Your Biggest Vision Ep. 69- Darrell Silver, Founder and CEO of Thinkful

Thinkful is an online coding bootcamp startup… that was recently acquired for a cool $80 million by Chegg.

 

Join host Leah Gervais as she sits down with Darrell Silver, co-founder of Thinkful, to hear the behind-the-scenes of building a company from nothing that just underwent a spectacular acquisition. 

 

Darrell shares TONS of marketing and entrepreneurial nuggets in this interview, including:

 

  • The framework on successful sales like you’ve never heard it before, and how it can transform your sales!
  • Darrell’s practical advice on how to make room in your life to take more risks.
  • How to tell if you’re doing your job totally WRONG as an entrepreneur (it’s not what you think!)

 

Tune in to episode 69 to hear Darrell Silver, founder and CEO of Thinkful, talk about a framework on successful sales like you’ve never heard it before.
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Transcript of Episode

Leah Gervais: Hey visionaries. Welcome back to the your biggest vision show. I’m your host, Leah and today we have Derrell Silver engineer, CEO and co-founder of Thinkful here with us. Hey Darrell, thanks for being here. 

 

Derrell Silver: Thanks for having me. 

 

Leah Gervais: My pleasure. I’m really excited to hear from you. So a little bit of background before he tells his story. Thinkful is an online coding bootcamp and it prepares its students for a career in tech from a standpoint of innovation, empathy, accessibility and a true passion for their futures. Derrell ons, thankful with his co-founder, Dan in February of 2013 based on the idea that education should be available to everyone. And just last week it was announced that Thinkful was acquired by Chegg for $80 million. Congratulations. 

 

Derrell Silver: Thanks very much. 

 

Leah Gervais: Yeah, absolutely. So let’s rewind a little bit. I’m sure that the last few weeks I’ve been kind of a whirlwind for you. Did you want to be an entrepreneur when you grew up or did you want to be in tech and you became an entrepreneur from there? 

 

Derrell Silver: Um, none of those things. I fundamentally had a lot of sort of easy time getting to know tech. My parents were very supportive of me just exploring other things. And at school I was supported to explore random things and I was always into computers. And then in high school I got into photography and then photography at that moment was turning digital. And so I got back into computers and then I started becoming a coder so I could organize my photos. After college, I worked in finance and I found it quite fun on a day to day basis but not fulfilling long term. Yet again, I was, um, fortunate enough to, to, to be able to leave that job and try something very, very risky, which I’ve since learned is very, very rare. Um, most people don’t get that kind of opportunity. And, and um, that was, that was a decade ago. It was more than it was 12 years ago. So, uh, I’ve been in this career now for 12 years. This is my second company. Um, uh, and it’s just been hard work, hard work, hard work, perseverance. Since then. 

 

Leah Gervais: I’m sure. Where are you from? 

 

Derrell Silver: I’m from New York and my parents are still here in Manhattan. Uptown. 

 

Leah Gervais: Okay. So this is the second company. This is the second company you’ve founded. Is this the second company that you’ve had acquired? 

 

Derrell Silver: Uh, it is, yeah. 



Leah Gervais: Yeah. The first one was acquired by Dell. Right. Actually think I remember reading about that. Yeah. Congratulations. So walk us through a little bit what it’s like to go from being in the tech world to then, you know, I think it’s a very different role to be someone who’s a coder or developer to them being a leader and someone who hires people and trains people. And how did you deal with that? 

 

Derrell Silver: It’s definitely a different role. It, uh, definitely takes a kind of humbleness, but most of all it takes, I’ve just a perseverance to every single month and face new challenges every single month. Be creative about how to solve a problem. Um, you’re not really an entrepreneur until you’ve woken up and not been able to sleep through the middle of the night trying to figure out how you’re going to make the next payroll. You’re not really an entrepreneur unless you find yourself completely unprepared for something that’s life or death or feels like for death. You’re not really an entrepreneur unless you’ve, uh, felt like you were resting on your laurels and existing skills for six months and now realize how far behind you feel. So all of those things are true. And it’s true in the transition from becoming from a software engineer, uh, which is such a focused and in its ideal state is such a focused endeavor. And it’s such a, it’s such a small team endeavor to being something where you talk in abstraction or you talk in a motivation. Are you talking division? And, and, and hire people that are, that are aligned with that. Um, and that transition is like, this is one of the many kinds of things you have to, you have to get used to in it. If you’re gonna, if you’re going to grow with a company. 

