, personality tests and whatnot.

Rebecca Watson (11:16):

And, and I learned some very eyeopening things that I, I really prioritize relationship building, love networking, you know, in many of the questions, my answer is centered around embracing change and being okay with risk taking. And and I also just loved the, the stories from the startups that I was working with. And so I realized that would be okay for me. If I would try to dip my toe into that and give myself permission to leave, what I thought would have been, you know, the best job in the world. The story that you, you told yourself that just reframing sort of what I thought that I should do and to something that I really wanted to do and pursue.

Grant Ingersoll (12:01):

Yeah. That’s great. I mean, and it’s actually interesting, right? Cause like, you know, on the one hand you’re highlighting, there’s this side of you that likes risk taking and then yet, you know, in, in that narrative that you just shared, there’s also this, Hey, I was outside my comfort zone. So even as a risk taker, there’s often still this tension with being outside over your ski tips as they like to say. And, and you know, talk a little bit more about that, especially like in, as you’re in these co-founder roles and you’re effectively pre-selling AKA, you know, it’s, it’s vaporware at this point. Like you’re out in front having to tell a story that doesn’t fully exist yet. Like how did you wrap your head around that and how did you make that work for you in terms of your own development, in terms of your career path?

Rebecca Watson (12:49):

Right in the beginning it was so painful. I distinctly remember one of the best stories I have about feeling uncomfortable and pre-selling [inaudible] was we, we’re selling software and tools to at the beginning gaming companies and at the time the biggest whale are largest organization that we wanted to sell to was Zynga. And Zynga was, you know, touching know 400 million users through their games on Facebook. So when I started this co-founding company and the, the [inaudible] initial visionary, the CEO said, okay, Rebecca, on your second day on the job, we’re going to go meet with Zynga. And I thought to myself, like, what?

Rebecca Watson (13:33):

We don’t have a product, we hardly have a name and a logo. And I’ve only spent a couple of weeks like between saying yes to the job and the first day on the job researching our competitive set. How we’re going to be different. Like I don’t understand this at all. This is just awful. And my husband is like, Oh my God, what did we agree to? And I remember sweating all morning walking into this meeting. But one of [inaudible] yes, it was the most uncomfortable I’ve ever been. But okay. Also simultaneously the best learning experience I’ve ever had that’s shaped my career because I realized, okay and similar to what we learned sort of in the lean startup approach is you never want to spend time building something you think or assume is going to be a great fit. Mmm. It’s best to use the beginning stages and your time and your energy to really understand what your customer wants in the end. What kind of need or problem are you solving? And so we went in there and really just listened. And that whole time that they were talking and telling me about the things their wishlist. I’m literally writing down our feature set to take back to the developers.

Rebecca Watson (14:50):

So it, you know, the fascinating learning experience for me. Like, Hey, I didn’t have to have the live product for them. All I needed to show was a commitment that we were wanting to be on their team to solve their problem. And so of course you spent the next two months and the sprint building the features that they wanted. And of course it didn’t end perfectly, but it was one of those days that I will look back on and say there is, you know, there’s a great reason to be sweating. It impacted how we went. And you know, too often I think people in the startup world feel like they have to know all the answers. They have to build these perfect shiny bright products to then reveal to the world. And at that point it’s too late. And so you know, we, the media, I think paint this rosy, glossy, beautiful picture of, of what those products look like, but really it’s all discomfort. It’s all mass and chaos. But do you enjoy that process and the, and the journey while you have it?

Grant Ingersoll (15:51):

Yeah. Well enjoy my be a strong word there, but like on the good days you enjoy it and there’s plenty of hard days in there as well. I love that though because I think you know, in many ways this is the entrepreneurial spirit, which is you’re creating the future, you’re creating your own future and you’re doing it by listening to the learning and being, you know, actively curious. Another interesting thing that emerged in your, as you’re describing your narrative and I think one that is at the heart of a lot of what I’m trying to get at here is helping people know and understand and develop relationships. And sometimes it’s a dirty word and that it’s, you know, it’s networking in the worst sense of the word, but at the end of the day, like the thing that has led to a lot of these opportunities for you is this relationship building. And so maybe, you know, drill in a little bit more on how you approach building relationships. If there’s particular mentors here you want to give shout outs to. I love hearing those stories, but you know, talk to me a little bit more about how you approach relationship building and how other people might learn from your approach.

