Startup Office Hours on Failing Forward – Audio & Transcript

A huge shout out to Derek Homann and Jina Hwang, Ph.D. for being so candid about their personal experience as founders. Lots of lessons that we can all benefit from.

August Office Hours Audio Replay
Audio from the Startup Office Hours on Failing Forward recorded on August 22, 2023.

This is a transcript from the August edition of SPN Startup Office Hours featuring Derek Homann and Jina Hwang, Ph.D. Our topic was how to handle failure and foster resilience as an entrepreneur.

STEFANIE: Alright. Hello and welcome everyone. I am Stefanie Monge, editor at Silicon Prairie News, and your host today of SPN Startup Office Hours sponsored by Elevator. I have two very special guests with me today to have a candid conversation about failure and what that means in the life of a founder, in the startup world. And really recognizing that setbacks are part of your journey to success.

I think for me, personally, I feel like if you’ve never failed, then that just means you’re not really trying big, audacious things.

[00:47] So, Jina, I’ll hand it to you first to introduce yourself to our audience today.

JINA: Yep. Thanks for having me. My name is Jina Hwang, and I am an entrepreneur. I started a company called Job Share Connect back in 2019. And I will get into the journey of that. I am currently on to my second venture with NMotion that will hopefully produce a new category company.

[01:26]  STEFANIE: Excellent. Thank you, Jina. And Derek, will you introduce yourself?

DEREK: Sure. I’m Derek Homann. I’m the co-founder and COO of a company here in Omaha called Workshop. We make internal communication software. And previously, I started another company called Median, which is a small two-person, bootstrapped company with my partner, Ben, who also works alongside us here at Workshop. He’s one of our co-founders. And before that, I worked for a number of tech companies and in startups for a while before that before actually jumping in and doing it myself.

[02:06] STEFANIE: Awesome. Thank you, Derek. So we’ll just go ahead and jump right in, and whoever wants to can start. So let’s just talk about a time when things were not working out the way you planned. And tell us how you navigated that situation? Or how you handled it?

DEREK: I’ll go first. So in my previous company, Median, I feel like there were a lot of failures, like every day. If you’re running a startup, you’re trying to learn. Some stuff is gonna work, and a lot of stuff is not gonna work. But, you know, some hit harder than others.

Immediately, we had this one instance, where I remember being super down in the dumps about it. I, we, had a couple of potential customer meetings that for us would have been a huge deal. And we had white labeled our products to other technology companies. And there’s a small number of people that could potentially be customers, and if and when we land those customers that end up being a meaningful portion of our business.

But as a bootstrapped business every dollar at that company was either mine or Ben’s out of our own pockets. I remember traveling out to San Francisco. I had two really big deals that we were working on to try and get closed. And literally, I flew out there on our own dime for a really quick turnaround — like a two day turnaround. I had three meetings, one of which was just with an old buddy. And the other two were these meetings, and I literally fly out there and they both cancel on me while I’m there. And I just don’t have any meetings. 

I just flew out there and they both just didn’t care at all that they canceled on me. They’re like, oh, we’re busy. Even though we had to schedule, we had already followed up, made sure that this is gonna be a good time. And I remember just being like, what am I even doing right now. I fly back home accomplishing nothing. Spending, you know, $1,500 on flights and hotels and food and stuff while I’m out there. Only to just go have a happy hour with my buddy who worked out there. Which was fun, but it felt like such a waste of time and a waste of money. 

Beware of putting all of your eggs in one basket

And again, we had very limited money and then literally neither of those deals closed. And there were a number of stories like that where you’re putting a lot of eggs in that basket and you feel like it’s going to work and it just didn’t. And I spent like a day or two feeling s***** about it. And it’s like alright, business still has to operate. So you go back and you just keep trying.