 

Leah Gervais: So you said you grew up around tech and it was very accessible for you to learn tech. Do you feel like there were signs now looking back that you had an entrepreneurial bone in you or that you were meant to do this? 

 

Derrell Silver: Yeah. Well, I don’t know about [inaudible] I meant to do it, but certainly, um, with thankful of the last seven years, what I’ve realized is that very, very small number of people have the exposure at a young age and the freedom through adolescence and adulthood to explore things like entrepreneurship. So for me, I think of it as less of, um, less of- sure, like I worked very hard and all that. Um, but, but fundamentally, uh, the world was kind of set up for me to be very risk taking in my career. And it’s easy to think that it was like, because of the hours you put in this job, it’s easy to think like you’re the one who persevered and you’re the one who succeeded as a result of all the work you put in, which just sort of true. But it’s also true that that debt that I had, um, the opportunity to do that, which a lot of people don’t have. 

 

Um, and that’s the, that’s even the rare part. So the perseverance is rare, but, but, and I wish more people had it and we sort of think about how to train it, but, but fundamentally I wish the world was more allowed, more mistaking. And so when I look back through my education in elementary school, I was in a school that was very free form and allowed me to allow me to, uh, push on boundaries. And they had a computer lab that had, um, and nobody’s going to remember this, but a computer lab had Apple 2E’s, uh, which are like the precursor to the Mac. And then at some point they upgraded to the Mac and they had still wanted all the lesson planning to be done on the Apple 2E software. So they put a, what’s called an emulator on top of the Mac to make it look like one of these old computers. I was like, that’s crazy. And it’s this eight year old or whatever. I was like, this is crazy. So I figured out how to like get rid of the emulator and work on the Mac, which is this brand new fancy technology at the time. Um, and so part of that is me and I deserve a little bit of credit, right? I was pushing boundaries and all that, but most of that is actually that, um, number one, I was at a school with Apple 2E’s. Number two, I was then at them school at the same school with Mac, which is crazy. Number three, I was given the freedom to sort of break the Mac and break, go outside the lesson plan, which is extraordinary. And then number four, I didn’t get any trouble for that. And in fact it probably would probably, I don’t remember it personally. Probably what happened is I was basically supported and that kind of exploration and that kind of stuff is so, so rare. So, yes, I did a lot of work, but, but, but actually the, the, the vast majority of what I was, um, enabled for came, um, through advantage advantages that I just got lucky on frankly. 

 

Leah Gervais: Do you think, so if someone’s listening to this and they are excited by the concept of entrepreneurship, but they either know from their parents or whatever circumstances or maybe just internally they are risk averse, do you have any advice on how they could include more risk taking into their life? 

 

Derrell Silver:  Well, um, you mean as a person who sort of wants to become an entrepreneur and wants to be, wants to be, wants to be building something that doesn’t exist? 

 

Leah Gervais: Yes, but maybe he doesn’t have the background that you had. 

 

Derrell Silver: Yeah, I mean I think so. Well, I mean that’s sort of why we founded Thinkful. It’s not really pitch, we’re thankful, but that is why we founded Thinkful is to make it low risk to get the career you find fulfilling. So, but, but I think the advice is that there’s always this balance and there’s always this sort of calm takes, this combination of having the opportunity and ability to actually afford risk. So, um, evenings to quit a job. Do you have the hours in the day after work to put toward a passion? Do you have the, um, uh, do you have literally the ability to fail? Meaning if you fail at something after six months or a year, are you, is your life able to move on in a sort of basic, most basic way? Like can you pay your mortgage, um, uh, or are you set up so you don’t have a mortgage where you set up where a significant other or partner can support you short term? Those kinds of basics, um, make things a lot easier for people. And that is very, very rare. Um, what it is also the case that that perseverance or putting in extra hours can and make that demand on those basics a little bit less. And it’s often the combination, the two. And what I find is that it just takes years and years no matter what. And so my advice I guess is, um, plan, plan, years and years in advance for having that ability to not every day is gonna feel like progress. But having that ability to see through the challenges of, you know, the last three days I wasn’t able to put any time in because my kid was screaming, but I would did about this idea and I was able to put in five hours last week or maybe it’s five hours last month and you can kind of chip away and chip away, chip away over the years. Um, and like I say, we, this interview was really nicely timed because we’ve just announced the intention to acquire Thinkful, but, but for, for sort of like, it’s this amazing event, but, but as I said already, we’re like, I’m 12 years in. 

