Most of the founder stories we hear are the successful ones, the ones with happy endings. This is not that kind of story. Being a founder comes with only one guarantee. At times, the obstacles will be so absurdly difficult, they will seem almost comical. While you can’t predict what’s ahead, you can prepare for it and you can learn a lot from Lynsie Campbell’s experiences since she survived everything a startup can throw at you.
In This Better Work, Lynsie Campbell shares the true stories of her 15-year journey through the hyper-masculine tech startup world; the good, the bad, and the ugly. She generates priceless advice that can help other startup founders make better decisions and avoid some horrible mistakes.
This is the Author Hour, I’m your host Benji Block and I’m thrilled today to be joined by Lynsie Campbell. She has just released a brand-new book titled This Better Work: A Female Founder’s (Wild) Journey through the (Hyper-Masculine) Tech Startup World. Lynsie, so glad to have you here on Author Hour today.
Lynsie Campbell: Hi Benji, thanks so much for having me.
Benji Block: Absolutely. Lynsie, for listeners who may be brand-new to you and your work, talk a little bit about yourself and your background.
Lynsie Campbell: I spent the majority of my career working in the tech industry. Started out in the marketing department of a company called Spreadshirt and quickly after that, went the entrepreneurial path and I’ve been a female tech founder ever since.
Benji Block: That’s fantastic. What made right now the right time to write this book?
Lynsie Campbell: You know, this started when I felt like I was at a pivotal moment in my journey, honestly. I had just gone through an experience with the second tech company that I had launched in 2017. After working pretty hard at it for two years, I come to the point in the journey where I had to make some decisions. As I was making those decisions, I was doing a lot of reflecting and it just seemed like the right time to pull the details together and put this together into a story and really create something that I could pass on to other female tech founders to help them navigate the journey.
Benji Block: Would you say writing this was somewhat therapeutic then?
Lynsie Campbell: I mean, I say that all the time. I really had to go back— a lot of it is a memoir. The way the book is structured, every chapter revolves around a pivotal moment in the founder’s journey. It’s things like hiring the first crew, picking the investors, meeting your cofounder. All of those pivotal moments are wrapped in my true stories of the things that I went through when I was starting growing and running two tech companies.
It felt very memoir and a lot of it was reliving the good times but also reliving the bad times and I feel like I came out the other side a different person.
Benji Block: Lynsie, I know you mentioned that you wrote this book for female entrepreneurs but talk a little bit more about who your ideal reader is and who you would love to pick up this book.
Lynsie Campbell: Yeah, this book was absolutely written for first-time female tech founders who were getting ready to start a journey and they know there are a lot of things they don’t know and they’re looking for answers. Not only looking for ways to do things right but a lot of times, when I talk to female founders or any founders, what they’re really looking for is also trying to figure out what to avoid along the way as well. I wrap a lot of that into this book.
A Female Face In A Male-Dominated Industry
Benji Block: That’s fantastic. Well, here’s where I kind of want to start. I would love for you to talk a bit about where you first got bit by the entrepreneurial bug. When did that first happened in your life?
Lynsie Campbell: Yeah, I don’t know if I ever really— I don’t have a necessarily a moment where I got bit by the bug but I did grow up in an entrepreneurial family. My uncle, through marriage, was a real estate developer. He’d grown up in poverty and, I watched over the course of the early years of my life, transform a single hotel into basically, a portfolio of hotels. I knew things were possible. I knew that if you worked hard, you committed yourself to something that you can do it.
That being said, I grew up very much a creative. I wanted to be a writer. I went to school for journalism and I think one of the things I realized early in my career is that I would just get bored. I felt like I would get to the point in a role or at a job and I was learning everything that I could [have] learned. I think that was probably the first sign that I wanted to be able to take on as much as I possibly could and learn as much as I could.
It really hit me when I started at my first tech company when I realized I wanted to work in tech. I didn’t even know it was honestly possible. I think that’s one of the things about when I started my first company, and when I grew up is, there were no female entrepreneurs. There were no female tech founders in Pittsburg that I could look to and even know that this was an option.
It was really going and working at another tech company and seeing how it was run and who the founders were. I was like, “Wait, this is something I can absolutely do.”
Benji Block: That actually being able to see it was a big pivotal moment.
Lynsie Campbell: Yeah, I say that I think women in tech— this is an issue overall as you know— you have to see it to be it and that was one of the things I didn’t have early in my career, especially in tech.
Benji Block: Wow. In many ways, also, you talk about the story of finding your cofounder and I would call that a professional marriage. You’ve absolutely experienced the ups and the downs of that relational dynamic. You had a lot of highlights at the beginning in your journey and you’ve also experienced some really hard moments. Speak to that a little bit and what your experience has been with co-founders.
Lynsie Campbell: Yeah, my relationship with my co-founder was absolutely a love story. From the moment I met him, I just knew there was something different about our relationship. I was working at this early-stage tech company— I’ve been there about six months— and we were looking to add a designer to the marketing team. He walked in the door and we just clicked. I remember grabbing him on the first day to go get a cup of coffee and walking back and thinking to myself, “This guy is going to be an important part of my life and I don’t know what that means.”