I mean there’s like 100 of those stories like that. I just remember that one really viscerally. Being like, alright, if I’m going to fly out there, we’re going to meet, right? And then we’re going to close this deal. And we’re like, yep, everything’s good. Everything’s aligned. We got all our stakeholders going to be there. And then an hour before the meetings both of them: Hey, can’t meet. We’re gonna have to reschedule.

That’s it. No, sorry. No, anything. It sucked. This stuff happens all the time.

STEFANIE: I mean, that’s rough. And I think that “all of your eggs in one basket” kind of mentality … As a founder, you are always going all in. You always have to be super confident and believe in yourself. So it can feel in the moment, for sure, devastating when things like that fall through. And you’re right, it’s like something that, Derek, to you, is the most important thing happening for you right now. And for these sales prospects, or whoever, it could just be like, Nah, whatever.

DEREK: I just had 100 other people that I was gonna go to, like, oh, on to the next one. We had a pretty highly concentrated number of folks that we could sell to, and just having two of them basically blow you off in the same day, after putting a lot of time and effort into it. And then just literally sending a one sentence email to cancel on you while you made a trip halfway across the country to meet them. It feels terrible.

[06:26] STEFANIE: Jina, tell us, do you have a story or an example that you can think of a big downer?

JINA: Yeah, I have a lot of those stories, as well. I would say the biggest one that comes to mind, there are a lot of parallels with what Derek was talking about — putting all your eggs in one basket. So Job Share Connect started in 2019, pre COVID. We were trying to help companies attract and retain top talent by looking at a different talent pool. And by helping employees to be able to have flexibility options outside of the nine-to-five. We got a lot of really good feedback. And we were winning grants and competitions and pitch competitions, they were in SHRM’s workplace competition. We’re getting all this good feedback.

To my co-founder, and I, obviously, we thought it was a great idea and something that would work out. So we went all in. She was working … a full-time job. I had 2-year-old twins. And we just went all in and made some progress. We were generating revenue, and made some placements locally here in Omaha.

It felt like we talked to every single company and after pretty much every single meeting I was like, you know, I think they really liked it! I think they’re gonna do it! And then being blown off by email, like, “let’s reschedule” or “we’ll come back to it” or “we’re working on something else, so we’ll get back to it.” So you know, lots of those stories. But I think the biggest one, and kind of the one that put us over the edge was one where we literally put all of our eggs in one basket.

Because job sharing is a relatively new concept, there weren’t a lot of companies that wanted to be early adopters, and were always wanting to be fast followers. Get in, get an enterprise company, and we’ll definitely come back and circle back and look into it. One of the things that they tell you, when you’re getting your first customers is that rather than you having to follow up and kind of chase them down, that they will find you and seek you out. We’d never had this happen before.

We were roughly two and a half years in and we had one of the largest health care systems in America reach out to us and that were going to work with us and were going to do a pilot. They also had an accelerator with their program. For such a large organization — it was over 50,000 people — to get some contract signed, we got it passed on to all of the parties that were needed to be involved with legal and got the contract signed in a month, which for big corporations is, wow, unheard of.

So they literally were knocking on our door, the CHRO is like, we want you to work exclusively with us. When we got off that call, we were like, oh, what just happened? Like, Oh my God, I think we just made it! You know, so super excited. We ended up starting to work with them and brought more people onto our team to get ready. And then right before our pilot, they had some organizational issues and some restructuring and put us on hold, and then put us on hold again, and again indefinitely.

And that was kind of like, our OH, F*** moment. Like, oh, my gosh, after all this in the sales cycle — for job sharing is one to two years. We really didn’t know what to do. And that was really, um, you know, a time of going back and saying, is this going to work? And let’s look at the data, let’s reassess, and try to figure out how to move forward. Hmm.

[11:27] STEFANIE: Thank you both for sharing those examples. So what did you learn from this process? What were your takeaways, when you thought about what happened and reflected on it?

