Founder Growing Pains | Episode 5

“My fear as a founder is probably that I'm not afraid of enough.”

Entrepreneurs don't just achieve success with a snap of their fingers. For every successful business that is launched, there is a complex history filled with hours of work, struggle, and dedication—or what some would call growing pains. 

This is the Lunar Startups podcast and I'm your host, Twila Dang. 

The entrepreneurs of cohort one have definitely had their fair share of them—growing pains. Lunar Startups’ director of Lunar Services—now called Lunar Everywhere—Amanda Heyman explains. 

Heyman: I think the cohort members are facing what every startup is facing—resource scarcity, discomfort doing new things, having to wear all the hats when you don't have expertise in all of the areas...and so I'm not sure it's that much different than what most startup founders face and I think that it's great that they can be here, especially for a 12-month period of time and get that support throughout the year while they're working in their business and on their business. But it's hard out there. No matter what, it really is. 

One of the most complicated aspects of starting a business is how much knowledge you have as you begin your journey. Some entrepreneurs take a leap and figure things out as they go. 

This is Margi Scott from Take 12. 

Scott: So my startup, Take 12, is all about helping to provide solutions and support around the unpaid leave crisis in the US right now. Primarily, we offer crowdfunding services that allow friends and family to give financial gifts that equate to more time at home with baby in lieu of a traditional baby registry.

Margi started her company with a passion to help other parents and an idea.

Scott: You know, I think part of the only reason Take 12 exists today is because I just went for it. So maybe there were some things at the beginning and along the way that ‘Oh if I would have taken the time to get the answers I needed to feel comfortable taking the next step, I may not have taken it’.

While others start out with a road map based on previous experience, this is Muhammad Abdurrahman and Aaron Free from ClutchSOS.

Free: There's a really good book called Lost and Found here that I read after coming into the company and I went back on that and I realized like ‘Wow, yeah, there's a ton of things that I wish I’d known about this’. 

Abdurrahman: He came back, so I had explained to him. Yeah, I think I’d drawn that picture of the roller coaster kind of ride that would be on and where we were on it. One of the fun things about my work with with Aaron is, you know—this is, kind of, his longest journey in entrepreneurship so far. And so, I was showing him like, this is where we are and this is what's ahead of us and he's like, ‘Whoa wait, you mean, you know that things are going to go up and down like that?’ Yeah. He's like ‘Ohhh’. 

Free: It’s way more difficult than you can probably imagine. 

Abdurrahman: It’s one of those things where you can observe it. You can read about it. But unless you do it, it's not the same. Even if you read a book and it says ‘This is what it's going to be like’, that's not the same right as experiencing it.

 As the cohort worked day-to-day to build their companies, Lunar plays an important role in keeping them on the right track. Lunar team members like Amanda bring direct experience of entrepreneurship—often providing the cohort with insights that can only come from living and working through it. 

Heyman: I'd say my status as having run my own business and run a venture scale business absolutely helps me identify. I can give you an example today. I had on my calendar that I needed to pay estimated taxes for 2018 today. And so I was able to put that out on Slack which is not a sexy thing. But it's something that I'm living alongside the cohort as well.

Among the many challenges startup founders face, finding and building the right team can be very difficult. When you run a company whose daily work revolves around safety and the prevention of sexual assault like ClutchSOS, you have to be extremely extremely sensitive to how you recruit and build your workforce.

Muhammad from ClutchSOS explains more. 

Abdurrahman: I guess what I'd say is the biggest challenge in starting this company was the team…and remains the team. In this company, we’re so intentional about who we bring on that like...it's really critical that anybody who joins our team has empathy for the people who we’re affecting. Generally, I think we attract folks like that. But that alone is not the only qualifier, but it's just the first one. And that's a really hard thing to come to because I've met a lot of talented people who I would love to work with in any other capacity, but It wouldn't necessarily be a great fit here.

Adam from ClutchSOS shared how Lunar Startups has been a support in helping them with their process.

Free: I think finding the right people that, I mean, I think finding great people...is hard on its own. But then having this other layer of, you know, we take what we do really seriously. Not that other people don't, but we know the care that needs to go into what we're doing. That's another great thing about Lunar, actually, is that it helps us with those challenges. Because a lot of the people that are a part of this incubator really do understand that kind of notion.