Rebecca Watson (16:59):

Sure. Yeah. Relationship building is key no matter what industry or function you’re in. Your colleagues, how you treat them, them, you know, the respect that you show them, the activities you do outside of the office with them, they end up becoming some of your closest friends. Same with their clients. Do you know, I remember going to many sales meetings and partner meetings and realizing I’m just going to ask a lot of questions of this person, even side of what we’re supposed to be talking about or the product or the pitch and just get to know these people and get them talking and it relaxes them and you learn some things you have in common. And one of the earliest partner meetings I had when I was working with that woman’s business was a girl who is the exact opposite of mean and she was five foot one.

Rebecca Watson (17:49):

I mean, I’m six feet and she’s her parents from Pakistan and she has like dark black hair, dark skin and [inaudible], you know, from the south and blonde. And we couldn’t have been more different, but we just shared this passion for starting companies, which we’d love diversity. We loved going out and comedy and all sorts of stuff. So anyway, from that partner meeting we ended up becoming really close friends and I was just, I’m the matron of honor in her wedding two months ago. And so thinking about people as people, not just people as roles and realizing everybody’s fluid, these people are going to go on to maybe be investors in your business. They might go on to be you know, experts in a field that might be able to give you feedback. You just never know. And really to keep in touch with those people on it. You know, certainly LinkedIn has helped, but for sort of the online touch points that aren’t as meaningful. So I always encourage the students and they, the young executives that I’m mentor to really have one on one coffees and to ask people about their life outside of work because that’s how you forge those relationships and those end up being opportunities to your next venture.

Grant Ingersoll (19:01):

Yeah, that’s so true. I mean I think, you know, I always tell people it like what’s the worst that somebody’s going to say if you ask them is like, no, in many ways like this podcast I’m doing is simply my own selfish, Hey, I want to meet some people. And so I get to have a great guest like you on. So you’ve got this role in sales and business development and, and all of the, the best sales people I’ve seen in tech companies do this really fine line dance between understanding the technology, understanding how engineering works, understanding how marketing works, understanding how sales works and, and they, they can blend these things together. And, and obviously it’s built a, like you said, on these relationship skills, but in particular, you know, you mentioned, Hey, this is, you’re coming into the technology side of it. And more, how did you approach digging in and learning the technologies such that you could get to a level of where you felt comfortable talking about the tech side of it? Because that is always a part of technical sales. Right,

Rebecca Watson (20:06):

Right. Definitely. And that for me was probably the biggest difficulty I had at the beginning. It was, I was really intimidated by the development team and you know, I’m sure if I asked them, they’d say, Oh my gosh, I’m so intimidated by these extroverts of their developments, what are they going to ask of me? They’re going to want to go have a beer for five hours. So I decided I would just spend a lot of time with these people. And so we did not just like meetings, but I would go over there and hang out, try to listen to some of those words they were using, I knew I would never have a deep, deep understanding of the tech side and [inaudible], you know, clients, phone calls, they have important meetings that we would bring our head of development with me or sort of some of the engineers that have been working on a particular product so that they could get into the weeds. But what I really tried to do was to get as much info as I could without overwhelming myself because I wanted to take loads of information and whittle it down to the most important things to give my team and my sales people out in the field so that I wouldn’t on them either. You know, they needed sort of entry level understanding, but certainly not bogging them down because that’s also an opportunity cost too.

