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“Don’t Make Assumptions” The 5 Lessons I Learned Being a 20-Something Founder

I had the pleasure of interviewing Oliver Alexander, Co-founder of Orchid Health and Founder of Remote.ly. By the age of 22, Oliver was…


I had the pleasure of interviewing Oliver Alexander, Co-founder of Orchid Health and Founder of Remote.ly. By the age of 22, Oliver was hiring doctors and had launched Orchid Health, a primary care clinic group with integrated mental health that opens clinics in rural areas. While running Orchid and achieving milestones like landing investment from Northwest Permanente (part of Kaiser Permanente) and changing Oregon law, Oliver became frustrated with the lack of quality workspace for remote workers and decided to start Remote.ly.


Jean: Thank you so much for doing this with us! What is your “backstory” of how you become a founder?

As a kid, I was (and still am) fascinated by cars. My family and I road tripped all the time so I started bringing a journal with me whenever we hit the road. I’d spot classic cars abandoned in a field or sitting in a garage gathering dust and I’d record their location. Next, I posted ads on Craigslist advertising my “car finder” service where I’d point buyers to cars and in return, I’d land a finder’s fee. While I didn’t earn a single dollar from this, I still remember one of the callers who said, upon hearing my pre-pubescent voice, “we need more people like you in this world and less lawyers!”. Hearing this caller, decades my senior, validate my thinking was proof to me that I could start things and be successful on my own.

More specifically, my first company Orchid Health, spun out of a business plan competition during the summer of 2012 while I was attending the University of Oregon. It was the first ever Oregon Social Business Challenge and the prompt was to “solve a social problem with for-profit business”. Only two UO students responded to the email invite; myself and my future business partner. We decided to focus on rural healthcare because it was a huge problem and there was tons of data available that quantified how, where, and why the problem existed. We were shocked to win second place in the state so we continued to work on Orchid for the next two years. Eventually, we opened our first clinic in August of 2014 at the ages of 22 and 23. From there, we cut our teeth learning how to run a business, manage doctors 30+ years our senior, and provide quality patient care. Today, we have two locations and about 3,000 patients under management via our team of 25.

Jean: What do you think makes your company stand out? Can you share a story?

Orchid stands out because we operate in a way that is almost unheard of in healthcare. Our providers see 11–12 patients/day (compared to 20–30 for most providers) and provide 60 minute new patient visits and 30 minute follow-ups. We do this while serving a patient panel that’s 60% Medicaid (low income). This long-term focus on building patient trust and relationships has resulted in outstanding outcomes.

For instance, a pregnant, undocumented, teenage immigrant showed up on our doorstep one day. She had no insurance, her family had cut her off, and she was already in her third trimester. We saw the patient same-day, had our team take time to get her setup with Medicaid. From there,we referred her to an ob/gyn where she delivered a healthy baby soon after. We also serve as the front line of rural trauma fairly often. A few months ago, a patient high on methamphetamines showed up in our lobby. She raised her shirt and exposed dozens of abdominal stitches, which she then started pulling out by hand one by one. A bloody crisis erupted but we acted quickly by stabilizing the patient and getting EMS and police on-site within minutes. I’m not sure what would have happened if we weren’t there with our doors open but I’m tremendously proud of the work our team does in times like these.

Jean: Are you working on any exciting projects now?

Yes! After running Orchid for four years, I recently moved on to start my new company Remote.ly. I’ve been a remote worker for the last eight years and I learned firsthand how hard it is to find a good place to work. Co-working offices are an option, but all the good ones are in the downtown area of most major cities, so traffic and parking is a nightmare. Working from home? Isolating and filled with distractions. So I, like many others, found myself working out of coffee shops several days per week, but the seats are uncomfortable, it’s too loud to have a proper conference call, and I got sick of feeling guilty for buying a $3 cup of coffee and then sitting there for 7 hours. No one was creating the perfect place to work remotely by the day, so I decided to built it myself.

Think of Remote.ly as the 2% milk of space for remote workers. Current co-working models (the cream) are nice but are downtown and require expensive monthly commitments. Coffee shops and working from home (the skim milk) are ok at times but filled with pain points. We’re a network of shared office spaces that have all the quality of co-working offices, but at affordable single-day pricing like a coffee shop.

Our customers buy a day pass which entitles them to receive a guaranteed seat/outlet and enjoy a free in-house barista — while being surrounded by over 1,000 indoor plants — for just $20/day ($15 for students). Our first location opens in September of this year.

Jean: Do you have a favorite book that made a deep impact on your life? Can you share a story?

