How Real-World Experience Helps Founders Spot Market Gaps

Intro 00:01
Welcome to Startup Success, the podcast for startup founders and investors. Here you’ll find stories of success from others in the trenches as they work to scale some of the fastest-growing startups in the world. Stories that will help you in your own journey. Startup success starts now.

Kate Adams 00:18
Welcome to Startup Success. In this episode, I sit down with Cortney Woodruff, co-founder and CEO of Assemble. We discuss how Assemble is working to expand access to industry-led education, and what Cortney has learned from sitting on both sides of the venture capital table, he shares how founders can stand out beyond traditional networks and pedigrees, and his advice for building with conviction when investors don’t immediately see the opportunity. Welcome, Cortney. So, Cortney, thank you so much for being here.

Cortney Woodruff 01:04
Thanks for having me. I really appreciate the opportunity to chat with you.

Kate Adams 01:07
Yeah, I mean, you have such a cool background. I mean, looking at it, you’ve built companies and raised capital, and you’re now an angel investor, and you’re leading Assemble. We want to get into Assemble and all your experiences, but it would be great if you could give us an overview of your background and what led you to where you are right now. I think the listeners would find that interesting.

Cortney Woodruff 01:33
Yeah, I think along that list of accolades, which I’m grateful to hear you say, is more important than any of it is. I’ve learned a lot of lessons.

Kate Adams 01:42
Yeah, I bet firsthand. You’ve learned lessons firsthand.

Cortney Woodruff 01:47
A lot of firsthand lessons. So a lot of band-aids. A lot of patchwork over here. But Cortney, who am I? So I’m originally from Jackson, Mississippi, and growing up, I’ve just always had an affinity for business and soccer, sports. Yeah, it just grew up very, very amazing. You know, family and community. My grandparents were entrepreneurs. My dad, you know, has stories with my aunts of growing up in one of the first black-owned grocery stores in the city.

Kate Adams 02:22
Wow, cool.

Cortney Woodruff 02:23
And so it just I think I kind of have always had that entrepreneurial spirit. I remember in third grade realizing that when I went with my mom to Michaels, as she would buy supplies for like cross stitching and things, I didn’t realize it, but I had free working capital, so I would get heard about me all these arts and crafts, and go and customize necklaces and bracelets for my classmates, and and come back home every day with you know 25 to 40 bucks worth of worth of orders, so.

Kate Adams 02:55
Wow, it’s in your genes. The entrepreneur drive is in your genes.

Cortney Woodruff 02:59
Yes, so naturally that progressed. I attended Alabama A& M in Huntsville, Alabama, which is an amazing HBCU, and I graduated with a degree in economics. And from there, I took maybe eight months off after graduation, and just being a little ambitious, decided that I would go over to Europe and try to explore what it was like to be in a top MBA program. And some kind of way, it was a five-day trial. On the third day, they kind of pulled me out and aside and said, “Hey, would you like to interview for our full-time program? And I was like, “Okay, when? They were like, “In the morning. I was like, “Okay, this is interesting. Twenty one, with the eight-hour notice to interview. But nevertheless, I did the interview on a Thursday and on a Friday, I had a welcome packet to the graduating class of 2013. And I thought initially, okay, that means I need to go work for two years, and you’ll reserve my place. And they said, “No, school starts in 10 days, so you need to go back to the states, and you need to be back here in Spain within the next nine days. (Wow!) And so that’s kind of always been the trajectory of my life, dreaming about things for 4-5 years, and then boom, God just puts me in these places. And from there, that was a really great experience. But I actually, which we’ll get into, I went into business school with the idea that I would either do investment banking or I would start a startup. I mean, I had this idea called Trainers Vault at the time, and I was very serious with the admissions office as I pitched it and said, “I’m going to start this company. I’m from America. You can see what happens when young innovators, you know, decide to build these software companies from scratch. And either it’s going to be that, or I’ll be like the other 380 in the class, and I will figure out how to go get a job at Barclays or Goldman Sachs or J.P. Morgan or maybe even consulting. So I did the first year and I realized that tech was really in my heart, and I ultimately moved to where you are. I lived in a hostel in San Francisco. And I lived in a hostel for maybe six months in the city, Alamo Square. We incorporated the company, 1052 Fulton Street. I’ll never forget it. And we built that company. And ultimately, I lived in the garage in San Jose for another year. And once the company was ready, and I felt confident that I had gotten an MBA in the hard knocks of being an early stage entrepreneur from Mississippi that had never been to California, I ultimately took the mega bus down to LA, and the rest is kind of history. So that’s kind of how I got my beginning.