Then we started working together and every day was so much fun. I think as we were in that environment— we started sharing stories, we started to understand where the two of us had come from, we had a lot in common— and there was a similar drive and passion and there was something about that friendship that it transitioned really well into a cofounder relationship.
Benji Block: What transitioned over time, because there were some hard moments there. What contributed to some of the difficulty and maybe what are some downsides that people don’t anticipate or expect when starting something with someone else?
Lynsie Campbell: For me, I think one of the issues that I didn’t recognize— and it really wasn’t an issue until it was— is that there was a 10-year age difference between the two of us. When I met Josh, I was 27, 28. We were hanging out in the office together, I said to him at one point, “Hey, we should grab a drink after work and talk about this idea we have.”
He’s like, “I can’t.” [I’m] like, “Why, what do you have going on?” He’s like, “I’m 18” and I was like, “What?” I’ve been working with him for a handful of weeks and didn’t even realize he was that much younger than me. He was very wise, very smart, he had started and sold a company before he was even 18 years old. He really was kind of a born entrepreneur. Yeah, I just knew.
Benji Block: As far as your journey, one of the things you speak to in the book is this idea of imposter syndrome and it’s been part of your journey. How have you intentionally worked to overcome that? Especially in the hyper-masculine tech startup world?
Lynsie Campbell: You know, it’s something that I still struggle with. I don’t know if that’s something that I’ll ever be able to shake. I work on it really hard but one of the things that I did and I’ve done a lot throughout my career— as you know, I mask those insecurities with humor and I try to make light of most situations where I’m uncomfortable. I gamify the experience so that it doesn’t feel so painful when I walk into a networking event of a hundred people and 80 to 85 people there are men.
It’s overwhelming and it is challenging that I’ve always tried to make it more fun and really find a way to enjoy it on the way.
Benji Block: Lynsie, uncertainty, and failure are absolute givens when you’re starting something from scratch and many with good ideas might shy away because of that. Can you give me an example of a failure or a moment you thought you may not be able to overcome?
Lynsie Campbell: I think one of the things that I’ve struggled with the most, and even looking back and writing this, the biggest mistake and the biggest failure that I made was choosing the wrong investors to join us along our journey to build our first company.
The effects that that had— it’s a snowball effect and if I could go back and change anything… I wish I would have, number one, vetted my investors like I did my early team members. I should have taken the approach of these are people who I want to be sitting at the table with me, [who] I want to go on this journey with me but when you’re a founder early, you’ll take the check because you just want to make your thing happen and I should have trusted my gut.
There was something telling me at this stage of the journey with this particular investor that I shouldn’t do it and I didn’t trust my gut. It had a real long-term impact, not just on my business but on my career overall.
Benji Block: How would you say, going off of what you just said about your gut, how have you learned to trust your gut as an entrepreneur over time?
Lynsie Campbell: Yeah, I know I really lean heavy into marketing sales biz dev. I am a creative at heart. I am somebody who walks the line between creative and analytical. I have struggled sometimes with I want to trust my gut— but what are the numbers saying? Or I want to trust my gut but you know, according to this historically I should go this route. If I have learned anything it is just to trust my gut. Ultimately there is a reason why you are telling yourself why the flags are being raised and you need to take a hard look at what that is.
Facing Your Fear and Choosing Happiness Over Heartache
Benji Block: For those that are listening to this and they are a bit afraid to start or they’re overwhelmed a little bit with the uncertainty of fear or failure, what would you say to someone that is in that space today?
Lynsie Campbell: This one took me a long time to learn, and I kind of remember the moment it hit me but, it is my mantra now and it is happiness over heartache. As you are going through this and as you’re hitting these pivotal moments in your journey, you have to focus on your happiness. You have to make sure that you are in a good place to be a good leader, to be a good friend, to be a good partner. If you are not taking care of yourself, you are not taking care of your business and I didn’t learn that early enough.
Benji Block: That’s so good. I want to stick with the harder parts of your story for a second because I have to say this, as I’m reading your book, your level of transparency is so amazing to read and I think it’s so helpful. Your cofounder walks away from ShowClix and there is so much to this story but several pieces seem to collapse at once, professionally and personally, and it leaves you burnt out. Chapter 11, you call it “taking a fucking break” and there are those listening that are in that space. Talk a bit about what led to that feeling of burnout and how you began to sort of try to deal with that.
Lynsie Campbell: Yeah, I had been running so hard with ShowClix in the beginning. I mean, I went five years without taking a vacation. I do not recommend that but I am a workaholic at heart. I am. It is who I am and going down that path and getting to the point where I knew I was burned out, I think it was partially mental and emotional. I just knew I couldn’t do it anymore and there is a moment in the book where I thought there was a light at the end of the tunnel and I was running so hard toward it and I got there and it just became darkness.