 

Leah Gervais: Right, right. This was not an overnight success. 

 

Derrell Silver: The line in this world is an overnight success, a decade in the making. And that’s, and that’s, you know, there’s people that have far larger successes than, than, than Thinkful, than me and than Dan and other everyone else. But, but fundamentally, um, it takes a very long time and you have to really enjoy that and you have to really persevere through it. I was, um, I’m never, I’m never disappointed when I when I attribute a success to a longer period of time of work put in and it is harder for people that don’t have, um, savings or access to the technology in a very basic way or, or, uh, and that’s what thankful tries to do us to make that easier, but, but it is still reasonably possible and there’s a lot of creative ways to do that. Um, I guess the other, the more practical tip is find your community, um, where you live, um, makes it surprisingly easier to find people that are like-minded and encouraged. 

 

So the easiest way to crack perseverance is to be around people who have perseverance because they’ll influence you. Easiest way to do anything is to be around people. Easy way to make something easier to be around people who are passionate about it and they infect you with that passion. So, so the same is true with perseverance. The same is true with independent projects, same is true with start-ups, same is true with freelancing. If you’re around people who are passionate about it makes it easier. So, so find your community. I think as long, very practical piece of advice and it might feel like you’re not working on your project, but this is part of why coworking spaces is so popular. It’s part of why meetups are so popular. Part of why, um, it’s part of why there are tech centers growing throughout the U.S. around, um, uh, that are not just in New York and San Francisco directionally growing faster in places like Milwaukee or San Diego or Denver or Portland or all over the country. 

 

Leah Gervais: Yeah. It’s so funny you say that too. Later today and then getting on a flight to go work with the Wisconsin Economic Development Corporation to showcase how Milwaukee’s a great city for entrepreneurs right now. It’s really blowing up. Okay. So I love the advice in our community. I also love the advice about what you said about making your life practically risk averse. Is there anything, I’m just curious, you might not have the answer off the top of your head for this, but is there anything internally from a mindset perspective for you that helps you with your perseverance? Like what’s your go to when things go wrong or how do you pick yourself back up? How have you gotten better with failure, emotionally? 

 

Derrell Silver: Uh, that’s a great question. So, so the most basic thing is failure is part of the job. If you see it as something that’s outside, if you see it as a surprise or you see it as not part of the job, it’s that you’re doing it wrong. Like failure is part of the job. That the whole point of perseverance is not necessary when all you’re doing is succeeding. Perseverance is necessary. Failing failure is part of the job. So, when you zoom in on any professional life, you will discover periods that seemed like big successes followed by periods that were huge resets. And the resets are just failure. When you zoom into what it’s like for those periods. Sometimes I look at, um, I go to like, I go to like pictures of startups that are doing really well and, and, and they, they show the graph that goes up with a classic graphic, goes up into the right, I guess it’s from your perspective, this way it goes up into the right, um, for years. And then look at how big and great their success is. And then when you look at that graph, you can see, well, you know, from 2015 to 2017 it was sort of down actually. And then in 17 it really started picking up. And in 15 it was really doing pretty well. And it’s like 15 to 17, so it really down. Yeah. And you realize that’s two years of failure, like two years.

 

Leah Gervais: Right. That’s two years of the CEO not sleeping.

 

Derrell Silver: Right. Or the whole team trying to figure out what’s going on. So, so failure is part of the job. If you see as an exception, then you’ll, then you’ll, it’ll become an emotional, um, story. And that’s not, that’s not right. You want to think of failure as part of the journey. And um, it’s what requires perseverance. Um, uh, and then the other thing I have is a cofounder, uh, cofounder is incredibly powerful for, um, being able to level set you. Cause it’s often the case that your being, your failing is not your co-founders failing. And when it’s combined, it means that there’s something the two of you have decided to do or the three of you. So, so those relationships are absolutely key. Um, yeah. 