While building a team can be difficult, most entrepreneurs will tell you that their biggest challenges in building a company are time and money—finding the resources needed to run and grow a business, plus maintaining a schedule that allows you to execute your vision can be daunting.

Margi from Take 12 found these challenges to be fun.

Scott: The biggest challenge in starting my own company has certainly been time and money—those two resources. But that's also, I guess, what has made it fun because it's just this huge puzzle to figure out, you know. I have joked for a very long time now that Take 12 is my night job; and it truly is. Because I have a lot of things going on. but it's so important to me and it's where my passion is. So it also makes it easier for me to find the time. I think also one of the biggest challenges is listening to everyone else about what the start of journey—what entrepreneurship should look like. I think there are several narratives in the world of, you know, well ‘If you're a startup founder, you're working 24 hours a day and, you know, there's never enough time and you have to be constantly working’. There's a lot of truth to that but there's also a lot of time and little corners of our days that we can...find to do the work that is meaningful to us. And so, you know, if I would have listened to that—and there were certainly times where I compared myself to other founders who were able to dedicate more time to their business—if that's where I had compared myself and said, you know, am I able to really do this? I would have felt that I should just give up. Because on paper, I don’t have the time to do this. But it also fuels me for the other areas of my life where I really need to show up.

The founders of ClutchSOS placed an emphasis on individual and team energy and how you use it. 

Abdurrahman: I think it's hard a lot of times, you know, going back yet knowing where to focus your time. I think that's the biggest actually hurdle I've had in the last year or so doing this...is like definitely things that took too much time into and too much energy into...that if we maybe we didn't do that, things could have been a little different. So yeah. 

Free: And I'd say focusing energy. So, I mean—I think time focus is really important; but also energy focus. I don't mean energy in some kind of—not to dump on the new agey people—I don't mean that at all. But I mean like, you know where you're putting your mental energy. Am I thinking about this issue? Am I thinking about that issue? You know, one of the biggest breakthroughs for our company was starting to think about some potential customers that we hadn't really considered before. Because of the discovery process, we found out ‘Oh this problem exists for this group of people and that group of people and the next group of people’. And before we knew it, we were like ‘Okay, wait a minute—we could super-segment all of these but actually there's so much learning we can gather that will help everyone if we don't at least in certain aspects. 

Abdurrahman: Yeah, and I think in product building too. There’s a lot of different ways you can go about that.

Free: So many.

With so many details to track with a new business, it can become overwhelming. Adam from ClutchSOS relies on focus to help him stay the course. Adam really believes that focus is not just about how you use your time, but how you hone your concept.

Free: I've had some entrepreneurial dreams before but this is the farthest I've gone in entrepreneurship so far. Sometimes you just don't know how difficult it's going to be or what things to focus on. I think focus is super key to things—to figuring out. I think you want to...know different possible paths and you want to figure things out but talking with people and really understanding—knowing what what your niche is and what you're really doing and going after that—I think that's very important. 

Music plays. 

We'll be right back after the break. 

Welcome back to the Lunar Startups Podcast. 

We talked a lot about what our entrepreneurs didn't know going into the start of their businesses. Some welcomed the unpredictable nature—others did not. But all agreed that there were things they wish they had known at the beginning. Margi from Take 12 was philosophical. 

Scott: What do I wish I knew when I started my company? Probably that it was going to take a lot longer, and by “it” I mean everything—every step that you think is a no-brainer takes so much longer than actually makes sense in your mind. That said, I'm really glad I didn't know anything because it might have prevented me from taking a lot of those next steps.

Muhammed from ClutchSOS was a bit sarcastic.

Abdurrahman: And I wish I'd known how much money was going to take. I know it was going to take way more money...but I wish I'd known that. I wish I'd known how much energy, time, and focus it was going to take and I wish I had known—you know what? wishing is for suckers. Honestly, I mean...not to quote Ice Cube.

Free: Sucker free.

Abdurrahman: Sucker free. This is a sucker free podcast (laughs). But you know, wish? I don't know man.

