Sleepless Nights on the Lower Eastside of Manhattan:

An Interview with Rachel Renock

Note: This blog is a bit longer than our usual but Rachel Renock was so damn articulate that we had to run with the whole shebang, pretty much uncut!

“I think for my own mental health, reigning in my inner voice and that constant dialogue is critical,” explained Rachel Renock, the 27-year old co-founder and CEO of Wethos, a tech company on the Lower Eastside of Manhattan. That running dialogue makes sleep very difficult and beats her up mentally, but has also driven early successes that includes attracting $1 million in VC money. Of course that success brings more pressure to execute and close on the next round of money. It’s definitely the classic entrepreneur story that involves Red Bulls at dinner and working into the early morning hours – only you’ll discover that Renock brings a real honest and refreshing voice to the mental health quotient as she strives to avoid “breaking” herself and the company’s burgeoning team of ten.

Some quick backstory for context. After graduating from Syracuse University in 2013 with a degree in Design and Visual Communications, Renock worked in the advertising world, both as a freelancer and a company employee. While serving as an art director for Havas Worldwide, she was freelancing on the side in the Spring of 2016 for a couple of LGBT nonprofits in New York City. Part of the LGBT community herself and focused on that area, she had nonprofits asking her if she knew any web developers, graphic designers, and grant writers. “They didn’t have a great place to get contract based resources. And on the other side I couldn’t believe that I couldn’t find work that aligned with my values. So that’s how the idea for Wethos was born.” Renock quit her advertising job in August 2016 to follow her passion and launch Wethos, which matches nonprofits with affordable freelancers who “care about” their cause. She also on boarded two equally driven co-founders. “We wanted to connect people with more meaningful work, and we were going to add purpose to the workflow,” she recalled. The company takes a 15% cut of what is billed.

Preparing to Jump Off the Cliff (and Bartending)
Quitting a safe company job just a few years out of school in pricey New York City to launch a business had its risks, so we had to ask Renock just what was going through her head in making the decision. She began her answer by saying she absolutely subscribes to LinkedIn founder Reid Hoffman’s oft-quoted view: “An entrepreneur is someone who will jump off a cliff and assemble an airplane on the way down.” It is a metaphor that has stuck with her. Renock went on to explain, “As we were preparing to jump off the cliff, we were gathering all the parts.” Everything was calculated, including a time-frame in which to make the business viable or pull the plug.

“In making the decision to quit,” she said, “from a practical perspective, do we have enough money to stay alive; is there a time period where we need to hit a certain goal, to accomplish something, to prove this is viable. For us it was six months. That was how much money I had in my bank account. I had six months worth of rent. For me, I said, if I can prove this is a viable idea within six months, I will figure out a way to keep it going. We did end up bartending, working in coffee shops, freelancing to keep the lights on for that full year before we were able to raise some money.”

While there were many unknowns, Renock did know she had to give it a shot: “From a more emotional aspect of it, I’ve always been in the camp that I at least have to try. For us, the opportunity we had discovered in this big white space was too good to not at least try.” Before jumping off the cliff, they gathered as many parts as possible, made as much preparation as possible, which was key.

A Brave New World & Picking Co-founders
Yeah, we’re squeezing in an Aldous Huxley allusion, but why not, especially when the tech world is involved. Mind you this isn’t a futuristic dystopian story, the opposite actually. Anyway, Renock acknowledged, “It was absolutely new. When we entered tech, we didn’t know a soul. I didn’t know the difference between an angel investor and a VC when I quit my job.” Even so, entrepreneurship lurked in her DNA – her mom had started a few businesses “in her past life” with varying degrees of success and failure. “My parents very thoroughly warned me this is a very emotional rollercoaster. It can affect your personal life. It can affect your mental health, obviously your financial stability and all of the things that go along with it.”

Through the “emotional rollercoaster” Renock’s choice of co-founders has been a key source of strength and stability. However, from a more practical standpoint, there’s also the pros and cons of having heterogeneous versus homogenous co-founders to consider, which we asked Renock about. How did she pick them?