 

Leah Gervais: Do you have any advice on how to find a cofounder for someone who might not know where to even begin to  look?

 

Derrell Silver:  Oh, well I think it’s definitely find your community. Yeah. Um, and it starts there, but honestly I don’t, and I wish it’s a topic that people are probably smarter than me. I think I got very lucky. But I think when I think about how I got lucky, it’s, I found Dan, um, five years into that 12 years that I’m in right now. Right. So it took, so from one perspective, it took 12, it took five years, right. That whole time. But, but, but that’s the, that’s the story these things take awhile. 

 

Leah Gervais: Yeah. No, that’s, that’s great. Um, shifting a little bit to some of the things you’ve been alluding to to your values at Thinkful, you know, I know that, well, you tell me, make sure I’m right, in Thinkful you guys, you do not have an application process to your school or you do have an application process, but you do not. Um, essentially you want to encourage everyone that can join to join. Is that right? 

 

Derrell Silver: Yep.

 

Leah Gervais: You want it very accessible and then you either guarantee or promise some sort of work with your students once they graduate from your school to get a job every time. You know, you really kind of do it differently than colleges. So I think that that’s absolutely amazing. And I’m sure that there’s been, I mean, I can’t help but think, has there been a tension there at all between allowing so many people in and wanting this to be accessible to everyone and then still trying to take on this very big and real responsibility of getting that many people jobs? That’s a lot. 

 

Derrell Silver: It’s a, it’s a challenge. So, so we only admit people that we think are going to succeed but the core decision is around how we decide whether, how we decide that someone’s going to succeed. 

 

Leah Gervais: Yeah, how do you decide?

 

Derrell Silver: What we do look at is whether you’ve got a proven, like what do you show that you can actually put in the time and you’ve shown, you’ve got the beyond curiosity, but a passion for the outcome that you’re looking for, that fulfilling career. And what we don’t do, and this is what the changes from traditional system, we don’t look at test scores. We don’t look at, um, we don’t look at a pedigree or anything like that. And so when we think about open admissions, we’re trying to be open to anyone. Got the, got the, uh, passion to do the job, cause it is hard work, but we’re not trying to prejudge whether your path to getting to us means you’re more or less likely to succeed. 

 

I think the, the challenge in one of the, one of the benefits of our model is that it’s a reasonably fast turnaround for education. Now it’s a six months until you graduate, six months, anywhere from zero to over negative two to six months to get a job. But, but so the turn around isn’t that fast. It’d be like four months to a year. But, the feedback we get on our students is reasonably fast relative to a traditional higher ed system, which can be measured, which is measured more often in years. Um, and especially the ROI on that education is measured in decades. Um, and so we get pretty good feedback about whether it’s working. Um, but again, it’s about letting people, um, it’s about being able to stand behind every student or stand with every student who’s joining that they’re gonna succeed on the same rates that we see across our entire student body. 

 

Leah Gervais: Right. And you offer mentorship for all your students? 

 

Derrell Silver: Yeah, since the, since, um, since our first test cohort in November, 2012 when it was me and Dan being the first two mentors, we’ve had one on one mentorship. One on one mentorship is key for motivation. It’s key for accountability. It’s key for feeling like you can ask a question that you feel might be stupid, like all these things. Um, and so that’s, that’s sort of what we’ve done, what we’ve done. 

 

Leah Gervais: Have you struggled as scale with such high touch parts of your life? 

 

Derrell Silver: Not actually. One of the key things we did in 2013, one of the big, big questions we had in 2013 that we answered it was really key was, uh, can we find people that are motivated to be the experts and, and do this kind of mentorship? And the answer is yes. Like it turns out if you make it fun, like we don’t all that, we don’t ask people to recruit students, we don’t ask people to handle billing and lesson planning and, um, you just gotta show up and do the fun parts of mentoring, which is like the be there and you can do it part time. There are millions of people who are experts in the domains. We teach, uh, web development, software engineering, data science, data analytics and design. Like you can, there are millions of people who are experts in those fields. And if you think, do you want to, do you want to, it’s not exactly volunteering there. They’re paid, but, but do you want to kind of volunteer like five hours a week, uh, to work with students to see them grow and all you have to do is the fun part. So helping them solve problems and then seeing them succeed month over month. And the answer turns out to be yes. Like it’s a, it’s a skill that people do. Um, uh, it sort of learned a lesson that you can learn all over the internet, around user generated content, but, but there’s a key, there’s a key thing that people contribute to if you make it fun and easy for them, it’s not- haven’t had trouble with that scaling. Actually, it’s been one of the really remarkable things that we were surprised by in the early days of thankful. 