As Lunar’s Managing Director, Danielle, explains...these growing pains extended to Lunar too.

Steer: How do we take best practices from accelerators and incubators that are working for a broader audience and redesign those things that aren't working? So we really needed to be intentional and iterative and thoughtful and inclusive in terms of our question and our questions that were asking the cohorts and that were asking ourselves around creating the program; in terms of who our vendors are, who our workshop leaders are—all of those components. So, it's been a really exciting few months, but there's definitely been some highs and lows because you learn fast and have to pivot in some ways. I think we also, as anybody, set expectations for ourselves and when you come in at different direction—even if you're exceeding expectations based on how they might change—because you didn't meet that initial goal, there's a little bit of reframing that needs to happen to go ‘No, that's okay, we moved intentionally away from that because it wasn't serving our community’. Now, we're going in this new direction. We have new metrics. We have new success meters that we’re looking at. Remembering to be on that new track is a surprising challenge that I've been thinking about these past couple of weeks.

Amanda Heyman, Director of Lunar Services—now called Lunar Everywhere—thinks it's important to remember where you started so you'll know where you're going. 

Heyman: It's good to be on a new track and it's good to be okay with pivoting, but I think it's also good to go back to wherever—you know, have some way to look back at where you were three months ago so that it's not constant goalpost shifting. I know I have a tendency to constantly move my goalpost bigger and bigger and bigger and then you feel like you're never getting anywhere. So I think it's good to do both—to make sure that you realize where you started from and how much progress you've actually made instead of just saying ‘Oh, well, I haven't done the big 10x, 50x, 100x dream yet and it's only four months in, what is wrong with me?’

For Lunar Startups’ Program Director, Jeffrey Aguy, the challenge was more personal. Adjusting from the independence of business leadership to being a team member in a facilitator’s part of a unit. 

Aguy: I think my greatest challenge has been acclimating myself to a different culture than most organizations that have been part of. I've been an entrepreneur my entire life. I've owned my own company since I was twenty-one and even now I still have companies that I own and I think my biggest challenge has been fitting into a leadership structure where I'm not the one that's necessarily leading. But even in that, it's been a smooth transition. Danielle does a great job of empowering me to lead. I just lead differently. So I think that's been the biggest challenge—really adapting.

Is fearlessness a growing pain? Most would say it is a driving force for many entrepreneurs, but others also see the potential pitfalls on the road to success. 

Back to Margi from Take 12. 

Scott: My fear as a founder is probably that I'm not afraid of enough. Every once in a while, I just have this moment where am I completely insane for ever attempting to do any of this so I try to check myself and actually develop some healthy fears. I think the reason I'm at this point is that I just ignored fear. Truthfully financing, you know, I think just being able to continue to operate and grow to the point where I'll be able to sustain, you know, being in this early phase and being in the world of fundraising has certainly taken longer than I ever could have forcasted. So I think, you know, my fear...I guess is that I'll just be able to meet all of the expectations that I've set for myself and ultimately to make this thing, you know, a raging success.

Lunar’s fearlessness in working with the diverse population of founders sometimes runs counter to old external narratives and perceptions of what the cohort members are truly capable of accomplishing. 

Steer: One of the biggest challenges that we face right now is there's this kind of internal tension that we feel around—we are helping high potential, high growth entrepreneurs—and because they happen to be women and people of color, many external organizations or investors or large institutions see us as a charity case. 

They see us as a place where we are helping people who are underrepresented or minorities. They have all these labels for us. These are just great entrepreneurs that we want to highlight because they are serving a broader market. And so that duality of ‘How do we elevate their stories and their uniqueness and honor the different perspectives that they bring to the table without devaluing that aspect of who they are?’ It is a huge challenge for us when we're talking to sponsors and funders and even potential consumers that we try to connect our startups with. 

We want to enable our entrepreneurs to bring their full selves to the table in a system that is constructed in a way that doesn't necessarily allow that. So how do we change the system to allow for people to show up as their full selves while also trying to work inside of it when it doesn't allow for that?

Even with her previous experience combined with community support, Danielle recognizes that Lunar Startups still faces some uphill battles. 

