From military service, to a failed startup, to raising $20M for Ethena – this is my non-traditional path to techFeatured

I often talk with junior folks who are very concerned that if they somehow miss one rung on their career ladder, or they climb too slowly, they’ll fall to their professional death and never recover. While I understand where this fear comes from, my path has been anything but structured. I’ve wound my way through several industries before becoming the co-founder and CEO of Ethena, a Series A startup that’s reinventing compliance training.

A non-traditional path is an asset because your career progression isn’t a ladder, it’s a jungle gym. If you’re taking the generalist path, progress won’t be linear. That can feel stressful because you can feel “behind” your more specialized peers, or that you’re lost wandering in the woods.

But a generalist path can make you a great leader because you’ll know how to operate outside of your comfort zone and thrive in ambiguity. These skills are in high demand, especially in tech, where roles require people to grow really quickly. One day, you’re an individual contributor and weeks later, you have a team of 5.

Even if you’re on a more specialized path, flexing new muscles is incredibly important. It keeps you agile and dusts away mental cobwebs. Here are some of the things I took from each stop on my windy career path:

From the military: Leadership

I spent 7 years in the U.S. army, first as an engineer officer where I deployed to Afghanistan, and then in Civil Affairs, where I led training of foreign militaries in Cambodia and Mongolia.

I learned a lot in those years, but what I draw from most frequently is leadership 101. One of my favorite officers once told me that great leaders really just care (he said, “give a sh*t” but you get the idea). Great leaders care about those they have the privilege of leading. They think a lot about what their followers need, and they work hard to give them that. That’s not the same as wanting to be liked – being a great leader is more like being a great parent. It’s caring enough to say the hard thing or watch someone fail.

In doing something physically scary like jumping out of a plane or deploying to war, I also got to physically observe great leaders. The best ones projected calm especially when things got scary. Flailing your arms or raising your voice rarely help the situation. But a funny joke when things seem dark can really help keep everyone’s spirits up.

From a failed startup: start by starting

Toward the end of my time in the military, I found myself frustrated by bureaucracy. I wanted to work at a faster pace and with more autonomy. I also got really fixated on solving a problem I was facing – eating healthy with limited time. Together with a grad school friend of mine, we started a startup, Supper Meals, which aimed to connect local chefs with people looking for healthy, ready-to-eat meals. We bootstrapped the company and I learned what it takes to start a company from nothing.

I learned a lot in the year and a half that we worked on Supper, but I’ll skip ahead to the “failure” part because that taught me the most. My co-founder and I decided to wind down Supper and sell to a local company for a modest exit. But we gave our company a home and perhaps most important for me, I saw the lifecycle of starting a company and then winding it down. I realized that failure, while not ideal, isn’t actually death. It’s motivation to take what I learned, apply it, and win the next round.

I once heard an instructor in military survival school say that getting hit in the face is really helpful because you realize it’s not as painful as you think it’ll be. That’s what failing at my first startup felt like – I got hit in the face, and while I didn’t like it, it also wasn’t the end of the world.

From consulting: structure is helpful

After winding down Supper, I didn’t know what to do, so I talked with a bunch of smart people. They told me I should either join an early stage startup where my generalist skills would be useful or I should go into consulting and gain more private sector experience, until I figure out what I’m actually interested in.

I couldn’t find a startup I was passionate about so I did the default thing for “I don’t know what I want to do with my life” and became a consultant. I joined McKinsey where I stayed for a year. I’ll be honest– I did not love it. But I did learn.

But I am glad I did it for a few reasons:

  1. I broadened my network – this ended up being super helpful when I raised my first round of fundraising for Ethena. Previously, my network was mostly folks in the military and government, but at McKinsey, I met people who eventually became early angel investors.
  2. I got some of the business best practices juice in my system – it’s really helpful to know how large organizations work, even if, like me, you want to build a startup because the goal is eventually to scale it. At McKinsey, I learned a lot of management basics that I still draw on, things like how to structure meetings and how to use decks to tell stories. It’s not the sexiest stuff, but it’s incredibly helpful, especially as Ethena grows.

At Ethena: it’s all useful!

I’m now the CEO of a 50+ person company. We’ve raised over $20M in venture capital and we count companies like Netflix, Zendesk, Zoom and Carta as customers.

To be clear, none of my previous experiences “prepared” me for this. Everyday is different and my role is scaling as fast as the company is. But because I’ve had to grow and adapt in all of the different roles I’ve held, I’m pretty good at the act of figuring things out, which is basically what I do all day.