 

Leah Gervais: Yeah. Well it an amazing component to your business. I love, I love that entire concept. And so when you founded your first company, did you fundraise for them as well or did you have to, did you fundraise for it? 

 

Derrell Silver: I did. I did like friends and family a little bit. Yeah. Not much. And I frankly don’t know what those people were thinking by investing in hindsight if know what we were doing. It was, it was, it was just failure throughout. So it was exactly, that model is failure throughout and then perseverance. And the people that I worked with at that time, like my team, um, we were small, but my team, like they, they, I’m still very good friends with them and I would work with them again. So, so, uh, yeah, I don’t know what the investors were thinking, but luckily, no. 

 

Leah Gervais: So, but that was very different because I think, I correct me if I’m wrong, but one of your biggest [inaudible] for Thinkful fundraising was $40 million. Something much, much more massive. Is that right? 

 

Derrell Silver:  Yeah. Well, uh, we, we, we raised a lot less than that in practice before, um, before this acquisition announcement. Uh, uh, we’re thankful. We’ve raised I think about 15 or 16. Um, thankful. So, so, and then this acquisition announcement sort of preempted our fundraise that was underway. Um, but yeah, no Thinkful, we had an inkling of what we were doing. In hindsight, I would’ve said, um, would, gee, you really, you really had to work a lot harder than, than you might have otherwise had to, uh, in that first company because you really didn’t know what you were doing. And I wanted, my advice nowadays for people that are thinking about that is have you worked at a company that you’d want to build? Um, and so if you’re at the stage that you’d want to build it out at that early stage or at a, at a slightly later stage, anywhere from sort of five to 500 people like that very early stage of a company. Um, and I think that experience can be extremely valuable and a lot lower risk and a lot, um, a lot easier to transition from there to your own company. And I had not done that until so, uh, perpetually that first company. We tumbled through it, uh, as a result. And it was, it was, it was successful in the end, but man, in hindsight, what were we thinking? 

 

Leah Gervais: Hey, I think that no matter where you, um, start from though any entrepreneur is going to look back and have a moment of what in the world was I thinking? 

 

Derrell Silver: I will say one of the things, it’s funny actually, one of the things I always tell our our product team is the earliest indication that you’re, that you’re on something good is when you feel really stupid about discovering it because you think, gee, I wish I had done this. I wish I had done this six months ago. Turns out like the decisions that are really good are the ones who really feel like you could’ve made earlier. Um, and so, so it’s, it almost fits exactly that model of like, geez, I mean hindsight man, I really should have known. 

 

Leah Gervais: That is, that’s so true. I like to see that with my clients too. Once I, once they know they want to start doing something, I mentor entrepreneurs and once they start doing something, they’re always like, Oh, I’m just kicking myself for not doing this six months ago, but here we are. And it’s like, that’s really good advice. That’s when you know that you’re doing the right thing. 

 

Derrell Silver: You get it almost instantaneously in your brain faster than the data will show it faster and the customer will respond to it. So it’s pretty funny hack. 

 

Leah Gervais: Yeah, it’s true. Um, okay, so you go from software engineer, developer, and then you go put on your preneurial hat and then you put on a fundraiser hat. Was that unnatural for you? Did you do, did you do a lot of fundraising? I’m sure you’ve had it in the beginning. 