Kate Adams 05:49
Wow!

Cortney Woodruff 05:50
I guess genesis into the world of startups.

Kate Adams 05:53
Yes, what a story! I mean, you – it’s like these opportunities came to you, but you were ready. You went for them without a lot of preparation. You really just dove right in.

Cortney Woodruff 06:04
Yeah, and I, I think you know, as dramatic as it sounds, I went from Mississippi to Spain. I booked a one-way from Spain to San Francisco. I would take the mega bus from San Francisco to Los Angeles to build a network, and I guess like one of the key learning points of that is yeah opportunities come to you, but sometimes you have to be very drastic in going to them and creating the luck.

Kate Adams 06:32
And it sounds like you were, you know, you had a lot of just kind of you know your background, your drive, your ambition. It sets you up well when you dove right in. I like it.

Cortney Woodruff 06:44
Yeah, you know, I’ve always had this metaphor in my head because things are really hard. You want to get into the best MBA program in the world. You have no network. You’re from Mississippi. You go to a relatively small school, so that’s not my world, right? I’ve always taken the analogy. You think about a column of bricks, or you’re bricking, or you’re building a house, and you’re laying bricks on top of it. You might just have to lay each brick individually, and it looks amazing once the house is finished. But that first day, there’s just mortar and slabs of brick and concrete everywhere, right?

Kate Adams 07:20
Right.

Cortney Woodruff 07:21
And so you just sometimes have to realize that you’re gonna have a lot of calluses on your hand. You’re gonna have a lot of blisters. It’s gonna be very sunny. You’re gonna have to build each scaffold for each level of floor of that building, but ultimately it may become a beauty when that entire thing is bricked and you can see the outlines of the cement and the mortar in between them.

Kate Adams 07:40
Yeah, wow.

Cortney Woodruff 07:41
If that’s what it takes. That’s what it takes.

Kate Adams 07:42
Yeah. Yeah. Good point. That’s a great way of framing it. I like that. So okay, that’s quite a background. Tell us what you’re doing now. Tell us about Assemble because it’s a really great concept.

Cortney Woodruff 07:58
Yeah. You know, I think thinking about my journey, even going from a relatively small school as a HBCU and trying to build a tech company out of my dorm, but also wanting to experiment with Wall Street, there were just moments where I felt that the the resources just weren’t there to to make the dreams that I had a little bit more optimized or efficient, and how I processed and navigated those worlds. And I mean that was you know decades ago. And as I fast forward, you realize that that is honestly a pressing challenge for 85% of universities around the world. There you know is this standardization of education, right? And you have all of these various laws and regulations, but at the end of the day, it feels like somehow we got lost in like what is the purpose of college, and it is to really be a bridge between high school and early stage employment.

Kate Adams 08:59
Yeah.

Cortney Woodruff 09:00
And so what we’re doing at Assemble is, we’re not only serving as that bridge, but I think we are building the infrastructure, the future of college, to kind of get back to the basics of how does industry connect with all universities, not just the Ivy Leagues or the ones that are in large metropolitan areas, and then also how do we allow universities to communicate with industry and bring those leaders into the classrooms as well? So, long story short, we work with the best and world sought out professionals inside of organizations, and we are designing curriculum and then using software to automate all of the governance and documentation that is needed for universities to really stay within the the realms of the law. And then using software to really help them optimize how they work inside of the universities to get these courses conceptualized, approved, and distributed to their students.