Steer: That might feel a little bit redundant. And I can try and say in a different way but I think that duality of supporting people who are historically excluded or marginalized in a system while still trying to prove that they are just as valuable is something that I didn't necessarily expect and yet, I can't say I'm not surprised having been in non-profit work for a long time.

An important growth lesson for Lunar Startups came from their understanding that cultivating relationships and working together to build community had to start at the most basic level. First, they had to listen. 

Steer: We are listening as an organization. We are listening to our customers. We are listening to the startups. We are listening to the community members and not projecting our own solutions onto them. We are working to help them be their most full, authentic selves at every table they get to sit at. And also trying to inform the broader ecosystem about how others can make the table bigger and invite people to be fully authentic and present and themselves. We all have different ways of being and we need to make space for that. It's really, really, really hard work. The more privileged you have, the harder you have to work at uncovering your unconscious bias or how you're benefiting from that privilege. So it's important for us to lead by example—to make way and space for that type of really challenging discourse so that people can be safe in the environments in which we're working. Sometimes that means I step out of the room, to be honest, because I shouldn't be there and because I can't relate and I'm really okay with that.

Being able to be open and honest about your experiences and struggles as a founder flies in the face of traditional incubators. At Lunar Startups, it's not only encouraged—t's celebrated.

Steer: Founders are able to come in and be safe and say ‘Today is not a good day for whatever reason’. It doesn't, you know, have to be unfortunate circumstances. It could be, you know, their kid is sick or maybe they had a good win and they're not quite sure how to process it or they had bad publicity or whatever else it might mean. But needing to make sure that we are taking care of the whole human at every point...of the organization's development is a really important component of what we're trying to do. 

Right now, authenticity is one of those buzzy words that doesn't necessarily mean a lot of things to a lot of people—it's kind of like synergy was once upon a time. But when we talk about a person being able to bring their authentic self to the table, it's really about the space that we're creating so that they can feel safe—so that they can feel well supported. Whether it's that their kid is super sick and they don't have daycare or they have a family member who passed away or some kind of tragedy or they have a big win and they don't know who to call or they don't want to, you know, sound the alarm and tell everybody and feel braggadocious. We can be that community where they get to come in and say ‘I did this thing. I checked a box. I made a win. It was small. It was large. I had a failure—a lesson learned. I'm not okay. I am okay’. All of those parts of the entrepreneurial experience are very real and oftentimes they either trend high or trend low. 

There's this roller coaster of experience. Being an entrepreneur is one of the most challenging things that you can choose to do in this world and having a safe community where you can come and be at both ends of that extreme is a really important aspect that not only changes the perspective of getting away from this heroic entrepreneur archetype that is highly effective and highly efficient and you know coding 18 hours a day and looks a certain way to we have a mom with four kids—with a full-time job—who has a startup and is killing it. How many times do you get to hear that narrative? 

It's not often talked about, so when she comes in and says ‘My twins are really, really sick. I haven't slept in four days, but I just got a check for $100,000 from [my] first investor’, we get to celebrate both sides of that. That's a really important aspect of the environment and culture we're trying to create.

Ultimately when it comes to entrepreneurship challenges are ever present, but they serve a purpose. They are a vehicle for growth and growth is a necessity for startups to survive. But growing can be scary and having a safe place to work through it all, can truly make a difference.

Lunar’s Jeffrey Aguy sums it up best. 

Aguy: There are so many things that I could be appreciative for the culture of our team. 

The respect that we have amongst each other and our skill set and so many others, but I think and I know what I appreciate the most is the belief that we could truly challenge each other to grow...and do it in such a way that is safe—challenge each other in a way that is safe. But definitely without challenge, there is a grill. So what I appreciate the most is the team's ability to help each individual grow and become much better than they could have been or that they have been themselves prior to working at over. 

Thank you for listening to this podcast. 

If you'd like to learn more about Lunar Startups or apply for an upcoming cohort, check out the website at lunarstartups.org. 

We'd like to extend a special thank you to the Glen Nelson Center at American Public Media, Knight Foundation, and Osborn370 for their continued support of Lunar Startups.

This podcast is a Matriarch Digital Media production. Executive Producers: Twila Dang, Brittany Arneson, and Josette Elieff.