“I reached out to them because in my experience they were extremely smart, motivated, productive people that in our industry were being widely overlooked and underutilized,” she explained. She had worked with them on a couple of accounts over the course of a year, therefore she felt comfortable that she knew what they brought to the table; namely, shared passion for the business concept and the right personalities. “They definitely had strengths in areas that I had weaknesses, but that manifested itself after the decision was made. I tend to be a little more Type B, kind of creative, pie in the sky, and they kind of bring me back down to earth, and move the business forward on the day to day, and they are more detail oriented and process oriented, so they help balance me out in that way. But at the time I was making the decision, it was more about who are the people who will align with this idea, who will be into this, and they had always been socially active people. On top of that, they had personalities that I wanted to work with.”

Renock emphasized how in her opinion these smart, driven women “were super underutilized” and how she “hoped if I gave them an outlet they’d come about, and they absolutely stepped up, and that’s what got us here.”

Getting back briefly to how they got here: A month before the 2016 presidential election they launched a beta; after the election of Trump, the Wethos team saw “a huge spike in activism, a huge spike in people who wanted to do something, to give back, to create a better world, things of that nature.” Translation: in the subsequent six months, Wethos acquired about 200 nonprofit organizations and a thousand freelancers. “And with that we were able to raise our first round of VC,” concluded Renock. “Now we’re a humble little team of 10 on the Lower Eastside of Manhattan, focused on creating the right product.”

Money and Co-founder Dynamics
With just under a year having passed since they quit their jobs, the injection of capital was certainly validation they were on to something. But along with the VC money comes additional responsibilities and pressures. And we know that money can impact relationships, so we asked Renock if the dynamics of the co-founder relationships had changed. Was all copasetic? “The dynamic has definitely shifted,” she answered. “Everyone sort of came to the realization of the gravity of the situation, the fact that the stakes are higher.” She further explained, “The dynamics kind of shifted from three people on a couch doing everything evenly to me really having to step up, and be the CEO, and talk to the investors and go to the board meetings, and do the press releases, and do all the things that create a hierarchy that maybe wasn’t as strong as it was before, even though I was always the quote unquote CEO.”

Although the final decisions often fall on Renock, her relationship with her co-founders remains strong and mutually dependent. It’s all about open, honest communication: “I think for us I just continue to check in with them, have one-on-ones, have very candid conversations when things are working or not working, and I think that keeps us sort of sane. We’re always very honest with each other. We never let tension turn into resentment. And we always address things head on. So, it’s knowing when to give people space and knowing when we have to sit down and have a tough conversation. We rarely just bury stuff and walk away. It’s just not our style, and I think that’s been really helpful in this tough transition period.”

Isolation Is a Factor, Especially in Tech
So we’ve talked to a bunch of entrepreneurs, and a number of them have raised the issue of feeling isolated. This is interesting because it’s somewhat counter intuitive in that typically entrepreneurs are social creatures with decent networks (see our interview with Dr. Michael Freeman). Take Renock. By all accounts she’s involved, has a network, seems to have a good relationship with her parents, but has and still feels a certain alienation at times.

To begin, she had no friends who had taken the entrepreneurial plunge – they were all still in advertising. “So it did become a bit alienating,” she explained, “and it was hard to vent or have conversations with my friends because they weren’t anywhere close to doing what we were doing. It was hard to empathize with what was going on with us, so I definitely leaned on my co-founders more in that sense. And it was definitely isolating to not be aware of anyone else who was in the same position as we were.”

We asked her if now that she’s been at it for a year and a half, does she have a broader circle to lean on? “I definitely do to a certain extent,” she answered. “But I think a reason that this topic that you’re talking about is so important as it pertains to tech is that it’s very difficult to get tech people to admit when things aren’t good. Most founders or investors don’t want anyone else knowing that actually behind the smoke screen it’s a shit show. In tech you’re constantly encouraged to paint a picture of success and positivity. There’s this whole mechanism that teaches people that things are an overnight success. Like Snapchat was an overnight success. Like Facebook was an overnight success. And nobody wants to talk too much about the challenges because you don’t want to scare off potential investors, or potential employees, and so on and so forth.