Kate Adams 09:58
Wow, it sounds like you’re making education much more relevant, right?

Cortney Woodruff 10:03
Yeah, relevancy and accessibility are like two of our key pillars, and I like to say, you know, I think one of the benefits of me being able to get into the top business school in the world eight months after being an undergrad and living in Mississippi was I could just see the contrast in a school that could, you know, you say, “Hey, I’m looking to try to get an internship on Wall Street. Is there anyone in the, you know, the business center or the finance department that’s worked at J.P. Morgan or Morgan Stanley? Because I was the kid that had Wall Street Journal delivered to my dorm, and I wore spooks to class, and they would go no good luck. So I went and created my own opportunity, but when I got to business school on any given day, there was Secret Service, and there may be the president of France there to speak to us. (Wow!) And so that’s a stark contrast. And if I had gone to business school, you know, eight to 10 years after being an undergrad, I may not have appreciated it as much, but because it was so soon, the contrast was just like night and day. And I think we’re really solving for that because it’s typically only the you know successful people because it helps with their brand, they will go pop up at Stanford, or they’ll pop up at MIT or Harvard. It looks good, and they probably have friends and colleagues that work inside of those organizations. But we’re building for the students that are in Doha, Qatar, Saudi, or Arkansas or Mississippi, like me, that are reading about household names that are in the Fortune 100 index, but they have no way of having access to anyone inside of those companies.

Kate Adams 11:46
Yeah, that’s so great that you’re doing this. Can you give us an example of like a piece of curriculum or who you’re working with?

Cortney Woodruff 11:56
Yeah, actually, I’ll give you one that hits a little close to home, so we’ll go back into the world of media and entertainment or arts. My business partner, Cortez Bryan, he’s my co-founder in this company. He built a long-standing career, which started his junior year in college. He was a junior at Jackson State, which is actually where I’m from, and he had a best friend that he had grown up with that called him by the name of Little Wayne, and he said, “Hey, you know, I’m on tour. I don’t really have anyone to manage me. You’ve been like my big brother, and you’re the only person I trust. You want to drop out and come manage me? And Cortez ultimately figured out how to do that, take a gap year, and he learned how to DJ, be the business manager, and he successfully managed Wayne’s career and watched him become one of the biggest artists in the world for 18 years. And in between that, there was this other guy from Canada that came down, and they signed him, and he said, “Hey, I think I want you to be my manager. And that artist’s name was Drake.

Kate Adams 13:04
Oh my gosh!

Cortney Woodruff 13:05
And so that’s happened over and over again. And so one of the first classes that we designed was a course, around careers in the music industry. And I don’t know if you know about the educational system of higher ed, and as it relates to music, but there’s not many music programs around. Obviously, USC has an amazing program now, thanks to Jimmy Iovine and Dr. Dre. Berkeley has one, and then under Clive Davis there’s a school in New York. Well, we designed a course, and it was a hit. I mean, I think within the first 30 days, 18,000 students just directly bought it and streamed it and had access and insights into how was this album rolled out with Drake or how did you navigate touring for Wayne and what are the underlying business models of everything. And we donated that course to Jackson State and what we found out was because we had taken the time with our process to design a college level relevant curriculum, he now could actually teach. And I think it hits on three of the pillars. A, students now have access to someone that, unless they were prepared to go spend $80,000 and go to the USC School of Jimmy Iovine and Dr. Dre School of Music, they would never have access to someone like that. But secondarily, the university wins because there’s a lot of press and fanfare of them being able to attract someone like that back and add something to their course catalog of that nature. And it drives enrollment, and it obviously with enrollment drives revenue and retention. And so for us, that’s been a really good case study, seeing the impact that that has had on the school, and realizing that okay, that was zero to one. So now, how do we do that 10x? You know, across all categories.

