CPA Turned Entrepreneur: My First Year

July, 2015: I walk out of the San Francisco Airbnb offices at 3pm. I had been fired*. Two years earlier, I found my dream company and had been working in finance at Airbnb ever since.

I was at a crossroads. Imagine the feeling of going to college, except with only the fear and future uncertainty feeling. None of the excitement. I was jobless.

I had two options: Continue on with accounting or do something related to Airbnb?

A couple weeks later I got hired in an operational role for a local Airbnb property management company. I was in the midst of a complete career change and was scared shitless. I didn’t know it at the time, but this is truly where my entrepreneurial journey starts.

The first major insight I had caused a 180-degree change in my thoughts around “work from home”. In the past, I was amazingly unproductive when I tried to work from home. Now, I was at least 2x more productive. I thought it was the ‘home’ that made me unproductive, but it was the ‘work’. In hindsight, it makes total sense. Now that I do something I enjoy, working from home is a cinch.

In early 2016, I started to realize I could (and was) doing everything it took to run a business. Not only that, but I was good at it. I started to realize I had it in me. I think it is the closest I have ever been to knowing ‘she’s the one’, but not being able to explain why. I just knew business was my thing. I can do this! Every task given to me, I completed with pleasure. I started creating my own tasks (ie creating self value in the company), something I never was able to do as an accountant.

In August 2016, I was voluntarily unemployed. I quit! My original plan was to take over the world with my own Airbnb property management company. I quickly remembered being in property management can suck (complaining guests, complaining owners, complaining neighbors, etc.) and would not allow me to travel.

I pivoted to OptimizeMyAirbnb.com (originally was AnalyzeMyAirbnb.com). Unfortunately, I cannot remember exactly why or how I made this decision. But, here is an image of my first and second versions around August and September 2016, respectively…

For reference, here’s what it looks like now:

My bonus in the previous company was based on revenues. I would ‘optimize’ our lagging listings in order to appease the host and to boost my bonus. I change the cover photo, maybe moved around some other photos, maybe changes the title. Not too much. But, I noticed something. Often, these otherwise low activity listings would get reservations within hours.

I tested out this idea on some marketplaces and the first ever optimization I did was for $5 and took me about 45 minutes. LOL. I’ll always remember that. I’ll also always remember my first legitimate sale in August 2016 (thank you Airbnb Guide!).

I still had my small Airbnb property management company, but now I realized the future was OptimizeMyAirbnb.com. Belo: Airbnb Property Management was going to become more of a marketing tool than anything else. It also allowed me to continue hosting because I had been forced to stop when The Office of Short-Term Rentals fined me $1000 for Airbnbing my couch over a year earlier.

I’m off and running!

Over this past year, my daily schedule took an interesting turn. I kept waking up earlier and earlier, and wanting to. In the past, I forcibly woke myself at 6:30am, to the gym by 7:00am for one hour, and to work by 9:30am. Now, I was waking up at 6am and doing a backflip out of bed, ready for the day. Crazy! So that groggy feeling in the morning isn’t normal? Nope. So much of my life had to do with my shitty accounting job**, I didn’t even realize it! I had time to tend to my rooftop garden…

read books and focus on the gym…

and go on dates! But the thing I enjoyed the most (and still do)? Being able to run all my errands midday when there’s a seat on the bus, no traffic and no lines. For that reason alone, I’ll never work a typical 9–5 again. My life is mine.

To be clear, I work more than I did with a normal job. I work between 6am when I wake up and 11pm when I go to bed with two major differences: I enjoy my work and I’m able to take breaks at any time. Here’s my schedule:

5:55am — Back flip out of bed

6–8am — Cook breakfast, emails, read a book for leisure

8–930am — Lifting heavy weight at gym

10–5pm — Work, go to park, errands, nap, nothing

6pm — Cook dinner

7–11pm — Work, watch TV, read, drink alcohol, dates

It’s been exactly one year since I started this new life and my life has become so much more rewarding simply because I have time to focus on me. And, the best part is I’m saving 2x what I was in SF due to a lower cost of living (see “Me Now and Beyong” below). My plan is to live in South America for 6–9 months in 2018 to finally learn Spanish (I’m going to make those three years of high school pay off!)

If you are still reading, I am going to share additional insights I’ve had over the past year as an entrepreneur business owner.

Emails — Lots of emails and emails you cannot ignore. Here is my strategy: I always work from oldest to newest (bottom to top) and my rule is if I open the email, if it is a task, I have to complete it then and there. This prevents me from reading the same email multiple times and causes me to only open emails when I have the time rather than to waste time. It also prevents a buildup of older, read email in my inbox.