 

Derrell Silver: Yeah, you do. Um, a lot of fundraising and investor relations and sort of market relations and networking and all these pieces, um, they’re all part and parcel of the same job. I think what you realize is, um, every role becomes a sales role at some point. Yeah. Whether you’re selling and recruiting or you’re selling in vision or you’re selling in the market, like it’s, it’s all you’re selling. Some peers set or selling some competition, like every role becomes sales. Um, and you have to kind of be turned on by that a little bit. And I think one of the fun parts of this job is you get to really discover what you’re turned on and turned off by, um, really, in a way that in a way that matters. It’s not a, it’s not an academic experience. These are, these are people’s jobs on the line. And so you have to sort of react to what- you have to figure out what the next challenge is for your job as it evolves. And then you have to also figure out whether you’re any good at it and whether you want to be any good at it. 

 

Yeah. Have fun fundraising or the process of understanding where the market is on your product and positioning it and blah, blah, blah. All that stuff. That’s, that’s something that I’ve found. I really quite enjoyed the process of acquisition and the process of that negotiation and the process of, uh, keeping the company running while, or sort of like delegating so much of the company running operationally while you get to focus on that stuff. It turns out, it turns out it’s quite fun. Um, uh, but there’s plenty of parts of the job that aren’t, uh, that I can’t find fun. And so I try to make sure we hire people or at least I get Dan to…

 

Leah Gervais: You get Dan to deal with it. Yeah. Do you, um, do you have any tips for how to become a better salesperson or do you have a way that you feel that you’ve become better at selling? 

 

Derrell Silver: Um, advisors is one of the most obvious. So again, 12 years in you get to know some people that you think are smart. So, so one of the things I’ve noticed is, um, uh, there, there are people that make you smarter when you’re around them and there are people that don’t. And uh, it has nothing to do with those people. It’s just a combination of me and that person. Are you in that person. And so when it comes to advisors and people that can help me understand how to navigate a certain situation, whether it’s some sales or whether it’s some fundraiser or whatever else, finding those people that are, that, that, that think the way I do or that that pushed me the way that I need is very, very valuable. That combination, not everyone can do that. Um, by definition there’s different ways of doing the same job. And so you have to find the people that are, that are good for you. Um, but those advisors are incredibly valuable because they hopefully seen more than you. They’ve been through it before. They’re on the outside, so it’s less emotional. 

 

Um, you by describing the situation you’re in, you often articulate your own problem and solve it. So there’s an enormous value there. Um, and people do it. Um, don’t tell them that they could charge, but basically a lot of people do it for free. Um, and that’s number one. Number two, uh, that same idea of find your compliment, find the people that make you smarter. That’s true in the, in fundraising as well. A lot of people I talked to about fundraising, they hear no and they say I’m getting 80% no’s and it’s actually like irrelevant. If you ask the wrong person the right question, you’ll get a bad answer. So, so you should ignore all that. You should understand where their answer is coming from. Um, uh, and, and, and only listen to the people that are giving you the right, giving you feedback that’s the right place. 

 

So, understanding of process and reacting to the market is pretty important. That’s why I call it less about fundraising and more about getting an understanding of the market. Because we have, when you fundraise, you should have some sense of product market fit, whether it’s your founder to the product and you have nothing or whether it’s customers that are responding or whatever. You should have some, some definition of product market fit that works. And, um, from there it’s more about understanding the market’s response to your product market fit rather than fundraising. Cause once you understand the market response, you can then say, well gee, it makes logical sense that that money goes from that investor to my company and equity goes from my company to that investor or something or whatever the mechanic may be. Maybe it’s maybe it’s, I can understand why this customer’s getting is going to give me dollars in order for some service that they’re going to get much more value out of. And like it’s like it’s less about, um, sales is less about sales and fundraising and fundraising. Less about fundraising is more about understanding what the market is trying to do. And so a lot of that is filtering out all the noise, um, the people that are relevant to your products feature and, and, and only focusing on those that should want your product or should want your service. 

 

Leah Gervais: This is such, such good advice. There’s two things that I love that I want to pull out from what you said because I think it’s so relevant to, you know, I work a lot with online entrepreneurs, which is a very modern way to run a business. It’s all virtual. And so often they’ll come to me and they’ll be like, I know that you told me to raise my prices, but I told my mom and she just thinks that that’s way too much. And it’s like your mom is not your ideal client at all. Why are you asking your mom for advice on how much you should be charging when your mom has no idea how this can of business runs at all.