Grant Ingersoll (21:25):

Yeah, for sure. It’s one of the things I often tell my techies is, you know, like, Hey, there’s some real benefit for you to be able to communicate outwards in ways that don’t involve all of the low level jargon. Right? Like, think about how you would tell good friends who aren’t techies or you know, siblings or parents or, or whatever it is. I mean, I think you hit on some really key pieces there and in often and in this type of role as you, you need to know just enough, right? That’s one of the things that always amazes me in sales is like you have to be just enough of an expert to always be one step ahead of everyone. But you don’t have to be five steps ahead, right? Like, yeah. So

Rebecca Watson (22:08):

One of the hardest parts of that to being sort of in the middle there was the, the expectations and the timelines. That was always a tricky dance for me because you know, the clients saying, I need it, I need it, fix it. When can you have it? And I got to the point where if I was walking down the hall to get back to the team, they knew, but only, and first question was going to be, you know, is it ready? When is it going to be ready? And so I told, I told our head of development, why don’t going forward, you get me [inaudible] date [inaudible] actually 10 or 20% longer then when you think you would actually give it to me that way you don’t see me coming back and back and back and disappointed. Do you know what I mean? I was actually asking him to manage me so then we could give their pass that onto the client or the customer and they wouldn’t be disappointed either.

Grant Ingersoll (22:59):

Yeah, for sure. And yeah, it’s, well it even, I’m just sitting here like 10 to 20%. I’m like Oh yeah. But then we would probably blow past that too. So in your career description too, there was this yet another pivot here of you know, deciding you wanted to kind of step back from the step backs, not even the right phrase. Right. But like you wanted to change from this high pressure, you know, founding mindset and so you, you switched gears into advisory and consulting and you know, I think anytime we have these inflection points in our career, we go through quite a bit of process. I know I just went through that myself. But I’m curious like what nuggets now that you’re into your career a little bit further, you’re making yet another major life decision. What can you share that you’ve learned out of that part of your career?

Rebecca Watson (23:53):

Yeah, I think what I love about consulting and advising is the wisdom and I’m bringing from my career experiences to all the things. Not only that I feel like learned in launching or scaling, but but also the things that I did wrong that I can help teaching guide other startups to do or not do. And you know, we always, used to complain like when we would outsource to consultants or to other advisors, their hourly fee is so expensive. But then you realize when you’re one of those people, you’re doing a ton of research upfront before you actually are doing the calls or the meetings and you’ve use your career experience and you’re going to whittle it down to the most important things that you’re going to instruct or guide those companies to do. And so I’ve kind of loved that opportunity to get the most information that I can in a short amount of time.

Rebecca Watson (24:50):

The hard part is that I do like to execute. And so in some ways being an advisor is not as fulfilling to me because I like the scrappiness of actually getting it done. And so I find myself wanting to follow up with my clients, you know, months later and be like, I didn’t see this part of the site redesigned or you know, your SEO is still not, it’s still going to crate or whatever. It’s like, come on guys, like, let’s implement the changes that, you know, we discussed, but that’s up to the team to do. And you kind of have to learn to let go a little bit and leave a loose relation. It certainly doesn’t keep me up.

Grant Ingersoll (25:30):

As long as they paid their bill. Right.

Rebecca Watson (25:32):

Yeah. Right.

Rebecca Watson (25:34):

Yeah, no, that’s, I, I struggled with that and consulting as well. And I think it’s something that people going into consulting don’t always recognize. You know, I’d be remissed Rebecca, I think if I, if I did my homework right, one of the, and you didn’t mention this in your intro, but as I understand it, you, you’ve actually collected a few patents along the way. Is that right?

Rebecca Watson (25:53):

Yes, yes. And it kinda goes back to an amazing mentor that I met kind of randomly through again through relationship building person is this person is this person and I needed a marketing consultant. His name was Ed Tuck and he’s not well known because he’s recently deceased and it was much older. He lived into his nineties, but he was the founder of global positioning system. So GPS. And she has, yes, exactly. His company was called Magellan really early too, understand that whole space. And he, it’s always been almost a decade ahead of science and technology. But at the time he was putting together a team to scientific matchmaking and I had consulted for and knew a lot about the online dating space. And so he asked me to join his early team [inaudible] and we were putting together our heads around how can people use science and their DNA to avoid people that won’t be good matches for them, and what will the universe of people who would potentially be good, lifelong kind of partners for them.

