🆙 Falling Up

Trying to Make Sense of an Atypical Career

Welcome to Startup ROI, where I, Kyle O'Brien, share European Tech insights from my perch in Paris, France. You can expect to find articles covering startups & ecosystem trends, interviews with founders and investors, as well as updates on in-person events for community thought leaders.

Want to sponsor or collaborate? 📩 bonjour@startup-roi.com

Join hundreds of curious minds & follow for in-depth analysis:

---

More than likely, the holiday spirit has brought on a bout of nostalgia. Among other things, I started to reflect on my career up until this point. As a child of the 90's who spent his elementary years in Montessori school, I had no choice but to embrace the quirky poetry of Shel Silverstein. And for some reason, the other day my mind conjured up his 1996 collection of poems — aptly titled, Falling Up — when trying to characterize my career path.

Most of my friends and family would consider me a “planner” — I tend to preemptively lay out my path forward, personally and professionally on a 1-3-5 year time scale. This has been a helpful framework and has definitely catalyzed much of my forward momentum. But in many respects, I've been falling up for years. This guided chaos has been a defining feature of my progression and today I was hoping to connect the dots to see if there was anything to find in retrospect.

To be clear, this is not intended to be an exercise in navel-gazing, nor is it a prescription for building a fulfilling career. But in a world where career progression is less linear and optionality is king, I hope this piece will bring some sense of solace to those earlier on in their journey. Plus, it's kind of fun to look back at the missteps, learning experiences and combination of opportunity and preparedness (i.e. luck) that landed me here today.

The Intern

Like many high school and college students, I pursued internships as a way to get some real world experience on my résumé for entering the actual real world. Some were formative, some were boring, but all provided a worthwhile lesson, even if that lesson was to eliminate a future career path. The smorgasbord of roles I held is almost comical in hindsight. Let's review:

GoBible

My first internship, against all odds, was with a direct to consumer digital audio Bible business. Let me explain… My high school AP Economics teacher (and advisor) had a side business he built with a friend of his. It was called GoBible. Keep in mind, this was in 2009 — the iPod touch was recently released and Spotify hadn't made it way to the US yet so streaming wasn't quite part of the popular vernacular. I should also mention, this was not a passion (of the christ — couldn't help myself…) project. Both my teacher and I are atheists. There just happened to be a market demand and we were filling supply.

The supply, in this case, was a pre-loaded mp3 player with essentially one track: the King James Version of the Bible (I think you could actually choose from among several versions — we had like 3 SKUs!). Any consultant worth their salt knew this business would be dead in the water in less than 10 years — it is, in fact, dead today. But in the near-term, devout Christians nationwide were buying (and sometimes returning) GoBibles left and right. I know this because I handled returns (verifying defects and issuing reimbursements), processing invoices from our supplier (probably some factory in China), and printing mailing labels to send products through the post office. Despite joking about the hilarity of this business with friends, my access to Quickbooks told another story. They were minting money on a side business with little to no overhead (aside from a closet full of inventory and some annoying trips to the post office). My teacher was fairly strict on process and chewed me out for cutting corners. In hindsight, I got front row seats to a budding eCommerce company.

Lessons:

• You don't have to be passionate about a space to start a business… but it helps

• You can produce a cash cow with a relatively small business assuming you find product market fit and a reliable distribution channel

• Customer service can be brutally painful, but you learn a lot on the front lines that will stick with you in future roles

LOL found an old image of the product — still can't believe people bought these things!

Corporate America

In college, it somehow got drilled into me early on that the route I would have to take is in finance or consulting. I didn't really question it — I just assumed this was the appropriate career path. So for a couple summers I fell in line and secured internships, mostly to signal to my parents that I wasn't a complete slacker. The first one was at a boutique wealth management firm in St. Louis, where I went to High School. It was very unstructured and I mostly did some light research on investment policies and played Robot Unicorn Attack on my iPhone 3G (IFYKYK). The second was at New York Life Insurance Co. — this was partly to appease my parents but mostly to live in NYC with my buddies who went to NYU and experience the Big Apple first-hand. This “coveted” (and evidently competitive) internship program was mostly grunt-work like claims processing and handling projects for senior analysts. If I remember correctly, this was the summer that “planking” was trending on social, so I put a fair bit of effort into finding creative places to plank in my free time away from the cubicle. Ultimately, I learned that corporate America wasn't for me, but living in a major metropolitan area was.