JINA: Yeah, I think there were so many throughout the process. I’m not a tech founder. And I had never started a company before. My background previously was working internally at organizations in talent management departments. I’m an organizational psychologist. And so I kind of did that climb the corporate ladder and then worked as a consultant. So I did all that, and then this is my first time going out and doing this and felt really passionate about what we were doing. We found that there was a real need for it. 

Timing is everything

Just because something is a really good idea, doesn’t mean that it will translate into an actual business. There are factors that are involved. I think, one for us, and probably one of the main reasons why Job Share Connect is — we haven’t buried it, it’s kind of on ice — but one of the reasons is timing. During this time, we started in 2019, we went through COVID. And actually really thought that would accelerate what we were doing. Which it did in a lot of ways. Now we have remote and hybrid working. But I think that kind of took the place, and was kind of a pacifier for companies and for employees in saying: we check the box for flexibility, and we’re done.

The job sharing, it was just so new. It’s really about changing mindsets and changing the work model, basically. So there were a lot of really big components to what we were doing. And I think ultimately, that timing was really big. Hopefully, maybe in seven to 10 years, I think there’ll be more of a market for job sharing, and companies and leaders being more open to that. Even location, being in the U.S., there were a lot of obstacles that we face that a lot of other countries didn’t, such as health care benefits and legislation for flexible work.

I think just looking at all of those things, there’s not one thing in isolation where you can say yes, if we had done this, then it would work. You’re learning along, you’re learning as you go, and you’re pivoting. We pivoted once after COVID. And then we pivoted back. You’re just trying to read the market and trying to figure out what to do. And sometimes it’s just the conditions aren’t right.

[14:45] STEFANIE: Mm hmm. Yeah. I just want to reiterate something you said. It’s possible to have a really great idea and still not be able to make that into a viable business for a variety of reasons. I think that’s an important thing to remember. Derek. I mean, what about you? Like, what were your takeaways? What did you learn walking away from that?

DEREK: I think there’s this weird mix of like, being optimistic as a founder, but also being realistic, that you need to get kind of balanced. So you’ve gotta be cautiously optimistic. You probably need to have a Plan A, Plan B and a Plan Z. My main learnings were the highs are probably never as high as you actually think they are. And the lows are probably never as low as you think. Maybe they’re the lowest? But I also don’t trust anything until it’s signed on the dotted line now.

Get excited about the process, but stay focused on the end goal

And so I think trying to be more level headed, when it comes to those things was the biggest thing for me. The meeting isn’t actually the exciting part. The exciting part is when the thing gets inked in and you see success with them. It’s kind of reframing in my mind what success actually is, versus like, the steps along the way. The steps along the way are exciting and should be celebrated, as well. But a lot of times, they’re so far from the actual goal that it can be easy to get wrapped up in the meeting or the pilot or whatever. It’s reframing that.

Alright, I’m not gonna get too excited that some big company wants to talk to us. I’ve talked to a number of big companies and you get really excited. And then for a lot of reasons, they can’t move forward, because they’re big and stodgy and have a lot of red tape and all that stuff. So try not to get too wrapped up in that because it’s just not good for your mental health to get so excited. And then just feel like you’re getting cut down like every other day, when inevitably, you just run into the red tape that big companies have. That’s the biggest thing for me.

It’s just trying to be more even-keel about it. And understanding, you may not think another big company is going to come along or whatever. But if you stay alive long enough, good luck happens, as long as you keep putting in the work. Or at least good luck is more likely to happen, the longer you stay alive. The biggest thing has been try not to get too, too excited about it until I get a real real thing. Yeah.

[17:36] STEFANIE: So you’re saying if you can stay alive long enough, then you can increase the chances of good luck or success. So how do you stay resilient? How do you continue to keep pushing through, when it feels like a slog? And that’s for either of you. I’d love to hear what’s worked for you in the past.