Kate Adams 14:56
That is such a cool example. Really powerful. I mean that shows exactly what you’re doing and how relevant it is. And like you said, it’s making it so much more accessible. How did you, how did you all come up with the idea for this? Like, what spurred this, Assemble?

Cortney Woodruff 15:14
The why. I would say, this is rooted in who we are as people.

Kate Adams 15:22
Okay.

Cortney Woodruff 15:23
I’ll tell you, you’re having Wall Street Journal delivered to you in a dorm room in Huntsville, Alabama. You’re inspired by Mark Zuckerberg and Facebook, and you realize that there’s no one within a 100 square mile radius of you, or 1000s for that matter, that have proximity to any of that, right? And so that’s kind of been something that I’ve always carried with me. And as I’ve mentored and gone back and spoken to college students, I can just see that that problem still exists. So in a way, building for me, and then the same with him. He just happened to become one of the biggest music managers in the world because his best friend of childhood became a global superstar while he was in college. And he always said there was no course of action. I had to learn everything the hard way, you know, and lessons can be quite expensive physically and financially and just mentally, right? And so, I think we both have always been trying to build what we were solving for. He was retiring out of music and getting ready to build a school. Had donated a lot of money to a university, and we put our heads together and said, “Like, what is the most impactful way to do this at scale. How do we get you back on these campuses to be the person that you wish you had, and how do we build something that I wish I had before I had to fly around the world just to find mentorship and advice? And I think the other thing is by us having access and true understanding of going to under-resourced institutions, we are attacking this thing from a different lens of just the education system is broken and we have resources and we want to fix it.

Kate Adams 17:13
Right, I see what you mean. You are your just your whole approach is so unique than anything we’ve seen.

Cortney Woodruff 17:21
Yeah, it’s unique, and I think we see you know gaps and arbitrage and market opportunities that just the average founder in the space or the typical founder in the space just doesn’t even know exists. To be honest with you, and that’s how we’ve been able to generate meaningful revenue for our partners as well as ourselves.

Kate Adams 17:42
That’s so great. It shows like you have that entrepreneur founder mindset. It really does. You’re solving this problem in such a different way.

Cortney Woodruff 17:53
Yeah, I think it goes back to first principles, right? So the average, you know, I remember talking to a really big, and and I don’t know, your audience might laugh at this or roll their eyes, or maybe they may even appreciate it. But I remember talking to a very big VC in this space, one of the largest. And I was able to get with the founding partner of the firm and explain what we were doing. And I mean, the case studies for us, you know, expand. We work with USC. We’ve had conversations and been at MIT, but for us, we thought that you know smaller schools, community colleges, and HBCUs could really benefit from this. And you know, I walk him through it, and he goes, “What’s an HBCU? And I thought, “My God, how do you run a portfolio that is, you know, $4 billion worth of assets in this space, and you don’t understand one of the most pivotal pillars of education in this country.

Kate Adams 18:51
Right?

Cortney Woodruff 18:52
And so when you do that, you realize that they have no idea what the campuses look like, what the culture is, and just the unique opportunities in general. And that’s just like a microcosm and one example of many where I think that we are just uniquely positioned in this space because a lot of people are coming from it with a master’s and a PhD of education from an Ivy League, and we’re coming from it with a master’s and PhD of getting out of these institutions and changing the world at the highest level.

Kate Adams 19:21
Right. You’re you’ve got the real world take on it, not the…

Cortney Woodruff 19:25
Yeah yeah bottoms up.

Kate Adams 19:27
Right. I love it. So I read you do some investing too. Do you think that helps you? Like because you kind of have the lens of an investor as well.

Cortney Woodruff 19:40
Yes and no.

Kate Adams 19:42
Okay.

Cortney Woodruff 19:43
Investing has, I think, for me because, in a way, as a minority, somewhat it felt isolating, right? And sometimes you’re trying to figure out what it is that you don’t know, and you’re just trying to, you know, find the bits and pieces of information to plug in the gaps. So I think investing has given me the confidence and the insights to be able to judge myself as a founder.