Rebecca Watson (27:11):

And so I had the most incredible experience learning from him. I mean, every day we met, it was just pinching myself. I can’t believe I’m with the founder of GPS, but I remember early on he said, most of what we’re going to do is not going to work. Yeah. He was very candid and being like, Hey,uyou know, you’re gonna fail, you’re gonna fail a lot. But one of these things is gonna do really well. And uand so he was always kind of humble in that regard. But we filed multiple patents for scientific matchmaking. So there is the [inaudible] a bunch of paper out. Mmm. That were not really well understood. But we did, I’ll get into the science and we found that the more opposite your DNA makeup, the more likely you are to stay married to your partner. And in a lot of it comes down to the chemistry and the complimentary alleles.

Rebecca Watson (28:07):

It’s just like why you wouldn’t marry your cousin, right? Your DNA is too similar and it could lead to miscarriages and whatnot. And so this was phenomenal science and interesting to both eharmony and to match and all these other online companies. But we were super early on. And so if you think about it right now, this is kind of thing, the track that say 23 and me and ancestry and Ancestry and other companies are doing, which is [inaudible], you know, spit in a cup and look up your DNA. [inaudible] What can you learn from that? How can you improve someone’s life? And so we were trying to improve their relationships, but in that role with this company, you know, there’s a why I invited up and how much is involved in filing a patent. The timing it takes to even get it approved, you know, all the details. Do you have to describe and graphics and writing and just, Mmm, totally impressed by all the people out there who’ve gone that track because it is so rigorous and it’s expensive too.

Grant Ingersoll (29:09):

Yeah. Well, and that’s, that’s perfect cause I mean, I think one of my questions is like, you know, kind of what has been the impact for that. Obviously it’s a little hard to measure like, Oh, Hey, I hired you specifically cause you have a patent. But I mean, I imagine, you know, some of the things you you’ve described there have have helped you going forward in terms of establishing credibility in terms of, you know, yeah, I’ve been there, done that and, and Hey, I know what it’s like to be a founder and things like that.

Rebecca Watson (29:39):

Right, right. And I think it’s [inaudible] to me it felt like making a case in extreme detail and also improving your differentiation. So every time you’re thinking, okay, well someone that the patent office is going to ask, well it’s still not quite as different as on to competing product or I still don’t understand how these two things are linked or what exactly this function does uniquely. And so you’re constantly diving deeper and deeper and into you know, how it’s used and to how it’s made up. And so I think it, it helps you understand the value of those details and then also seeking out other people on our team, whether it be, you know, the other technical person, the attorney on our team, you know, we had a, a matchmaking science professor on our team. And so to constantly be, be working together and to collaborating to come up with those answers was a great value to me. And I’ve benefited from [inaudible] but listening and working with them along the way.

Grant Ingersoll (30:44):

Yeah. What a great experience. I mean, I, I know in my own career, early on, like just being, I, I worked for this really tiny company, but we did a lot of different things and just that exposure to so many different roles. I often reflect back on what a difference that’s made. Obviously I don’t have any way of testing against it, but it helped me tremendously in my own career and it’s something I encourage everybody to dig in on. And maybe that’s a good segue into kind of where you’re at now. And as I understand it, you’ve taken and are laid some of this advising and consulting and now you’re actually advising students, you’re bringing it back into being an instructor. You’ve got the reveal going as well, but you’re also teaching you know, how is [inaudible]

Rebecca Watson (31:29):

And that’s how that happened was really interesting. Yeah. You know, how, like when you look at that and your top, but what does the angle with the students? Well, you know, all right, thank you. They had the business school, like I said, all these wall street and accounting firms come to recruit you. And so I kept in touch as an alumni. I wanted to mentor students who wanted to come out to Silicon Valley and weren’t that many of us. I mean it tends to be a lot of Stanford and Berkeley and the, you know, the same old people find a job. And so I was really eager to have more East coast students and people that I could help come out the West coast and get involved in the startup scene. And so I just offered to my undergrad business school, Hey, no one at the school ever showed me what was possible and a startup or entrepreneurship track.