DEREK: I had this in most companies, even Workshop. Today it’s doing very well, but for the first year, we were just flat and we went six months without adding a customer at one point. And we actually lost a customer. We pivoted our product multiple times. It was always kind of focused around internal comms until we really found our footing. And it just felt not great, because you’re like, Oh, like this is the second time. I will not make any of the mistakes we made the first time and you still make some of them. And then there’s just new challenges or whatever.

But there is some amount of just like not giving up gives you a better chance of success. But there’s also no guarantee that you will have success. And in some ways, it’s a gut feeling … I don’t have a great framework for this other than you can’t make people pay you money. You can certainly try to do the right things that would make them want to pay you money. But you can cut expenses. If there’s anything in your personal life that you can sacrifice that you don’t need to help you lower your personal burn or anything like that. That certainly helps.

With my first company I was in a lucky position where I had literally been wanting to start a company for 10 plus years, and I just saved a whole bunch of money and even then I didn’t spend any money. So I was like, alright, I’m planning on not paying myself because I don’t know how long it’s going to take to figure it out or if we will ever figure it out. And so that helped me personally be able to do it. I was in a privileged position to be able to do that.

Grit over everything

Honestly, if you looked at our company two years in, it wasn’t a success. It wasn’t a success until the very end when we ended up having a pretty cool series of events where we ended up selling some of the technology and getting acquired by some interesting companies. It was only because we stayed alive long enough. I made enough connections with different people that when we got to the end that it worked out. We had success, but there’s plenty of people who haven’t and went through that and good luck never happened to them. The only way that it’s going to actually happen is if you keep going. And it’s hard when there’s no guarantee. That’s the challenge.

[20:29] STEFANIE: Yeah, there are no guarantees in entrepreneurship, for sure. So Jina, are there things that have helped you to push through or keep going in those hard moments? What have you done?

JINA: Yeah, I think personally one of my greatest strengths is my determination and grit. If someone said I couldn’t do something, then I would try harder. With this, you are constantly digging for that. And like Derek said, just being, you know, cautiously optimistic, but being realistic as well. After four years I feel like we basically talked to every company in Omaha. We feel like we did try different pivots. Yeah, we could have gone on and did another campaign or kept going. It really was just stopping and looking at the data and looking at the numbers. After four years, is this where we should be? And what’s the trajectory? And also what’s the personal burn rate of doing this full time?

There’s lots of those factors, too. Part of our realization was that there were other companies that came before us, who were in business when we first started and then went out of business. I started doing a lot of due diligence and contacting them. One company was in Australia, and calling them and saying, what happened? What were your issues? And trying to figure out, are we doing something wrong? We had a very similar approach. We had some tech folks working with us who were doing it on the side. They had a full-time person who went to MIT. So they had all the technology.

And we kept thinking, well, if our technology was there, if we just keep working on that, then everything will come together. After learning from them and their experience, because that’s what they thought, too, and they had it and it still didn’t work, then it’s kind of reassessing. And, the timing, too. Actually, one of our main competitors just pulled their plug about a week ago. And, and so what I’ve said before, it’s about location and if we had this legislation in place, if we had benefits, it would work. And it didn’t work. So then again, it’s looking at all the information around you, asking people who have done it themselves specifically in your industry.

I know that that can be kind of challenging if you’re competitors, but I truly think that with job sharing, I think, rather than being competitive, we should have all of anyone who’s remotely interested in job sharing, we should have all gotten together to try to get this thing going. It just needs so much more than one or two companies behind it. Because like I said, it was a whole shift in mindset and a different work model. So I learned a lot from others, and testing out my theories and ideas by their experiences, too, rather than having to go through it ourselves. 

Inventing a new category is boom or bust

DEREK: Yeah, one thing that’s interesting there, too, especially like on Jina’s side, when you’re kind of like inventing the category is if you can invent the category, it can be huge, right? You don’t know what the limits are. Which is awesome. Like with Airbnb. There was no industry for sharing of homes or whatever. But there are tons of people that tried to do that. And it obviously doesn’t work. So like, you know, a lot of people who are doing these sorts of things … We make internal comms software — we’re not the only people that make internal comms software, there were many that came before. So there’ll be many that come after us.