“So there ends up being this culture of silence when it comes to challenges that’s just starting to open up now. We’ve tried really hard to blog about all of our our challenges, and it’s always just risky because you never know when the next investor is going to come along and say, You know I read a blog post you wrote three months ago about your internal processes being a shit show so why would I invest in this company? So you’re kind of encouraged to paint a positive view of whatever you’re doing. Even with the circle of people who maybe understand more, finding people who will actually admit there are challenges that they are facing, it can be hard and it can take time.”

Why Is Tech Different?
We’ve talked to entrepreneurs who are into clothing, retail, healthcare, among other non-tech businesses, and they too have similar mental health challenges, so we wanted to know from Renock why she differentiates tech? Why is it more intense?

Without missing a beat, she said, “Because I think the way tech is currently set up, there’s a lot of ego for lack of a better word, and there’s a lot of people in tech who encourage this quote unquote hustler sort of mentality, which then leads to this unhealthy work-life balance, which leads people to totally burn themselves out. And tech is founded on this idea, move fast and break things; and I say this all the time, when you move too fast and break things, you end up breaking people (our italics). I think tech is at this reckoning point with that in particular. If you’re working 80 to 100 hours a week and your draining your development team and you’re draining your sales team, and everyone is miserable so that you can accelerate your growth, you end up breaking people and that causes a lot of mental health problems. I think because tech is very much like move fast, grow quickly, hit the ground running, make mistakes, break things, it’s like all this sort of very aggressive … There’s a lot of aggressive connotations that comes out of it. It causes people to wear themselves very thin, and end up having breakdowns.”

Put a Stake in the Ground
Her viewpoint begs the question of what her own personal experience has been; and now that they have a team of ten, what are they doing to encourage a healthy work environment while striving to build the business with a VC keeping tabs on them. Well, in those early, embryonic days – laying the groundwork for the business while still collecting a paycheck – Renock was the quintessential entrepreneur working until 2 a.m. “It was brutal,” she said bluntly. “I would walk home from my advertising job, and I remember stopping at a bodega and grabbing a Red Bull at 6 p.m. And then I would go to my apartment and build out another couple pages of the platform. We were pulling really late nights when we were employed by another company, which is another reason we decided to take the leap. It’s the classic, I can do two things poorly or one thing well, and if I have to choose, this is what I choose.” That first year was full throttle day, night, weekends. “The only time we would take breaks is when we were right at that tipping point of like, I’m gong to lose my mind if I don’t take a day off soon.”

As the journey unfolded, some semblance of balance was established but then different stressors came to the fore. “As we got more established and we hired more people we were able to off load some of that weight,” Renock said. “I think we established a much healthier work-life balance. We also had been validated which changes your mentality a little bit by raising the money. OK, we’re definitely onto something, so that’s not necessarily keeping me up at night, but how are we going to execute is what keeps us up at night now. So I think hiring a couple people and keeping in mind that those people have lives and mental health to take care of and we’re now responsible for people outside ourselves, we’re able to strike a better life-work balance currently than our first year.”

Policies were put in place. The company has set work hours. Team members can work from home. Meetings are only permitted on Tuesdays and Thursdays so they “can have deep work days” Monday, Wednesday, and Friday. Team members are not expected to be online after 8p.m. or on Sunday. Same if you’re sick or on vacation. Renock’s message: “Please take the time to rest. Regain your strength. Because burnout doesn’t affect just one person, it affects the entire team. If you don’t have the wherewithal or self-awareness to realize that I’m reaching that tipping point, then you’re going to affect everything that we’re doing.”