Kate Adams 20:12
Okay.

Cortney Woodruff 20:13
But it doesn’t really necessarily help me as an operator because just sitting on the sidelines and praying for someone to do their job is different than being the person that has to do the job.

Kate Adams 20:23
Right. Right.

Cortney Woodruff 20:24
And so it’s different, but I have made some early stage bets, and I’ve tried to keep them focused within the educational sector. So one of them is Subject.com, which is like the Netflix of high school learning. (Oh, cool.) Yeah, that’s a really exciting one. Obviously, it overlaps with what we do, as we design curriculum for higher ed. But I’m really excited watching that company. Michael Verlardo is the founder, and he’s an exceptional, just just an exceptional founder and entrepreneur himself. And I watched that company over the last six years grow from an office in Beverly Hills, and now one in Austin, Texas, and I mean, they are killing it in this space.

Kate Adams 21:05
That’s got to feel good as an investor, right?

Cortney Woodruff 21:08
Yeah, it does. And once again, even though it’s in my sector, you know, I check in, I’ll text them from time to time. But I think it feels good because I’m in the space, so you know, occasionally there’s just like unique insights. And I’m able to just like chat with him, and there’s no pressure coming from us, right? But it’s just more like, hey, here’s an opportunity, and oftentimes there’s a level of respect because I’m also in the space. As opposed to just putting in my two cents, literally, right, right, yeah. So yeah, but I enjoy it. I enjoy it. I think the biggest benefit for me, outside of you know, hopefully seeing the ROI, you know, within the next five to 10 years and some of the things, it’s just, just when you’re sometimes feeling like you are climbing up a wall and you can’t see the top of it. Occasionally, you want to just know you’re not going crazy. You know, you may see different companies getting funded, or you know different founders, and you’re just trying to figure out what the hell is going on. What am I missing something?

Kate Adams 22:14
Right.

Cortney Woodruff 22:15
What are the unspoken rules? What are the hidden gems? Right. What’s the playbook to this thing, right? So being able to be on the other side of it and see what other entrepreneurs are doing – that’s been beneficial.

Kate Adams 22:28
That makes a lot of sense. What have been some of the hardest things about being on the operating side?

Cortney Woodruff 22:34
Oh man, I mean, I think once again, there is – you know, unless you were an intern, you know, like so for example, one of our investors is Joe Lonsdale, founder Palantir in 8VC, right.

Kate Adams 22:49
Oh yeah.

Cortney Woodruff 22:50
And Joe loves to talk about his early days as a ace. So you have this ecosystem of being inside of Stanford, and then you have the ecosystem of being an early intern inside of PayPal. And you’re learning from Peter Thiel and Reid Hoffman, and all of these guys, right? So you can see how they’ve handled conflict, how they built teams, how they scaled teams, how they fought with each other and got over it. You know, I’m sure he saw Elon get kicked out of PayPal. So you see all of these things, and so you now have an MBA in running a company. Unless you’ve gone through Y Combinator, and that’s still like a little like low touch for every little intricate detail of your company. Just everything’s hard because you don’t have a playbook of knowing what to do or what not to do, right? So, have we screwed up fundraising before? Yes. Have we screwed up go-to-market? Yes. Have we screwed up technology? And I mean, every one of these things, as a founder, you just feel like your life is just ending if you don’t fix this within 30 seconds. And so, I’m sure that’s just like a lot of trauma stored in my body because it’s just like so brutal, brutally painful. I should probably go get that checked out. But you build a level of resistance and tolerance, and you know, thick skin is one thing, but I think as a founder in this space, there’s just a whole nother level to it. And I’ll give you a great example. It’s like when you first launch a product, you can just see it when you’re an early founder. You’re just so nervous, and you have that moment where you just want 100 people to come to the website, and then it crashes, right? And then you fix it, right? And then the second time you do it, you’re like, okay, there’s anxiety that we’re launching these things, but like the bugs don’t really bother you as much because you’re like, we will fix it, it will be okay, the world will keep continuing, and actually no one will really even remember it. Right?