 

Derrell Silver: Yeah. The pricing is, uh, the pricing is one of the biggest areas that people make mistakes because you think you can’t imagine someone paying that amount of price and what that means that you don’t actually understand the value you’re offering. Right. And those tend to really underpriced products. Right. Especially when they’re signed to companies. Um, uh, because I just don’t understand the value offering they’re being offered. They’re offering their, their, their customer. 

 

Leah Gervais: Right. That, and then the other thing I wanted to pull out was how you said that, you know, fundraising isn’t really about fundraising. Sales ends up not being about sales in a way. It really comes down. It can be kind of seen as service. If you have a problem, I know how to fix your problem, we can have a conversation about it. And it really doesn’t need to be that much more complicated. 

 

Derrell Silver: Right? I mean, what is a startup but a search for a more efficient economy, right? So, so finding your, literally the tip of the spear for as a person doing the clinical or fundraising, you are the tip of the spear for what is the efficiency in the market that you’re creating. So if you can understand that, then it’s going to be hard. And if you do understand the efficiency you’re providing your customer, the reason they’re hiring you, um, the service you’re providing is better than what they have already. Like that’s the, that becomes a fit. The rest of it becomes a [inaudible]. 

 

Leah Gervais: Yeah. And I love what you’re saying about startups being about efficiency or about how, you know, solving a problem better than the current way they’re doing it. Because another thing, I think a lot of aspiring entrepreneurs or new entrepreneurs put this pressure on themselves to invent something new and out of the blue. And a lot of times you’re just doing something better than someone else has done it. You don’t necessarily have to like, you know, invent something that’s never existed before. It just needs to be an improved way to do it. And I think that, I’m sure that that’s why you guys did a lot. You just, you took certain bits and pieces of art existed and put them together and made it a lot better. Did you feel pressure in the beginning to yeah. What was that like in the beginning when you were trying to fine tune it? 

 

Derrell Silver: Well, um, so it’s especially true in education that everything’s been done and it’s about combining the right ingredients to a solution. I think what’s really interesting about product development and technical product development is the things that have been done. Um, you approach them differently when you’re using software. Uh, and instead of instead of process but in detail. I think the things we did at the beginning of Thinkful were we just had a couple of opinions about the way the world should work. So we said, we’ve said, uh, we, we don’t think people are gonna learn from video. We think you need one on one interaction. You think you need human interaction. Um, and then from there we just got rid of all the, we just tried stuff from there. We just tried stuff. We have to, you have to have human interaction. You have to be able to do it on your own time and it should be online cause that seems the most efficient. 

 

So you could, you could spend months planning out more, more ideas about what might work and what might not work. But we just said, well what’s the instant way to, to go from, we think it should be human interaction. We think it should be online and we think you should be able to do it on your own time. Like, how do you actually turn that into something that somebody can use and buy? And then how do we save, someone wants to buy it. It was Dan who said, well, let’s just run a class. So this was like October 15 he said, let’s just run the class by the week before Thanksgiving. That same, uh, you know, four weeks later we had a class of six people. And so you could spend months doing all sorts of forward planning or [inaudible] but like, you just get going, you just do it. 

 

Leah Gervais: Just try stuff. 

 

Derrell Silver: Let’s try it though. So we had our, we had a couple of key opinions. May or may be the right, maybe the wrong, you don’t really know. It didn’t really matter that what matters is getting feedback from people that you think you’re gonna find value in your product. So, so, um, we just, we just tried it and, and in practice we got to $500,000 in, in revenue, like an annual revenue using Google docs as our curriculum. So I had something, it didn’t work. We tried something else, didn’t work, try something else. It worked and we just kept doing it every day. We kept doing more and more of it and that led us to still using Google docs to get to half a million dollars in revenue, which is just sort of crazy. But, but it’s definitely um, the right solution. Right. Cause then when we really wanted to build a platform, we knew what we needed that stage fast. 

 

Leah Gervais: I have my last question for you and then I have a few, um, lightning round questions, but just shifting a little bit. You obviously have worked, what… I’m assuming is more than most over the past 12 years, you know, being an entrepreneur is all demanding. I fully don’t believe in the work balance concept here. Have you felt like, how, have you experienced any tension between like this influencing your personal life too much? Have you struggled to find balance or have you just kind of accepted like, this is who I am and this is what my life’s going to be like? 