But you can look at the market. There is some size of that market, it appears to be growing at a pretty good clip. If you can execute, if you’re No. 1 of the market, you make a ton of money. If you’re number five, you still probably make a lot and number 10 might actually even do fine, too. But in creating a brand new market, they’re going to be worth a bajillion dollars when you IPO or you’re going to be worth zero. It’s less in between, in my opinion.

You can’t just completely brute force it. There’s so many factors outside of your own company even to try to legislate. Like as a small company you’re not just going to create new legislation, right? It’s difficult. But if those things fall in your favor, and you’re there and ready to capture it, it can be huge, but it’s a risk. Starting companies is a risk period. And it’s a risk-reward. The challenge is you don’t ever know. 

Knowing when to cut your losses

[26:20] STEFANIE: That’s a good segue. I’m acknowledging that failure, I’ll say this in air quotes, because I think you either win, or you learn … I love that quote. Failure. I don’t know, what does that mean? That was just a really long bumbling way to say: Screw failure as a concept. I don’t exactly believe in it. But how do you know when it’s time to quit? How do you know? Jina, you shared some really great examples of the criteria you were using, when you were deciding whether or not to put Job Share Connect on hold. Anything else, Jina, that you want to add? Or Derek? How do you know when it’s time to just cut your losses and try something else? 

JINA: For me, I still have not completely given up on Job Share Connect. Like I said, I do think in time the work continues. I feel like the work that we have done was planting seeds. And now, I’m talking about job sharing, and it’s something that I still am very passionate about. One of the main things that I’m focused on now is education for both companies and employees. I think that is a piece that was missing beforehand. We were trying to do everything at one time. And we were missing, you know, that key component of just people understanding what job sharing is, And knowing that it’s even an option.

So I have not completely given up on it, I’m still continuing to educate. I go out, and I continue to do conversations like this and do panels. But ultimately, just deciding on what you’re getting out of it, and what you’re putting into it, and if it’s worth it. But with Job Share Connect we had worked on our platform and spent years and a lot of money doing this and a lot of work. So it was trying to figure out if there’s a way that I can repurpose what we’ve worked on and so then I pivoted again. We were matching job share partners, and then I pivoted again into matchmaking for romantic relationships. There’s a lot of parallels there, too.

I can’t even emphasize how important timing is because I feel like I was really close to creating an MVP for Heart Share Connect. Then this opportunity came up with NMotion for venture studios, and was kind of like, I don’t know. I think that this is a good idea. And then it’s viable, and I want to go for that. But also, here’s something else, too, that doesn’t come around every day … 

Rather than putting all my eggs in one basket, I did a complete 180. I’m going to have all these baskets and I’m going to be able to pick which one works out. That’s where I am now. Starting with back to the very beginning with ideation for Heart Share Connect. Is there something better or something that is more viable, or something that I’m better suited to do? That’s more needed in the market than what I was doing previously? You don’t know. You think you have to really just kind of trust yourself and your gut. And some of it is luck. Some of it is timing. But ultimately, in deciding what I do, it will be looking at the data and the information. Because it’s really hard to make something happen when the numbers don’t add up, right? It’s probably not gonna work.

[31:18] STEFANIE: Derek, what about you? Any thoughts on when it’s time to cut your losses?

Derek: I would just say I’m bad at giving up. If you look at it in a certain way, my previous company ended up being successful in the end, but along the way, it wasn’t super successful. Instead of just closing it down, we kind of reframed: What would success look like? What would be a good ending for this? And so we started building other products, and we started doing these other things. But through a series of events, we ended up getting in some conversations where we’re like, alright, we have really valuable technology. It’s hard to replicate. We know that there’s at least some people who are interested in it.