Rebecca Watson (32:21):

Can I come back and talk about innovation? Kind of talk about what life is like at a startup. Can I talk about the various roles in a startup? And so I started to do this annually and sure enough, we create an entrepreneurship minor and it’s been a huge hit. [inaudible] That sort of led me, now that I’m on the living on the East coast now, we moved to Charlotte, North Carolina to be closer to my family. Mmm. You know, Davidson college that, Hey, can you come teach a startup class to these students? Because you know, a lot of them have been coming out, going into medicine and into law and to finance, but they need to sorta see what’s possible and tech and innovation. And I love that creative thinking because it doesn’t need to be something formal. It doesn’t need to be something oversalt. But just showcasing anecdotes of executives just like you’re doing grant with this podcast, you know, showing people here’s different routes, here’s different paths and they’re not all going to look the same. But to give them permission to try I think is really key.

Grant Ingersoll (33:25):

Oh yeah. Wow, that’s great. And I can’t even think back in 2007 when I started my company and went out and, you know, we raised money in the Valley and all that kind of stuff and like, I was just clueless. You know, and, I was in an area at the time, I mean, I was in RTP, Raleigh Durham research triangle park. And you know, there’s, there was some startups at the time, but it was mostly just big corporate, you know, tech companies and like just no clue. And so the thought that something like that existed then that would’ve been really helpful. So it’s great that you’re, you’re able to create that in a place that, that doesn’t have it. So I can imagine that’s very satisfying in terms of the giving back aspect. You know, you, I think we all reach [inaudible]. Yeah,

Rebecca Watson (34:11):

It really is. You know, the unique, yeah, about the most recent course I taught was a combination of students and local executives. And you know, there was a head of Corp strategy for a fortune 1000 business there. I mean he has a startup in mind but doesn’t know, you know, the first steps to take. You know, there’s a 70 year old gentleman there who said, I keep retiring but I’m failing at retiring. Any startup ideas, you know, everybody can leverage their creativity and their dreams. They just need a little nudge and they just need a framework to kind of put together what those first steps are. So in that regard, I love being able to sort of give that nudge and give that pep talk and and to help them take those first steps.

Grant Ingersoll (34:57):

Yeah. And who knows, maybe someday they’ll be your guests on the reveal as well.

Rebecca Watson (35:03):

That’s right. Yeah. Maybe they’ll give me some, some stock.

Grant Ingersoll (35:09):

[Inaudible] That would be fantastic. I want to kind of take this to a couple of final questions here, Rebecca, and be conscientious of your time because there’s so many great things in here. We probably could keep talking for hours, you know, as, as you take and reflect back and especially now that you’re in this teaching position and yeah. What’s your advice to somebody getting started who maybe wants to get into content production or, or wants to, you know, get into, you know, advising startups or participating in startups. What are some of those key nuggets you, you wish you knew back then?

Rebecca Watson (35:48):

Sure. I think it is much more important to look at a particular team or a founder or the industry that a company is in to see that align sort of with your interests. And with, you know, your values and somebody you think has a great track record or at least seems that they’ve, they have or they will have what it takes to make a successful company. I think those things are more important than the specific function or title that people take, especially in those entry level positions. I mean, you think about how different roles will change over the years and when you’re in a startup, if you can just get your foot in the door, you’re going to be exposed to so many different committments and you’re going to be involved in collaborating with lots of different types of people, different types of roles and functions that pretty soon you’ll find out what’s going to be the right fit for you.

Rebecca Watson (36:47):

And you know, one of them, the best interviewees that I’ve had the chance to have on my show, this gentleman named John Chambers said, listen, we’re at this stage and sort of the technology and career and that, you know, people are going to change every three years. And if you’re not, if you’re not either getting permitted or a new different type of department or moving on to a different company every three to four years, you’re going to get left behind. And so I think the, the permission to kind of try something new that you don’t know a ton about or you don’t know where it might take you, I think is okay. In fact, I think it sounds like from what he’s described, it could be an asset.