Coworking Spaces or Cafes — This is your new social scene. No more work happy hours or breaks, they are replaced with coworking space happy hours and activities. For me, I actually really enjoyed working from home, was productive, and never felt lonely. But, I also enjoyed getting out and working elsewhere and meeting other folks doing the same. Now that I am “traveling”, I find myself seeking out cafes more often than coworking spaces as they can be pricey. Here’s a good website to find coworking spaces around the world.

Research — 50% of my workday is research. Whether that is finding a good website developer, staying up to date on the Airbnb search algorithm, finding a graphics dude, SEO ‘expert’, learning about forming a company, reading ‘how to’ wordpress articles, accounting software, etc. it all takes a lot of time to learn. The consequences of a wrong decision make this upfront investment worth it. The research is not a bad thing, either. I have learned so damn much over the past year.

SEO — BEWARE! SEO is a double-edged sword because it’s necessary, but expensive. Also, either SEO guys are full of sh*t or very secretive. Not one could clearly communicate to me exactly what and how he does what he does. I paid a company $500 per month for 6 months and it did not get me much besides some incremental things I probably would have found out and done myself in the coming months. There are black hat (quick, but can get you in trouble with Google) and white hat (slow and safe) techniques. I was surprised to know that Google only gets about 64% of all searches. I thought it was 90%+. Bing is next at 32%.

Writing — I write for my blog once per week. This requires a lot of time and research, and sometimes can get deprioritized because it does not have an immediate ROI. I have never been a strong writer, but luckily, I enjoy writing. Writing good, SEO-friendly content is key to long-term success. I believe high-quality, relevant content will always eventually do good in the search engines. But, writing quality, optimized, structured-for-search engines content will speed the process. And, you want to speed the process.

Affiliates — I get 40% of my sales from affiliates. These are people with Airbnb-related businesses who promote me to their users and I pay them a small flat fee per sale. This world was totally unknown to me until now. I wasted about 3 months with LeadDyno (boo) while they figured out (only with my extreme persistence over many weeks) that their software was not compatible with my standard, basic website. Prime example of not doing your research and it directly costing you time and money. Because of this fiasco, one of my main affiliates never signed up with my new service, Affiliatly (yes, it is an affiliate link! But, they’re actually really easy and super cheap. I use and recommend them.).

Journalists — One of the methods I used to try and get my name out there was to email journalists after reading a relevant article about Airbnb. I introduced myself and asked if they would like to know more. I emailed hundreds of journalists trying to pitch them my story. I tried different angles. A few got back to me. Zero wrote about me. Maybe my story and company are uninteresting, but a lot of the Airbnb hosts I work with think it is of tremendous value. Tech Crunch told me they would only write about me if I had a round of financing or a new product launch (boring). In summary, total waste of time. I did get one piece of good advice from one who got back to me: do not ask them to write about you as if one email is enough for you to ask that. They get a ton of emails like this. Instead, take an alternate angle. I did and it did not work. Still sound advice.

Me, now and beyond…

I became a Digital Nomad on July 8, 2017. I sold all of my things and moved out of my $900/month rent room in San Francisco. I indefinitely travel the world while living and working in a new location every one to three months. My schedule has not changed much, but my budget has. It plummeted. Not because I am making less, but because everything is so much cheaper outside the US. Currently, I am in an Airbnb paying €12 per day for my own apartment with a balcony and parking space. I bought two prepared chicken wings from the grocery store the other day and I think it cost me €0.72. I can’t wait until I move on to South East Asia and South America. Speaking of which, please share your recommendations in the comments for any place I should visit.

*Technically, I quit. But, if I hadn’t quit, I would’ve been fired. Why? Simple. I did not like accounting and it’s hard to excel at something you don’t like. I was smart enough to get by, but eventually it caught up with me. A mentor at Airbnb who I deeply respected took notice and she had advised me the best thing for me and the company was not was not with me in accounting. I agreed, left 2-weeks later peacefully, and it was the best decision of my life. Also, I got hired back less than two weeks later in the local operations department as a contractor. Over the previous two months before I was fired, there was an internal promotion where you earned $500 in Airbnb credit per referral. I got 32 and second place got 14 (Yes, I left Airbnb with ~$15K in Airbnb credit). Some people took notice. Over the next eight months, I proceeded to be #1 in every category in the new sales role. Here are the stats from that role on my LinkedIn. If you can’t tell, I’m very proud of this as it was the first step in me understanding where my true skills were.

**I want to clarify that I have zero bad things to say about Airbnb or anyone I worked with while there — except one person :D If you are interested in working at Airbnb, I highly encourage you applying. I can’t think of a better company and culture to work for. The founders are a dream team of collaboration and I am continually impressed by them.