This has to be one of most legendary planks — and yes it is me in tacky business attire outside my cubicle

Lessons:

• There's no shame in taking an internship for a reason outside the internship itself — in my case, living in New York City was a remarkable and formative experience that set me up for future endeavors

• Get what you can out of any work experience, even mediocre ones. But don't hesitate to have a little fun.

• There's a fine line between brute forcing your way through an experience and simply wasting your time — figure out that boundary

RapGenius

In my last piece — Revaia-lations — I mentioned writing a piece on the value of cold outreach. Well, this particular experience was the turning point for me. I can still remember this moment like it was yesterday. My Mom had sent me an article on this up-and-coming startup run by Yale grads intent on building an explanatory layer of the internet via rap lyrics. Like many, I was a skeptic, but also a hip-hop fan so I perused the site for a bit. The nascent community platform allowed users to annotate lyrics and uncover the meaning behind the music. The distinctive site with a black background and yellow highlights became a regular internet destination for me. I began slowly racking up IQ points (credits) to lend me some digital clout, at least within this corner of the internet. The Aaron Sorkin film, The Social Network, had come out just a year earlier and I thought to myself maybe these tech nerds will want some help developing this product. But how? I didn't know how to reach them, I didn't see any job postings and frankly I didn't feel qualified to actually help. But then it happened: I spotted the “Contact Us” button hidden at the bottom of the homepage.

I crafted a quick message and hit send into what I expected to be the æther. I figured it would land in some trash inbox that no one checks. I closed my laptop and went to bed. I woke up the next morning to a phone call at 7am from an unknown number. Groggy and disoriented, I picked it up… Hello? It was Mahbod Moghdam, one of the founders of RapGenius. He wanted to talk. He offered me an opportunity to write a blog post, encouraged me to “get my RapIQ up,” and dangled the notion of a potential internship that summer. In Malibu, California. Before I knew it, the call was over and I wasn't sure if I had dreamt the entire thing.

Clockwise Starting Top Left: Young me & Rick Ross at the BET Awards after party; young me teaching Schoolboy Q how to annotate his own lyrics (part of the “verified artists program”) — fun fact, this is the studio in Compton where Kendrick Lamar recorded good kid, m.A.A.d city; young me saying hi to A$AP Rocky after his show — I handed him a RapGenius poster he held up on stage; a quick picture with Danny Brown at Moma PS1 following his show

Following a convincing sales pitch to my parents (this was quite a departure from my previous internships), I drove across the country to effectively join a stranger in a house in Malibu building a rap lyric website. It was one of the best early career decisions I made. This, like many previous internships, was somewhat unstructured. The difference was that I was highly motivated and eager to contribute wherever I could. After all, this was a tech startup at the intersection of culture and media. At the time, there were the three founders and a few developers working on the site in NYC. Everything was new, untouched, and for the most part, fair game.

I built mock-ups for new pages and features (I didn't know at the time this was a PM task), I reached out to music journalists and influencers to identify partnerships and drive visibility (PR/Marketing), I worked on actually annotating the site to improve the quality of content (community management, moderation and user testing). The cornerstone project, however, was what we dubbed the verified artists program. We wanted to build something like the Twitter Blue Check, but for artists who gave fans a peek behind the curtains to their lyrics and process. We hosted artists, showed them how to use the platform in real time, and eventually it stuck. Rappers were thrilled to share more with their fans, oftentimes they smirked when they saw an annotation that was correct (or hilariously incorrect) on their song page.

We started to host parties and attend events. It was a true growth hacking wild west story and I'm grateful I got to be a part of it. I continued working for RG back at college and even hosted the founders for a live debate with faculty and visiting experts on Hip-Hop, Education and Society. The semester I graduated, I saw a TechCrunch article that RapGenius had raised $15M from Andreessen Horowitz (a crazy amount in 2012) and it dawned on me how important this experience would prove to be. In hindsight, it is all still very wild to me.

Lessons:

• Never be afraid to send an unsolicited message through a contact us page (or Twitter DM or make a cold call etc.) — you never know the outcome and the worst that can happen? Nothing at all.