“It goes beyond just creating that culture, beyond just policy, but putting a stake in the ground. So I think it’s setting expectations and creating those boundaries” between work and home life. She worries about what work from home policies, flexible hours, and the gig economy is doing to us in terms of there being a lack of boundaries, or a breakdown of barriers between home life and work.

The Relationship Cost
It’s great that Wethos is putting policies in place and staking out boundaries; however, what about the mental toll on Renock? We wanted to know what she was doing personally to improve her work-life balance, including personal relationship issues. She was forthright about the challenges. “I struggle with turning my internal dialogue off more so than walking away from my devices,” she said. “I’m pretty hardcore attached to my phone and I’m always just thinking.” She knows she needs to reign in that inner voice and constant dialogue, which can be draining and make sleep elusive. She wakes up many times every night. Sleep was always a struggle but more so now with the added pressure of running an early stage start up.

Personal relationships? Not good. “In terms of my friendships and personal relationships, they absolutely have suffered,” Renock said. “I think in the first year of having a totally different schedule and totally different lifestyle honestly than the rest of my friends, caused me to be very distant. I was bad. And I had no money either, so it’s not like I could go out to brunch with everybody every weekend. Or I could take someone out to dinner. I was struggling to get by so that really restrained my ability to do anything. It caused me to sort of isolate myself from a lot of my friends.

“A drained bank account, drained emotional energy, and barely any time absolutely affected my relationships as well. I definitely neglected a lot of what I could do inside of those relationships, so in the end I decided it’s better for me to take some time alone and focus on what I’m doing and try not to stretch myself too thin.”

One of her New Year resolutions is to rebuild some of those friendships, to spend more time and energy on relationships. We asked her how she was going to follow through. “It’s a matter of being committed,” she said. For example, if she puts a business meeting on a calendar, she will be there. She doesn’t like shifting things around, being flaky. “I want to apply that to my personal life,” she said. “I want to make sure I’m prioritizing people in my life as much as I am the company, which is really, really hard because we’re at such an early stage and we have so much to do. But I don’t want to come out the other side of this with an IPO, for example, and have no one there to pop the champagne with because I totally ignored my entire personal life for five years. I think that would leave me very isolated and feeling alone. Don’t bail on plans. If you’re going to make a dinner date or drink date, show up. Even if you’re tired, even if you want to go home, just be as committed to that as you are to the company. I’m hoping that that small shift in and of itself will help.”

Imposter Syndrome and Reflection
We circled back to the different kinds of pressure she feels with a million bucks in VC money on the line and how she manages it. It’s a multi-pronged approach that relies on her co-founders, journaling, and therapy. “I struggle a lot, and still do, with imposter syndrome,” Renock explained. “I think that is one of the most challenging and damaging states of mind an entrepreneur can have. For the first two months after we closed on the money I was sort of in awe, I felt a little stunned still by the gravity of the situation. And there is a lot of added pressure. We do have goals we have to meet, we do have to get to the next round.

“There is additional pressure to support a team outside just of yourself and maybe your co-founders, so for me I try to lean on my co-founders as much as I can. I also write a lot. I just kind of journal a lot to get my thoughts down on paper. I go to therapy every other week. I’ve had times when my bank account is so empty and I scraped together the last amount of cash just to go to therapy again just to help with my mental health and my state of mind because it is a lot of pressure. It’s hard and I am fairly young. I write a lot down just to get it out. I had a rough day today so I’ll journal a little bit tonight.” The writing helps her put things in perspective. It’s about reflection. “Everything happens so fast and things change so quickly, we don’t even have time to really process it, so I think writing helps me process a lot.”

The Apocalypse and Measuring Success
It’s no secret that there are plenty of entrepreneurs who wake up at 4 a.m. fearing it will all go up in flames. It can bring on self-doubt and even paralysis, so how do you soldier through? For Renock, she’s clearly an incorrigible optimist. “I definitely have those moments; they’re not too often,” she said. “I tend to air on the side of optimism but I absolutely have those moments where you wake up at 4 in the morning thinking, Holy shit, we’re not moving fast enough, we’re not doing enough, we’re never going to get to the next round. And then you picture that playing out. What does my life look like when I’m writing a blog post about how we failed.

