History of Work

My first job was on a farm. I think it was introduced to me as a summer camp, but I was paid .50 cents per hour (yes, a whopping .50 cents) to plant veggies, feed rabbits, groom horses, and carry mulch around a farm just west of Boston.

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I remember that summer I slept the best I ever had. I slept so hard despite the 5:30am wake ups. My bank account grew by a hundred dollars or so by August and I felt ecstatic at 10 years old. 

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Flash forward 5 years, and I was running a monopoly of a babysitting business in my neighborhood. I had the Boxmeyers Monday, Wednesday and Saturday nights, the Sarris’ Tuesday, Thursday, and Friday, and the Bogars during the day on Saturdays. I loved getting into a routine of working as many hours as I could during the school year and in turn having just enough time to eat, sleep, and do homework. 

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Come 2015, I headed to Santa Clara University to study Economics, Entrepreneurship, and Sociology. I considered this a fancy way of saying I had no idea what I wanted to do. I worked odd jobs from manning the front desk of one of the dorm halls to helping a neighboring fitness studio run check ins and manage inventory. I loved these jobs since they introduced me to different parts of the community that I otherwise would never know about. 

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Junior year of college, after spending every summer previous nannying, I got a position as an SDR at a SAAS start up in San Francisco. I sourced 1000s of prospects for my team of account executives, a few even leading to closed deals! I loved the feeling of being a part of a team, seeing numbers trend in a positive direction, and exploring how else I could help the team after I surpassed my quota for the week. I was the only intern in my class of 10 to keep my role through the school year. 

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I graduated in June of 2019, boarded a plane to Bali that same night (a trip sponsored from working many jobs at once), and took 2 weeks to do nothing. Traveling has always been a passion of mine and one of the gifts working provides me. I then flew from Bali to NYC and rolled from the airport to my first day at work for a commercial real estate/WeWork competitor. Something that I would not suggest in hindsight (the commute path, not the company). Hired as a Sales Coordinator, I did just about anything everyone asked me to do for 8 months. I quickly befriended an enterprise account executive who was helping cool, recognizable tech companies into NYC office spaces. After 8 months, I was promoted to workplace strategist, needing to learn programs liked AutoCAD, REVIT, Adobe InDesign, etc ASAP. I loved the challenge of learning on the fly and doing things I have never done before. I contributed to $11,551 closed won ARR on the sales side and designed about 123,615 sqft of office space. 

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Unfortunately working for a commercial real estate company who had more than 200,000 sqft of NYC leases in their name did not bode well during COVID. I hung on for almost a year, as one of the last 40 employees (when I entered there were 500+ employees), but my time came to an end after a bankruptcy in March of 2021. 

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I recall this time as quite pivotal in my career. My first real job out of college ended in a way that I had 0 control over. As someone who has grown accustomed since the age of 8 to the control/freedom of having a job, I was scared and HATED not having an income. 

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I leveraged my network and had 4 consulting contracts by the following morning. My eyes were a bit bigger than my calendar space in this case but I juggled all of them for some time- one as an operations associate, one as a strategic operations lead, another as a commercial interior designer, and the last as a residential interior designer. Here is where I got really good at switching contexts, working under pressure, and managing many personalities/styles/expectations.

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I don’t think I would suggest freelancing for 4 companies and committing to 60+ hour work weeks. After a few months of juggling, I received a call from a past colleague who wanted me to come to their new growth team at the fastest growing health tech start up in the US. 

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I knew very little about the health tech space (despite loving all things wellness) and the company operated in the pediatric autism field which I also knew nothing about (despite being a nanny for many years). One thing I am a sucker for though is working under people I respect and alongside people I enjoy- this opportunity was exactly that. AND I could slim down the freelance work and stabilize for a bit. I took the opportunity in July of 2021. 

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This health tech company moved FAST, faster than any company I had been a part of so far. I also moved fast, I was hired as a sales coordinator and within 8 months was managing a team of 12 people responsible for the revenue across the US of our main service line. It was a trip to say the least. I had never managed people before nor had I ever managed revenue numbers before, but I was managing 12 people and over $13M ARR. I learned quickly, was genuinely invested in my team, and was right beside them doing the work. I made many mistakes, but thanks to the people above and beside me, I had the grace to fail and continue on. 