• Make yourself useful. Whatever the role, find a way to contribute, especially at early stage startups. There is always something to get done and many things that people simply don't want to do. Find out what you like or what you're good at and start chipping away. You'll likely be rewarded but if not, you learned something.

• Don't worry too much about the end result. Enjoy the process. I was desperate to land a job at RG after college but they simply didn't have a spot for non-coders. I took it personally and felt lame that I was heading into a “big” company instead of a trendy startup. Today, I'm grateful my path diverged but also happy to have been a part of the early days at this oddball startup.

The Graduate (Entering the “Real World”)

Following the vast array of intern experiences, I landed somewhere on the middle of spectrum: Big Tech. I wasn't slaving away on Wall St. as I once assumed was my destiny, nor was I involved with a rag-tag team of 20-somethings looking to build the next Facebook. Salesforce, it turned out, was a great entry point into the real world, a young, fun and casual environment overseen by real grown ups and a functioning corporate culture.

I don't have much wisdom to share here other than I kept at it with the networking, making myself useful and pouncing on unexpected opportunities. I largely credit my first promotion to my “Salesforce Got Talent” performance (watch below) in which I incorporate the story of my life as a post-grad sales intern into a soccer juggling act. I don't know how I pulled this off, but I became a minor celebrity in the Chicago office as a result (read: highly networked).

I was also the reigning office ping-pong champion and schemed my way to Dreamforce — the annual Salesforce conference in San Francisco — by cold DMing a department head and volunteering to help his team out with their booth (much to my boss’ chagrin). I've got a total of 3 Dreamforce's under my belt now — the first was the biggest hurdle. Eventually, I took a number of Salesforce Admin/Developer exams and pivoted from Sales to Solution Engineering (technical pre-sales), a fairly unconventional route at the time. As a result, I started to rise the ranks and acquire tons of experience running discovery calls and demos in front of larger and more complex customers.

Salesforce was a great launching pad. I'm glad to have gotten the discipline and structure of an established company while exploring roles that would influence my next steps. Those next steps took the form of a series of startups which I'll touch on briefly:

Nanotronics

A Peter Thiel backed semiconductor inspection company was not where I imagined I'd find myself just months before arriving here. Ironically, I was poached by their CRO when I delivered a demo to their team as a Solution Engineer at Salesforce. I had always been a science/deeptech nerd at heart and this presented me with an opportunity to help build a sales & solution engineering team from scratch, travel around the world to sell into chip fabrication facilities (I wore a lot of bunny suits — see below), and work alongside some incredibly talented scientists and engineers.

The “Bunny Suit” — the work uniform of researchers in clean rooms around the world

We sold AI-enabled white light microscopes, a hardware/software combo designed to identify microscopic defects across the production line in a chip fab. It was a fairly revolutionary idea (most facilities had one big laser scattering machine that scanned output towards the end of the production line) that promised to improve yield and thereby save costs. It also proved to be a tough market to break into — highly complex, incumbent competitors had footholds and expensive capital installed with long lifetimes, and we were unproven/new to the market. The company has only advanced since I decided to leave and it's been cool to track their progress from a distance!

Hivebrite

Before my next startup I actually returned to Salesforce (what they call a Boomerang 🪃) to join their Community Cloud team. But I still had the startup itch, and now it was coupled with a desire to move abroad. Around this period, I found out I was eligible for an Irish passport (long story). Once I got approved, I was able to live & work in Europe Visa-free! So I went to my old playbook: cold outreach. I looked into Paris’ startup ecosystem (at the time, Station F was the only real hub) and found the contact info for every founder that had gone through an accelerator program. At this point, I wasn't surprised when I got some replies. One of which was from Hivebrite, an emerging online community platform, not dissimilar from what I was working on at Salesforce.

Following a few Zoom meetings, a coffee in Bryant Park and a week with the team in Paris, I signed a contract and moved across the Atlantic. I arrived on a Friday, started on a Monday and quickly realized I didn't have a formal title — not that uncommon for a small startup. After three months I took on “Head of Customer Success” and was managing a team of 6 people, mostly older than me, all French. This was a learning experience, and then some. Over time I built their trust and we rode the wave of a classic blitzscaling experience: we raised a $25M Series A from Insight Ventures, opened an office in NYC, went from 25 to 125 employees, and signed some major customers. It was exhilarating, exhausting and eye-opening all at once. As we entered the pandemic, I was ready for a new adventure.