“The thing that really works to pull me out of that head space is to continue to tell myself what I told myself when I quit my job, which is all I have to do is try. If I do everything in my power to try to get this thing to work and I pour all of my energy into getting this thing off the ground and making it happen, then if it fails, at least we tried. That is the mentality I have to maintain to pull myself out of those moments. If it goes up in flames and you start poking holes, poking around, and having regrets, Oh we could have done it this way or we could have done it that way, I’m sure that would happen, but at least I gave it a shot. At least I tried to make something out of my life. I took a chance, I took a risk, and it worked for a second.

“To me, I’m in a position where we’re in an office, we’re able to hire people, and I’m able to pay my own paycheck, and I see that milestone as a success in and of itself. Success is a moving spectrum. Now success is slightly different, it’s getting to the next round, it’s getting to the next milestone. But we hit a milestone that I was just dreaming of for an entire year. I have to continue to remind myself of that. I’ve made so many incredible friends and connections in the tech space that if it did go under and I needed a job, I know I can leverage that network and people would reach out to me. So again, it’s all about trying for me, doing the best we can to get the thing going, and beyond that, it’s sort of out of my hands.”

Further Thoughts on Mental Health
“In terms of the mental health thing, for me, the biggest step that tech really needs to make is creating a safe environment for founders and entrepreneurs to speak candidly about their challenges. I think even investors too. I think investors feel the same kind of pressure to say my whole portfolio is doing amazing, it’s booming, and everything’s awesome, you should keep your eye on x,y,z company. And probably behind the scenes they’re constantly putting out fires. Everybody knows that.

“What I crave from the tech space is to admit that sometimes when we move too quickly, we break people. And that we need to be able to speak candidly with each other in order to move past some of these challenges and learn from each other. Because if no one talks about challenges, then you feel like you’re the only one struggling and then you feel incredibly isolated and alone when in reality many, many people dealt with it in the past or are currently dealing with the same problems. I’m looking for people to open about their challenges and not feel ashamed about them.”

A Reckoning Point
With some of the #MeToo spotlight on sexual harassment in the tech world, we had to ask Renock about that. An activist who is working to give women a stronger voice in the tech space, she spoke with clarity on the topic. “The empathy we’re starting to see in the space quite frankly comes from a lot more women entering it, and a lot more women talking to each other and able to open up and talk about challenges and kind of encouraging guys to do the same,” she explained. “Men are more apt to cover it all up and bury it, which is the tendency of the masculine point of view, whereas women are like, Let’s talk about the issues, and get it out on the table.

“Women have so many incredible natural strengths. They make unbelievably motivated employees. They’re so empathetic. They tend to put the team before themselves. They tend to see the bigger picture and put their egos aside and understand we need to do what’s best for what we’re doing and not what’s best for them. Having that diverse perspective at the table is really what creates innovation.

“For us, we feel like we’ve been left out of a lot of decisions. Women have been dealing with this for hundreds of years. All of our products have been made by men, designed by men, and sold to us by men. Now I think a lot of female entrepreneurs are stepping up and saying, Wait, we’re going to reinvent bras, and we’re going to reinvent tampons. We’re going to reinvent all of these things that were made for us in the past that we now have the power to do ourselves the way that we want it. And I think that’s really, really powerful, so I’m very optimistic. I think we’re in the midst of a huge culture shift that’s going to be good for everybody. I think more women entering the tech space is going to create an incredible environment for innovation, and I really do think we’re at a reckoning point.

“Men have a lot to learn from us. Now is the time to really do that. I hope people can open themselves up to that, and open themselves up to the possibility that maybe they don’t know everything, and that there’s a new way or different way of doing things. And it doesn’t have to be a dog-eat-dog world all the time, like maybe we can be more collaborative and less competitive. I think that’s going to create a better work environment for everyone moving forward.”