I’ve developed the skill set of figuring out what a role needs, figuring out what skills I currently have and which ones I need, and then figuring out how to get those skills.

iynna's profile thumbnail
Non-traditional is where it's at! Your background is so fascinating and I am so excited to see how you've applied each lesson learned along the way! We need to hear more stories like yours, especially from veterans who are often left out of the whole diversity equation.Cheers to your success and journey, it's only the start!
roxanne's profile thumbnail
Thanks for your kind words!
iynna's profile thumbnail
Also your background really reminded me of one of Bschool friends so I shared with him and tuns out you two worked together! It's David! He has spoken so so highly of you and did tell me that we should connect. I am so happy we did through Elpha :-)
roxanne's profile thumbnail
Such a small world! David is the best. So glad you're connected.
victoriamelnikova's profile thumbnail
I am super curious to hear all about how you transitioned from working at McKinsey to becoming a CEO of a startup? I am also doing to know about your first steps in the fundraising journey. Please tell us more!
roxanne's profile thumbnail
hi! re: transitioning from McKinsey to being the CEO of a startup, the jump was actually pretty easy because initially, I was the CEO of a 1 person startup :) The most important thing I did after that was find my incredibly co-founder, and then from there, we've grown our team to 50+ over the past 2 years. I suppose it's like that story about a frog slowly cooking in hot water-- the transition didn't feel so intense at first because I was leading a really small team, which isn't that different from what I did at McKinsey, and then the temperature has been consistently rising since then.re: fundraising, oh that's a longer answer! I recommend for first steps reading what YC puts out, since I think their stuff is very good, and then have conversations with other founders a few steps ahead of you. Don't talk to investors yet, since they aren't there to teach you, they're looking to invest, so there's no such thing as a casual, pick-your-brain convo between a founder and an investor, IMO.Hope that's a start!
victoriamelnikova's profile thumbnail
That's awesome, thank you!
BLACKAPPL's profile thumbnail
"...great leaders really just care (he said, “give a sh*t” but you get the idea).... That’s not the same as wanting to be liked – being a great leader is more like being a great parent. It’s caring enough to say the hard thing or watch someone fail." I cannot agree more. Asking myself whether I (still) CARE everyday and especially in situation when I feel "grey" about what I do has been transformational. It is the best guidance when interacting with people, who work for me. Thank you!
roxanne's profile thumbnail
Oh I'm so glad to hear that it resonated!
HHoang's profile thumbnail
Thanks for sharing @roxanne. Amazing jungle gym example and very inspiring!! I would love to hear more about how you managed to convince the investors after the failed startup . Did they drill on your 'execution capability'?
roxanne's profile thumbnail
Great question. Weirdly, early investors didn't ask me that much about my failed startup. IMO, there is a gendered component to whether failing at a startup is considered a positive or a negative. I know many men founders who failed at their first startup, and when investors talk about it, they say something like, "he learned what didn't work and is even more motivated to win. He's got a chip on his shoulder and won't let anything stand in his way, etc."Most women founders I know, myself included, don't talk about their failed startups for exactly the reason you identified. They don't want to draw attention to anything negative, since there are already so many biases.FWIW I don't think failing at a previous startup means someone has a problem executing, and if I were an investor, I'd much prefer a founder who knew when to fold, versus grinding it out for years. Sometimes, it's just the wrong idea, market, time, or team, and not the founding team's inability to execute.
KathleenGarvin's profile thumbnail
Thanks for sharing your story, Roxanne! As someone who's been more of a generalist in her career—lots of communications and marketing roles at startups and small businesses—it's refreshing to read your take on it. Continued success with Ethena, which I used at a past company and enjoyed :).
roxanne's profile thumbnail
Love to meet a fellow generalist and so glad to hear you've used Ethena. Always love hearing when folks have a good experience with the product!
Raabia's profile thumbnail
I love this! I often talk about the career jungle gym, too. Thanks for sharing your story! Long been a fan of Ethena! As a high-capacity generalist who also started off in national service (thank you for yours!), as I pivot to tech entrepreneurship, my generalist path that makes me such an asset has been discounted SO many times. The work we do in the public sector is high pressure, under resourced, and often comes with significant consequences for failure. Someone with the resilience to operate in that kind of environment should be an asset in a startup. But, when hiring and screening for early employees, startups still look for specialists, even though the generalist skillset will prove to be more valuable.Roxanne - I'm curious what you'd advise in those instances. How would you push back when the screener/recruiter has limited life experience to understand what value a generalist background brings? And, what companies do you know that actually walk the talk and hire folks with nontraditional backgrounds?
roxanne's profile thumbnail
I do have advice! First, look early stage (pre series A and ideally preseed). That’s when generalists are most needed. Our second hire was a generalist and she’s played basically every role at some point in our company’s history. Second, try to explain the skills you have in startup terms versus using the government language. That’ll help a team understand what you can bring yo the table. Hope that helps!
ericamarie's profile thumbnail
Your post is the reason I just joined Elpha. Anytime I see military-connected women in the start up space (even better, successfully) I get so excited. It’s rare. My cofounder and I (both military spouses) are closing up a Series A and your post here embodies so much of our experiences as well!! Keep it up and congrats.
roxanne's profile thumbnail
Oh that’s so great to hear! Fun fact, my cofounder is a military spouse. Glad to hear you’re closing your A. Huge congrats!!!
Sarabeth's profile thumbnail
I love hearing this non-traditional path - thank you so much for sharing!