A little bit of this, a little bit of that

I left Hivebrite to join Ausha, a podcast hosting and distribution company based in Paris (similar to Anchor.fm or Acast). Unsurprisingly, this was a role I created myself (they had no job listing). But through the magic of cold outreach and a clear passion for media and technology, I ended up spearheading their international development strategy. Fairly quickly, I came to the realization that I was less interested in building a podcast platform and more interested in starting a podcast (and a newsletter), which I ended up doing with Startup ROI.

I left to focus on writing and podcasting, giving myself a 6-month runway to find “product-market-fit.” It was daunting. I didn't even have a Twitter account, let alone a Substack following (still working on growing both, btw). But consistency over time led to some cold outreach coming my direction (for once…). Entrepreneurs, creators, VCs and tech ex-pats started to get in touch. As a result, I've been able to consult for a prominent growth equity fund, interview amazing European founders and investors, advise startups and host a monthly dinner series for content & community leaders across the ecosystem. Oftentimes I attribute this to pure coincidence. But laying all this out in front of me paints a clear picture: put stuff out there, reach out to people you admire, and try new things. Not everything clicks, but when it does, the juice is worth the squeeze.

Lessons:

• Despite my penchant for planning, the career I have now could not have been predicted by any Oracle at Delphi (let alone 18-year-old me). Make plans, execute against your objectives, but leave room for some detours. It's worth it.

• Cold outreach and risk-taking isn't just for the young and hungry. That tactic has served me well into my 30s and people tend to be responsive, friendly and reactive. If there's something you want — an opportunity, a job, a collaboration — slide into a DM or 2 and see what happens. You really never know.

• Imposter syndrome is only as real as you make it. For years I was concerned I was out of my depth or clearly unqualified for certain roles. Sometimes your superpower ends up being something you take for granted:

  • I had no business cooking up a “performance art piece” involving a soccer ball in front of the 300 people when I was a post-grad, entry-level employee with my job on the line. For that matter, it probably wasn't recommended to commit hours a week playing ping pong with VPs. But I left an impression and built relationships that helped me chart my atypical ascent at the company.

  • I didn't have a PhD in materials science but I was an effective science communicator and curious sales person who enhanced my peer group with business skills they lacked and related to customers who weren't accustomed to getting the time of day.

  • I had neither been on a customer success team nor managed people in my life. Then I inherited a customer success team. In France… It took time, effort, empathy and a lot of personal/team development. But we ended up building a strong and successful organization that helped drive decision-making and strategy at a growing startup.

  • I hadn't ever written a newsletter. Not even an essay for the school paper or a submission to the university comedy club. Why should I expect to build a following talking about the French/EU tech ecosystem — nobody has heard of me and my opinion really doesn't matter at the end of the day. I wouldn't call Startup ROI a “runaway success” by any means (my original goal was the become the Packy M of Europe). But it's landed me where I am today. For that, I'm humbled and grateful.

Investing in the/my future…

Hopefully, this walk down (my) memory lane helped you reflect on your own career path. Or maybe inspired you to do something new or try something different. Or keep doing exactly what you’re doing! But the tail end of this saga is yet another teaser about what I'm doing next. I have an upcoming piece giving all the juicy details. In the meantime, I wanted to take the mystery out of it. Partially because I've held on too long and partially because it's real now and I'm ready to take action!

I'll be join Rand Hindi as his Chief of Staff for his angel investing practice focused on early stage deep tech startups. If you didn't get a chance, you can listen to my interview of him here. He's a 2x deep tech founder, current CEO of Zama.ai, and a Top #5 Angel Investor in France (according to Crunchbase) with 30 portfolio companies to his name. Together we plan to scale his funding capacity and continue investing in pre-seed/seed rounds in the EU/US with a focus on:

1. Next Generation Computing

2. Blockchain, Privacy & Encryption

3. AI-Enabled Biotech

4. Other: Space Tech, Climate, any scientific breakthrough worthy of being commercialized!

Did I mention he has a Substack as well?

---

More to come on this! Thanks for reading (btw, I'm going to keep the newsletter and the dinner series running — so hit me up if you want to chat!)