Ollie: Conversation with Christopher Bledsoe

Ollie: Conversation with Christopher Bledsoe  Chris always knew he wanted to be an entrepreneur. After graduating from Georgetown with a business degree in 2003, Chris went on to work for J.P. Morgan and Lehman Brothers where he accumulated experience, insights, and network in the business and financial world. In March 2011, Chris took the entrepreneurial […]

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Ollie: Conversation with Christopher Bledsoe 

Chris always knew he wanted to be an entrepreneur. After graduating from Georgetown with a business degree in 2003, Chris went on to work for J.P. Morgan and Lehman Brothers where he accumulated experience, insights, and network in the business and financial world. In March 2011, Chris took the entrepreneurial leap to start Ollie, an all-inclusive co-living company after having identified a pain point in the housing market. 

Ollie’s concept is refreshing and pleasant. Instead of just paying money just to rent a cold block of space, Ollie offers you a line of services from getting your kitchen cleaned to your empty shampoo bottles replaced. In other words, you are not just paying for space, but also a professional personal butler. 

“I love what I am doing and would not have it any other way”, says Chris.

  1. Tell me a little bit about what you did before Ollie. Did you always know you want to be an entrepreneur? 

I’ve felt entrepreneurial for as long as I can remember. At heart, I am a creative. There are different kinds of creatives: I’m not particularly creative when it comes to arts and crafts, but my creative expression comes through entrepreneurship and problem solving. I am wired to view problems as opportunities. 

It’s quite easy to tell from my work experience: every job I’ve done has allowed me to express my creativity and love for solving problems. 

Both my father and grandfather were very entrepreneurial. My grandfather and his friend started a candy business together, so growing up as a kid, I was always able to run through the candy factory. That was a fun way for me to get very exposure to business very early on. My father very much encouraged my brother and I to see problems as opportunities, and to think big. 

2. You worked in finance before founding Ollie. Tell me about that experience. What did you learn?

By the time I was graduating college I had a decision to make: I can either take my college business project full time, or I can accept my offer from J.P. Morgan. 

As entrepreneurial as my father is, his advice at that time for my brother and I was, to “take the safe route”. He wanted us to learn as much as we can in a big company and build our credibility. 

The funny thing is, by taking the “safe” route, I ended up at Lehman Brothers and my brother ended up at Bear Sterns. We all know what happened there. So one of the biggest lesson for us going into finance is: what we may perceive as safe is not always safe. Change is the only constant. 

3. A lot of college students today are also hoping to work in finance or consulting for a few years before starting their own companies. Would you recommend that path? 

Everyone is at a difference place in their personal development and their perusal finances, so this really is down to the individual. 

Personally for me though, it was a good choice to first work in a big finance firm. I always wanted to go to business school, and by joining a structured corporate with a training program and mentorship, I was able to gain all of what business school had to offer, while getting paid. I was also able to start saving money to fund my side-business in the early days. 

I was getting paid to learn things I could not even learn from business school.

Generally speaking, it’s perceived safer to join a big corporate than a startup, because you never know what’s going to happen to a fledgling company. However, even if the startup you joined does end up failing does not necessarily make you a less marketable as a candidate in the workforce. Even when a start-up goes under, the skills you have developed will not go away. Usually, those who are really qualified and confident in their abilities are usually more willing to summon the risk of joining a startup, 

4. There’s always a lot of doubt when you are starting a new business. How did you decide to take that entrepreneurial leap?

Eventually I had to decide if I believed enough in my side-hustle to turn it into a full time gig. I had a college side-hustle, which I opted not to turn into a full time job. I had a hide hustle as an employee, and as you can see, I did decide to turn into into a full-time job, which is now running Ollie. 

I wanted to take a calculated risk. By the time I was starting Ollie, I’ve created a small safety net for myself, a network of some sort, and a lot of knowledge in the finance world. For me personally, I wanted same safety before I was willing to take the leap.

More importantly though, I really believe in the idea of Ollie. If I fast forward a few decades and look back on my life, I know that I will regret not pursuing my idea. There are very few original ideas, and I think there’s an inevitability to my idea. I would not be able to live with myself when I have to tell my grandkid: “Oh, I had that idea too. But I decided not to pursue it.” I’m okay with trying and failing, but I’m not okay with not trying and seeing it succeed in someone else’s hand. 

5. What were some fears you had when starting Ollie, despite your conviction?

I convinced my brother to leave finance and to pursue the opportunity with me. My brother was younger in his career and didn’t have the same kind of safety net as I did. The consequences of Ollie failing would be more acutely felt on my brother Andrew than me, because he didn’t have the pedigree I had. In fact, he even sold his home to fund the business. If the company had failed, he would have lost everything. 

So I had a fear for my brother. The VC industry didn’t exist yet back in 2011, so we had to bootstrap our business. It took us 3 years and 400 meetings with developers before we got our first yes from investors. In order for my brother to continue the venture with me, he had to get a side job. It was 1.5 week before we got our first yes, and I remember he was filing out an application for baggage handling jobs at JFK airport, just so that he could have some income to sustain himself. 

6. How did the idea of Ollie come about and what did you see in the micro-housing market?

Although I was working in finance, I was covering on the consumer goods industry. I had the benefit of a consumer marketing background and understood how good companies were built. It was by identifying a pain point, coming up with innovative solution, and marketing the solution to those who were feeling the pain point the most. 

I was covering Kellogg’s, the cereal brand. They observed that consumers were chopping up fresh strawberries and adding them into their cereal in the morning. To solve the problem, they launched Special K with strawberries, which is cereal with dehydrated strawberries in them. However, the cost had gotten up, so their solution was to shrink the box in order to keep the price the same to make the product competitve.

I tell this story because it has everything to do with the idea of micro-housing. The housing market has become very commoditized and has been shrunk down to a white box. People are paying very expensive rent for a space and a space only. It takes a lot of time and energy to clean your living space, take the trash out, and there are so many messy chores that come with living,  We wanted to solve this problem by elevating the experience of living. Living should not be full and painful; it should be fun, satisfying, and comforting. 

We know our consumers can’t pay more, but we don’t need them to pay more. The lifestyle we provide compensates for the small space. With Special K, it is trading volume for the strawberries. In our case, it’s trading living space for a hotel-style living experience. 

7. What are the biggest challenges facing Ollie right now and how are you guys doing in terms of growth?

The biggest challenge is that we are operating in a supply-constrained market. The consumer demand for what we are doing is very, very deep. We don’t even have to do much advertising ourselves. However,

the problem is that we can’t build enough supply fast enough. 

Real estate investors are extremely risk-adverse, especially if they are investing in gateway cities’ housing. Constructing these buildings usually require a good leverage, and the lender is even more risk-adverse than the equity investor. For this conservative capital controlled industry, innovation is not the life blood. Innovation means change, and change means risk. 

As a result, I’m now focusing on meeting with institutional investors and demonstrating to them that co-living is actually less risky, not more risky, than the conventional housing model.  

8.  What’s one piece of advice that you would give to your college self?

Persevere and surround yourself with people who believe in you but also challenge you.

It took us three years and 400 meetings to get our first investor to say yes to Ollie. That’s a long and draining process. Had I taken the advice to fail quickly and embrace failure, I would not have gotten to that 400th meeting. But it was my conviction in Ollie as well as the support from my wife that kept me going.

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