Kate Adams 24:52
Right.

Cortney Woodruff 24:53
And then by the third time you do it, you have this anxiety of pushing something, but it’s just normal. And if you’re a really good founder, you’re actually having those moments quarterly or weekly as you’re pushing features over and over again. But you always remember like your first time, and just like the emotions and the nerves, right? So that’s just kind of like an example.

Kate Adams 25:14
That is a great description of being a founder. It’s like, yeah, you summed it up perfectly. It’s a good segue because we always wrap up the show. It’s the favorite question: What is your advice for other startup founders listening?

Cortney Woodruff 25:30
Ooh, that’s pretty broad.

Kate Adams 25:32
Anything like just you know, it’s run the gamut on the show. Some people say get a therapist. Some say work out all the time. Others, you know, say put a community around you. Like, what’s helped you?

Cortney Woodruff 25:46
I think okay. For some reason, my spirit is saying this: You have to be even in a world where AI and news and things are making it feel like companies are being born and generating profit and being sold every day. I think as a founder, you have to really be patient. Speed and execution helps.

Kate Adams 26:14
Okay.

Cortney Woodruff 26:15
But you have to be patient with yourself and the market because you can’t control the market. And if you really look at most successful companies, I mean, you know, Nvidia and and and SpaceX and Tesla, you know, these are like household names, and it and it just looks all of a sudden like Jensen Huang is a rock star, and this, you know, we have the first, the world’s first trillionaire, or you even go back down to like Brian, Nate, and Joe with Airbnb. The first two companies were started in the 90s.

Kate Adams 26:47
Yeah, good point.

Cortney Woodruff 26:48
And before these guys were able to get a check from Sequoia and get through YC, they were battling for three years. Now, obviously, the market may not always wait for you. Even with Assemble, we’ve had highs and we’ve had lows, and it’s been like eating glass for five years. But if you stick to it, you either pivot, or you join something, or you stay isolated and solo as a company. But you have unique insights on now how to handle the highs of the market, the lows of the market. You can see the opportunity. You can see what players are staying in the market and in the game, and which ones have died out, which probably weren’t as passionate about it in the first place. And so you gotta, you also, you know, speed to execution wins things, but you also have to remember the lesson of the tortoise and the hare.

Kate Adams 27:36
Yeah, point, good point. Yeah, I appreciate you being so candid on this show and really talking about the founder experience and like sharing your background the way you did. It was very helpful for listeners. Where can they go to learn more about Assemble and what you’re doing? It’s so cool.

Cortney Woodruff 27:55
Yeah, yeah, please, please. And if and by the way, we are getting ready to grow the team. So you are really passionate about education, higher ed. We are working domestically as well as internationally, and it doesn’t matter. We want passion and bright, smart people from the ages of 18 to 60.

Kate Adams 28:17
Awesome.

Cortney Woodruff 28:18
Yeah, and you can go to www.assemble.fyi. So for your information.

Kate Adams 28:24
Oh, cool! All right, awesome. Yeah. Well, Cortney, it was just a pleasure chatting with you. What a cool story, and I love what you’re doing with education. It’s very inspiring.

Cortney Woodruff 28:35
Thanks, Kate. And yeah, we have to bring you in and let you.

Kate Adams 28:38
Yeah, we’ll have you back in a year or two, and you can tell us all the cool things you’re up to then. It’ll be neat.

Cortney Woodruff 28:45
Let’s do it. I’m looking forward to it.

Kate Adams 28:46
Yep, for sure. Thank you.

Cortney Woodruff 28:48
All right, thanks.

Outro 28:48
You’ve been listening to Startup Success. To make sure you don’t miss out on future episodes, subscribe to the show in your favorite podcast player. Like what you hear? Tap the number of stars you think the show deserves in Apple Podcasts. For more tools and resources for your own startup success, check out BurklandAssociates.com. Thank you so much for listening. Until next time.