Shoe Dog by Phil Knight, hands down. I’m a big fan of biographies of leaders but it’s tough to find one that’s really well written while also telling a fascinating story; Shoe Dog does this very well.

As a first time entrepreneur, in a very capital-intensive business like healthcare services, cash flow has always been a challenge. After three years of battling the cash flow, I was getting burned out. I listened to Shoe Dog as I drove back and forth between my clinics and heard how Phil struggled for YEARS trying to get bank financing for his rapidly-growing company. It was incredibly inspiring to hear how a fellow Oregonian who started young just like me was able to overcome the bank financing blockades and grow his business into a world leader.


Jean: What are your “5 Lessons I Learned as a Twentysomething Founder” and why? Please share a story or example for each.

a. Don’t make assumptions

i. This lesson applies to interactions with staff, outsiders, customers, and everyone in between. Someone not emailing you back? They’re busy, give it time and remain respectful. Customer trying to take advantage of you? They probably aren’t, so stick to your policies, and don’t read into a situation more than necessary.

ii. As a rural clinic, we had dozens of patients request narcotic painkillers. In an economically depressed area, a single prescription of these can be worth $200 so it’s natural that some people want to get prescriptions without necessarily needing them. However, after I made a few assumptions about whether a patient’s need was authentic or not, I saw a ripple effect where staff were now making assumptions about patients as well. When we were inevitably wrong about those assumptions, we lost patients and those patients told other patients. It’s much easier in management, and life, to leave assumptions at the door and operate based on facts and policies instead.

b. Prioritize physical and mental health

As a young founder, I constantly found my self-worth under attack. Whether it was a serious complaint from a staff member who felt that I didn’t communicate appropriately, or a patient suggesting that I’d “be better off running a gay nightclub” (still confused by that one), it’s easy to get lost in self-doubt. When the pressure got to be too heavy, I saw a therapist who helped me regain confidence, lead more effectively, and prioritize my physical health. It’s impossible to lead your company most effectively if you aren’t taking care of yourself in the process.

c. Take the meeting.

I’ve got a pretty busy schedule. Most founders do. But, I always make time for new contacts that request meetings. It may take me a month or two to find the time, but meetings allow me to build a relationship with someone new while also allowing the other person to feel my passion and vision. I can’t tell you how many times a meeting has turned from “ugh, I don’t really want to do this meeting today” to investor connections, better supplier terms, and unexpected opportunities. Recently, I was cramming in work before undergoing a nose surgery which would put me out of commission for two weeks. But, I made time for a 7:30 am discussion with a local breakfast group made up of business people of varying backgrounds. Before the breakfast was over, I was invited to join the board of directors for the Oregon Small Business Fair after coincidentally meeting three of their board members at the breakfast.

d. Hire slow, fire fast

At a start-up, culture is everything since start-up teams experience dramatically higher highs and lower lows than a traditional team. As such, it’s always been a focus of mine to build a culture that people want to be a part of long term through the highs and lows. However, in the beginning, I wasn’t able to draw the line between me not managing effectively vs. staff acting out of line. One employee was a big thorn in my side — after several rounds of staff complaints, I finally talked to an adviser and told her about the laundry list of complaints I’ve received about this employee. She laughed and simply asked, “why haven’t you fired her yet?” In hindsight, we weren’t the problem, the employee was. I would have saved two other positions from turning over if I’d have removed the problem employee quickly.

e. Change your perspective

I’m from Medford, Oregon. I attended the University of Oregon; a great business school but not a start-up focused school at all. Plus, my family aren’t business people and didn’t have connections that helped me be successful. Regardless, I’ve raised over $1m in funding by getting very good at pitching. My secret is that I only start pitching after I’ve grilled myself.

Before each pitch, I create a long list and title it “Questions I’m afraid to Answer”. I dig deep to compile every question that an investor is likely to throw my way in their effort to poke holes in the concept. I answer every question in several different ways so that when I do get asked those questions, I’m ready for them and can easily cite data to back up my responses. In my opinion, this is the most effective way to mitigate a young founder’s lack of experience/age and show that you’re ready to be a good steward of investor capital.

Jean: Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this. 🙂

There are so many people I’d like to do this with. But, I’ve known for years who I’d like to meet most. Someone who focuses on hugely complex problems that others seem to ignore or be too intimidated to address. Someone who works towards a better future instead of trying to sell the most ads. Someone who laughs in the face of short term gains and pours themselves totally into long term outcomes. Someone who injects fun, sarcasm, and brash confidence into their companies while not being afraid to be themselves in the public eye. Elon Musk, let’s do breakfast! My treat 😉

— Published on June 27, 2018

Originally published at medium.com

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