 

Derrell Silver: It’s a great question. So I’ve been very lucky there as well with uh, with a husband that’s very supportive of it. I think in the last year, um, there’s been, um, so, so let me put it this way. When I started, when I was in finance, I would work so 50, 55 hours a week, um, and I was just starting to date, uh, my now husband it was 2007. Um, and then when, um, when I quit that job and started working on this other stuff, he was shocked at the number of hours I would put in. He said, you’re not gonna be able to do that. Every year it sort of ticked up a little bit. We’re not in 2019 and now he said like in a few months ago, he said, like, you work more hours than I can fathom. Like it’s crazy. So, but he’s been very supportive of it and that’s very rare and very special. 

 

And I think in 2019 we’ve probably crossed the threshold of sustainability for that. I think, um, the, an acquisition process and all that is really is really time consuming by nature and um, yeah, it has a natural ebb and flow. And so luckily we’re about to go through the, we’re about to, we’re about to come to a more sustainable moment to it now. It’ll still be 60 to 70 hours a week for the, for the, the rest of my life probably. But for that, I think, um, the cost to that are, uh, I don’t have any kids. Um, and yeah, and that that would be a change of hours put in. Now I see entrepreneurs that do that and I see entrepreneurs that do it very successfully and I’m, I’m pretty interested to figure out, um, figure out what their, what their secret is. 

 

It’s sort of like an odd thing. I can’t fathom it. But from what I understand, um, and this is another lesson I get from Dan. You have to really think about whether you’re actually on a sustainable route for you personally. Uh, and you can’t let, like maybe a month is really busy or a month is not busy. At all, but you have to be on a sustainable path, but the number of hours you work or the focus you have on work as opposed to the rest of the life. Yeah, what got bounces. Certainly real. You have to, but it’s more about are you setting up for a long term that you can be healthy with several hours, level, personal relationships level, all that stuff. 

 

Leah Gervais: Right, right. Suitability is key, but I also think for me anyway, I’ve, I’ve had my business for just over three who’s now, I worked by my, I mean I have a few employees, but it’s not like you are, you’re building, you know, several hundred employees. Um, and things did get a bit easier in the beginning. It was much more demanding I felt like. And it wasn’t so much that it was more demanding. I still feel like I work all the time, but it was just, I had no clue what I was doing. So I felt a lot less efficient, I guess I would say. Because now I can work and I know it will work. So that’s my advice also is hanging there. In the beginning, I think it gets a little bit better or a little later on. Um, all right. I have three lightning round questions for you. Are you ready? What is your go to when you have terrible day?

 

Derrell Silver:  The gym.

 

Leah Gervais: The gym. What are you most proud of so far in your career? 

 

Derrell Silver: Uh, last week.

 

Leah Gervais: An $80 million inquisition, hell yeah.

 

Derrell Silver: The moment is the moment of that last week was, um, standing in front of a room, a zoom room of a, of hundreds of people saying today is a day that you’ll be able to, um, that’ll, that’ll dramatically impact and improve your career for the rest of your career. Uh, and being able to do that was a new kind of feeling. Um, it’s something bigger than any one of us in that room. And, and being able to deliver that message was very special. So that’s the thing I’m most proud of. 

 

Leah Gervais: Absolutely. It’s amazing. Do you have a go to motivational book or podcast that helps you as an entrepreneur? 

 

Derrell Silver: Uh, I do not. Uh, I’m currently reading, um, I’m currently reading a couple of things. But I don’t actually. 

 

Leah Gervais:  Okay. And where can people find out more about you and, or Thinkful? 

 

Derrell Silver: Ah, well, Thinkful is Thinkful.com T, H I N K F, U, L and me is Derrell Silver on Twitter or just DerrellSilver.com D E double R, E double L, silver, like the metal, .com. 

 

Leah Gervais: Cool. Well, thank you so, so much for being here and sharing your journey with us. A huge congratulations on this acquisition. I’m incredibly, uh, in awe of what you built and your success and I really appreciate you being here. 

 

Derrell Silver: Thanks very much. 

 

Leah Gervais: Thanks so much, visionaries. We’ll talk to you soon. Here is to your biggest vision. Bye.




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