You can always redefine what success looks like

Instead of winding it down, and just getting a real job, we’re like, alright. If we’re going to go through the acquisition route, let’s look at what potential acquirers will look like. We don’t need to sell it. We can keep going. We have a product that makes money. We could make more money just getting a job. But so for us, it was just like reframing if outcome A, Plan A didn’t work out — we thought you’re going to make $100 million a year in this thing, and it’s gonna be huge, and you ring a bell on Wall Street or wherever. That’s unlikely now, but what is a pretty good outcome?

Or what would be the next best thing? What’s the Plan B? That’s how I look at it. If you have to go with Plan B it’s alright. Let’s find a good home for this. Let’s find a place where we have a nice little financial outcome or like the people who will be acquiring the company, or the technology or employees or whatever. We’re going to be good stewards of all of that. And so that’s kind of where we went rather than just winding it down and shutting it — it wasn’t worth zero. We reframed it around what would be a successful outcome in Plan B.

So that kind of went into, again, the longer we had in terms of our personal runway, the more ability we had to at least try several different things. And if we had to go to a Plan C, or Plan D, we could have done that, as well. I would have been really bummed if we just shut it down and moved on. That’s more like a personal thing with me. I actually think it’s the right move for a lot of people. I have a hard time with that myself.

Financially, it’s actually a bad move to start a company. It’s like, I’m gonna make so much money. Like, maybe? But you’ll probably make more if you just go get a real job. For me, it was mostly just figuring out how do I get something if we didn’t hit a home run. How can we get a single? And so that was the biggest thing for me. I didn’t want to have nothing to show for it. And since we had some runway, that was the thing. I don’t have great examples of I’m just gonna call it quits. But we probably should have if we’re being real honest …

[34:48] STEFANIE: Thank you. It sounds like there’s an opportunity to reframe what success looks like and redefine what that looks like when you’re deciding what is the best outcome? So thinking about risk, like risk taking is something that we’ve talked about that obviously is required if you are going to become an entrepreneur. How do you approach risk taking, experimentation? At this point after maybe you’ve been burned? How do you approach that now? And how do you keep convincing yourself to take risks, even when you continue to know that the outcome is uncertain?

Getting comfortable with risk

JINA: Throughout this whole process I have really learned how to be more of a risk taker. I’m naturally pretty risk averse. My mom was always like, don’t do that you’re gonna get hurt. Always doing the safe thing. And with Job Share Connect, I think that in some ways hindered us because we didn’t take VC money. We got grants. We were in pitch competitions, and we were generating revenue. It wasn’t a lot, but it was enough that we felt like, we can do this on our own, and we can bootstrap it, and, and we can make it happen.

Looking back we really could have moved further and faster, had we taken that risk, and gotten more money. I think looking back now especially with this company in the UK that just folded, it’s like, well, maybe not. But again, you just don’t know. Along this whole process, I’ve learned so much. When I first started, I didn’t know anything about anything. And so it was just a huge learning curve. Throughout all this I think we were really cautious about — we’d read all the books and listen to all the podcasts, and we’re like, oh, we’re not going to make that mistake. We’re not going to make that mistake. Here’s how we’re not going to make that mistake. And we ended up making all those mistakes in a different way.

DEREK: Same.

JINA: With our technology, we were really cautious. We’re not going to build something that later we’re going to have to change. So we were really cautious about making sure that when we start, we really know what we’re building and build from there. It just doesn’t happen that way. Nothing works that way. For me, now, I think having gone through that, you just never know. It actually makes me want to take more risks. I think it’s just changed. Going through this process has really just shown me that you don’t always have to know what’s next. But you just keep swimming, and you keep going and you just try to do the next right thing. And hopefully, things will align and it will work.You have to continue to take risks.