Grant Ingersoll (37:29):

Yeah, definitely. I, I love to you know, I like this notion of guided exploration and I think that’s one of the things that underpins a lot of what, how you’ve described your career is this notion that, Hey, you know, I’m, I’m kind of on this road, but if there’s something interesting over here and like, I’m going to go try that out. And that’s led to so many serendipitous moments and opportunities for you.

Rebecca Watson (37:52):

That’s a great point. Right? You might as well try.

Grant Ingersoll (37:54):

Yeah, exactly. And you know, what do you have to lose? Right? Especially in the tech space anyways. Now that may change, but you know, for the time being that’s, that’s the world. I’m wondering if you might highlight for our listeners a couple of resources, maybe a book or a podcast or another website that has been particularly helpful for you in terms of helping you figure out these things. You mentioned the career counseling or coaching early on. Any other resources that come to mind?

Rebecca Watson (38:23):

Number one, I think where I spend the majority of my time consuming information and trying to understand just school in general is LinkedIn. So the stronger and wider your played, you know, the better the content that you’re finding there. But I love seeing what kind of partnerships people are announcing, you know, what kind of companies getting funded. I find that I have a much more diverse set of points to LinkedIn because of the my network versus if I only, you know, read certain types of books that I intended to read or that I highlighted or particular sites that I’m going to bookmark. Right? I’m always going to be sort of hearing the same type as authors or writers. And so I kinda liked that about LinkedIn is sometimes you’ll be like, Oh, this isn’t really relevant, but I’m kind of reading those headlines. Hmm. That’s interesting to know. And I think it makes me kind of more than culturally aware, which definitely helps in a business sense about where kind of trends are going, how roles are changing, what people are thinking about. And it’s a great resource for me.

Grant Ingersoll (39:33):

That’s fantastic. It is funny because I think I remember when the LinkedIn feed came out at first I was like, huh, why, what, why? Why is this a thing Arthur, all these other news feeds and then, but then I think you hit the nail on the head that it’s a professional filter and that can be really helpful.

Rebecca Watson (39:52):

Yes. And I think, you know, it combined sort of the, the more formal announcements with also people’s kind of ramblings and thoughts, which is unique because you can, you can understand what, you know, these connections that you have are thinking that you might not have learned about them just in regular conversation. So that’s also neat from a relationship building standpoint too.

Grant Ingersoll (40:14):

So true. You know, Rebecca, this has been awesome having you on and there’s so many things in this that I think our listeners would benefit from. Perhaps learning more from where can they go to find out more about you, maybe follow you on Twitter what’s, what’s the best way to connect with you and learn more from what you’re doing?

Rebecca Watson (40:34):

Yeah, definitely. Definitely Rebecca Weeks Watson on LinkedIn is probably where I post the most of my ramblings and occasionally some articles and content. And then the videos on the reveal and if anyone wants to email me, I’m [email protected] and we’ll continue to produce those videos and hopefully inspire business and people in life. And and then I’m on Twitter as the reveal co.

Grant Ingersoll (41:04):

That’s awesome. Rebecca, thanks so much. We’ll be sure to link those up in the show notes. Yeah, no, definitely. And for our listeners, as always, if you’d like to show, we’d love for you to subscribe to our podcasts on either iTunes or whatever podcast app you’re using these days. You, of course, can also visit us at to hear older episodes as well as find other content on careers in tech. Most importantly, if you like the show, please tell your friends. Referrals are the lifeblood of any podcast, and if you have any feedback, please feel free to reach out. Or perhaps you even want to be a guest or you know, somebody who could be would be a great guest. You can drop us an email at [email protected] otherwise, we thank you once again for listening and we hope you’ll be back next Monday for the next episode of develomentor

Additional Resources

Selected Links from the episode:

Rebecca’s interview series, The Reveal
[email protected]