At that point, I had to take a break. There was no way forward for me. I moved to San Francisco and I ended up spending a year walking dogs on the beach and just really finding myself again, reflecting on the reasons why I had become an entrepreneur in the first place and what it is that I loved about it. It also gave me an opportunity to prove myself again because I have been living in the shadow of a lot of big personalities and big egos at ShowClix. I [had] kind of forgot what my worth was along the way.
I had to take a step back and prove to myself that I was who I was and I was capable and I could move forward and do this again.
Benji Block: Sometimes we don’t want to take a break but life just kind of says, “No, you are taking a break” right?
Lynsie Campbell: It forces you to, absolutely. I’ve been taking those hints a little bit better. I’ve been much more aware of what my body is telling me as I’ve gotten older and gone through these experiences honestly.
Benji Block: So then you’d take that year and then LaneSpotter, a non-technical solo female founder. What changes in your mind or how do you approach that differently?
Lynsie Campbell: You know leaving ShowClix and then walking away from that, I didn’t necessarily want to do that and I think that’s what makes it really hard. I loved what I was doing then getting to the point where I felt better— I could move back to Pittsburg and I came up with this idea for LaneSpotter— I did go into as a solo founder and I think for a couple of reasons. One, it started out as just a thing. It was like, you know what? Does this exist?
I am just going to do a little research. This has to be a thing, right? Just started poking around, and then that poking around turned into market research, and then the market research turns into feature outlines, and next thing you know, I’m building wireframes. My friends always joke the majority of my life is it’s like a bit gone too far. I just take a bit and then it just goes too far. It’s like I get a bike for commuting and then I start a bike company, but for me, that’s what it is.
Where it’s like I start to dig these little holes and I dig a little bit deeper and a little bit deeper and again with LaneSpotter too, it was very mission-driven. It was a big part of my life. I ride my bike everywhere so this was very much I was solving a problem for myself. I also didn’t trust anyone. I was not yet recovered from my first experience and I actually don’t know if I could have let a cofounder in at that time. I don’t know if I could have trusted somebody with that kind of relationship again, so I went at it as a solo founder.
Benji Block: That’s great and interesting because it is a change from that first experience. We talk a lot about how this second company, LaneSpotter was kind of you following curiosity. Do you feel like that’s something that can be taught or is it something that you’ve just had your whole life? What would you say when it comes to following curiosity?
Lynsie Campbell: I think it is just who I am. It’s always been who I am. I am constantly in some sort of research rabbit hole. I think it is one of the things I love about the marketing side of business too, it changes so fast and there are so many things to learn constantly so I can’t sit back and not educate myself. I am a naturally curious person, my degree is actually in journalism. I loved telling stories, I love digging for the details.
Yeah, with that being said, I think you can teach it. When somebody is passionate about something— I think that’s the other part of this too— is LaneSpotter, my level of passion for what I was building was so high that I wasn’t able to stop researching it. It was just the curiosity level was off the charts. I think too, if you are not born with that but you are working on the thing that you are really passionate about, you can hone those skills.
I think a lot of it is just about looking for the things that you don’t necessarily see on the surface. You know it is those gems that make all the difference.
Benji Block: Yeah, continuing to ask questions.
Lynsie Campbell: Then listening when people actually answer.
Benji Block: Yep, active listening leads to the next question, right?
Lynsie Campbell: Yes.
Benji Block: That’s great. Well, Lynsie, we’re going to start wrapping up our time together but when someone picks up a copy of This Better Work and they read it front to back, what do you hope they feel when they’re done? What do you hope maybe some of the main takeaways are?
Lynsie Campbell: I think some of the main takeaways, number one is that— we mentioned this earlier— you know failure is unavoidable in this situation. It’s what you do with those experiences that matter the most. I kind of joke that I brought this up before, before the interview, but I broke my wrist last week or I fractured my wrist and I went back to the doctor today and I am healed because I am Wolverine. But I think that’s a founder trait, right?
Being able to bounce back from something as quickly as you can and move on is a trait that you need to like. If you don’t have it when you become a founder then you need to hone [it] because things are just changing constantly. Another one is startups are really hard but people are actually harder. You know, we are saying the relationships with my cofounder and my team members and investors and the Pittsburg start community overall, those are some of the hardest things to manage actually during my journey.
The other one is that 90% of startups fail. We just don’t talk about that enough and what your idea of success might be when you start might not be what your idea of success is at the end of this thing. I know for myself that is absolutely the fact. We open to changing and adapting as you go through this journey.
Benji Block: For those wanting to connect with you further maybe online or reach out, what’s the best way for someone to contact you, Lynsie?
Lynsie Campbell: You can visit my website, which is www.lynsiecampbell.com. Unfortunately, my mom spelled my first name Lynsie and my joke there is it was the 70s. I don’t know what she was doing but she got real creative with it, so it’s lynsiecampbell.com. But yeah, feel free to reach out to me and I’m on Twitter, just Lynsie. I am pretty active there so you know, feel free to connect online. I love meeting founders, I love talking to entrepreneurs and I think at this point, it really is my calling.
Benji Block: That’s great. Well, I want to say congratulations on the book. I so appreciate the authenticity and the stories you share. Everyone should go pick it up and thanks for spending some time with us on Author Hour today.
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