It has to be for more than the money if people want to start a business because they think they’re gonna make a ton of money. Unfortunately, the probability of that happening is not very likely. And also, it’s a s*** ton of work. It’s super stressful, and it’s really hard. And you have to be really deliberate. And it has to be beyond money. There has to be something inside you where you are compelled to do something that you are really passionate about. And I think that’s what has really driven me.

I could go back to a cushy corporate job tomorrow. But that’s not what fuels me and that’s not what I want to do. So I will just continue to do this as long as I can. And again, you know, if the time comes and it’s no longer feasible, then saying I gave it a shot. With failure, I think there’s such a …  I’m glad you’re doing this topic because people don’t really like to talk about failure. Or even say that. I have two young kids, and I’m always telling them you have to at least try something. One of them is just always afraid she’s going to fail, so she doesn’t even try anything. You really don’t know what is possible, or what you can do until you try.

[40:36] STEFANIE: Thank you. Yeah, that’s a powerful point. Derek, what do you want to say? Do you have any thoughts on what you’ve learned from failing? Or how you continue to embrace that culture of risk taking? Or even, how do you foster that on your team? It sounds like that you are pretty comfortable with risk, Derek?

DEREK: I don’t know. For me, I think, worst case scenario is I just go get a real job. Right? It was when I started my first company, and it was five years and some change ago. The economy especially was great. At that time it was really easy to get the job. And I had a skillset that I felt confident that I could go get one. That obviously is slightly different now I know. More tech companies have had layoffs and that sort of thing. But I still feel reasonably confident because I have low personal burn and now I’ve been in a situation where I have more of a nest egg to fall back on even if hard times were a thing. I always just felt like I can just get a job if I need to.

I don’t want to do that, but I can just get a job. The risk actually felt like a lot less when Plan Z is always just gonna be get a job if it doesn’t work out. You do lose time if you spent a year or two or three working on something. It doesn’t feel great to lose that time. But I can just go back to work at a big dopey company or whatever.

But yeah, so to me it felt less risky when I thought about it that way. I’m a lot more risk averse in my personal life than my partners. When I started my first company, I was 34. I had my second kid on the way. I wasn’t going to start a company unless I felt like my personal expenses were going to be taken care of in the event I couldn’t pay myself for a long time. And so we were lucky enough to be in a situation where we could do that.

But I wouldn’t have started the company if my wife didn’t have health care. And if I didn’t have a nest egg and all this other stuff. Whereas my partner, Ben, was like 24, he’s 10 years younger than me. And he’s like, I have no kids, I have no personal burden. All I have to do is work. We were at different stages in life. But his thing was like, you know, de-risking it for him was the fact that he just didn’t have a lot of responsibilities outside of the company. And de-risking it for me was I’m in a good spot financially and in a good spot with like health care and other things, that I can do this. And I have a resume that will allow me to get another job easily.

So it was completely different stories for why we felt that way. It didn’t seem as risky on the personal side. I wouldn’t have done that at 24. I was like, I don’t have any skills. I don’t know anything. Like what am I supposed to do? And he was the opposite. So it’s a little different strokes for different folks sort of thing. But yeah, that for me, having to have all that safety before I could take the jump versus him was like, who cares? Like, I might as well be my first foray when I’m 24. Because what else am I gonna do? Right?

JINA: You know, when I was going to school, we didn’t have entrepreneur programs. Looking back, I would have done a lot of things differently. I would have worked for companies so that they could pay for my degree. There’s lots of different things and I think that when I was younger, there weren’t all these accelerators that are on site. You hear these stories about people living together for a few months and not sleeping and doing all these things. There’s no way you can do that with kids. That opportunity wasn’t a route, or maybe it was when I was that age, but I didn’t know about it. And I certainly didn’t think that I would be going into entrepreneurship. It just wasn’t even in my realm of possibility. Looking back, I think that would be a lot of fun. I probably would have taken a lot more risks.

DEREK: I do think there’s a lot more programs and money available and things like that now, for people who want to start up. But yeah, I felt like when I was 24, there might have been seven, but I also didn’t know about them.

[45:42] STEFANIE: Right? Yeah, I think we’re all a similar age, and plus one to everything you’re saying. Yes. So we’re just about at time. I wanted to give you the opportunity for any final words of advice for current or aspiring founders who are struggling with failure or struggling with the idea of failing?

Final words of wisdom

DEREK: I’ll say it, this s*** is really hard. Even if things look amazing from the outside, I think the number of entrepreneurs I’ve seen, myself included, where on the outside things look all bright and shiny and sparkly, on the inside, it’s held together with string and duct tape and all that s***, is 100% of them. All, literally all of them. I think sometimes it’s really hard to not put on the facade, like, everything’s great, blah, blah, blah, things are going amazing. Everything’s up and to the right. It’s awesome and my life’s amazing and whatever.

It’s not. It’s f****** hard. And I think people need to know that and be more real about what that actually means. More good things can be happening than bad things. That’s generally what you want in a company — you have more good things that are happening than bad things. That’s good, but there’s still a lot of bad stuff. And it still sucks.

I lost my hair before I had ever started the company, but if I had hair, it would be gone by now. I cannot stress enough, it is really f****** hard. And you can’t spend a lot of your hours outside of your work hours … it just takes up so much of your time and energy and thoughts. There’s not a day goes by that it’s not like 11 o’clock at night, and I’m laying down to bed and I’m not thinking about some random work thing. I didn’t think that when I was an employee at another company.

It’s just always there. It’s really hard. But when things go well, and if things get aligned, it can be really, really rewarding and fun. And there’s nothing else like it. So with both of those sides of the thing, just know, it’s really hard, but there’s nothing that can beat it either. Because if you do have success, that’s your success, right? It’s not like you just joined a company that was growing super fast. It’s not like you’re employee 500 at a company that eventually IPOs. No offense, but you probably didn’t do a heck of a lot compared to someone who was the one or two or three people sitting around the kitchen table trying to get something off the ground.

That is really hard. If somebody has ever started a company and collected $1 of revenue, I can tell you that is so much harder than almost any job that anybody’s ever worked. So I think people need to be aware that it’s a really admirable thing. They have my respect for just like actually doing the thing because most people don’t and a lot of people will cast stones, too. But they won’t actually do it themselves. So it’s hard, but it’s awesome.

JINA: I agree. The highs are super high. The lows are super low. But there’s just something about it. And, you know, once you get that bug, it’s really hard to go out to get outside of that. But one thing that I will say is that yeah, it’s really hard. But I think one of the things that I’ve learned and something that I’ll continue to do is, being vulnerable, being transparent, and finding other entrepreneurs who are going through the same things for support and for advice. I’ve talked to Derek several times about things in the past and he’s been a great resource for me. 

And there have been conversations where you’re completely deflated, and you can go and talk to someone and one of their stories or some encouragement that they’ll have for you will carry you along until you can, you know, take the next step. That’s just so important. And that’s probably one of the main reasons why I decided to go into an accelerator program is because of the community. I had a co-founder who I love, and we worked great together, and I really miss that interaction. Being a sole founder is, really, I mean, probably the hardest thing you could possibly do. And that I just think that that community and that support is so crucial. So seeking those people out and finding those opportunities, is probably one of the things that makes you or breaks you.

STEFANIE: Yeah, a plus one to that! Being a founder can feel so lonely. So knowing that you are not alone and your experiences, whatever they may be, odds are someone else has navigated those challenges. So finding those people who can help share in that with you can be a really powerful thing to help motivate you. So thank you both so much for your time today for your candor. I think the TLDR is this is really f****** hard. And we do a disservice to aspiring entrepreneurs and founders when we just pretend that it’s only the highlight reel. So thank you both for sharing today. And I appreciate you so much. Thank you. Thank you.


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