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I have learned that fast moving, privately funded startups are volatile. I helped grow a sales team from 5 to 40 in 3 months, and then overnight reduced that team from 40 to 16 people. Learning to manage people is one thing, but learning to manage people WHILE they do not feel a sense of security and are questioning the broader organization is another. 

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I stayed for just under 2 years and am beyond grateful for the opportunities and experiences I was given in that role. I use those learnings on a daily basis now. 

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In April of 2023 I was ready for a change, I wanted to truly connect with what I was doing and also incorporate a bit more freedom into my day to day. Similar to where I was in 2015, I didn’t know exactly what I wanted to do. Once again, I reached out to my network and got a few conversations going. I was wary of hyper growth, interested in a female owned company, wanted a role that would afford me flexibility in my schedule if I got the job done, and to continue learning as much as possible, as fast as possible. 

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One person in particular answered my text alerting them that I was in the job market within 5 seconds of it being sent. That person was Young Han. Young called me almost instantly and was enthusiastic, listened to my wants and informed me of a possible opening with him. 

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As weeks went by and I learned more about the 12 businesses Young had going on and the ways he might need help I grew intrigued. I was interested in the community of founders he was building (Owners Club) as the only way I have grown in my career thus far is through my network and I was fascinated by his coaching business where he helps small business owners reach their goals through his tried and tested method (Owners Manual Framework). 

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The only box that Young wasn’t checking was that I wanted experience working for a female founder…and this wasn’t exactly something he could change. Until he informed me that he would not be hiring me, but hiring my LLC. I was the female founder I wanted to work for. The ask to be my own LLC was a strategic one. As an LLC, filed as an S-Corp allowed me in the short term to structure my taxes advantageously and in the long term, it opened the doors to possibly owning businesses with Young. 

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This was once again a pivotal moment in my career as I spent the following weeks starting my own company, Raglan Studio LLC, filing it as an S-Corp, getting financially organized, and signing my contract to work with Young on Owners Club. 

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I am currently the Manager of Strategy and Operations and I have 6 of my own coaching clients that I take through the framework on a weekly basis. Leveraging knowledge from my time at hyper-growth startups and learning from Young’s methods, I get to help small business owners scale profitability, become operationally efficient and build financial visibility. It very much feels like I have a lot to learn, but for the first time I am obsessed with every part of the role and look forward to every zoom meeting and slack message as the businesses I work with are amazing.

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Here are my key learnings and insights during my first 90 days:

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1. Not having investors allows owners to control speed at which they move and priorities they want to accomplish.
2. Test/Track/Test/Track until you find something that works and then stick with that. 
3. Young always says it, simplicity is scale.
4. Having a clear view of financials can tell you so much about a company. Be financially literate and learn how to produce simple financial projections based on smart assumptions.
5. Accountability and being realistic about what you can accomplish and what will move the needle is 80% of the battle for founders.
6. If you have a strong network and a strong ability to build on this network, you actually don’t need to be the smartest person in the room to be the best positioned person.
7. Running a business doesn’t need to be overwhelming if you have a method/process.
8. Stop doing a million random things and just focus on the 20% of the things that will produce 80% of the results. 
9. Managing people (phase two of the framework) is so damn challenging. But there are methods to make it work.
10. Be unemotional! So often we hear that business is your baby but life will get lot easier if you can untie your emotions from your business.
11. As a doer, I have had to learn that a good coach will only ever do 49% of the work with the client. A coach is a supporter, an empowerer, and believes in the owner. The owner is also the subject matter expert of their business, so I am merely a course corrector, resource, and cheerleader. 

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Coaching businesses to their own financial freedom, building a community of owners, and working in an org that is essentially coaching me has been the most rewarding thing I have done thus far. 

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Each new year I pick a single word that will guide my intentions for the 365 days to follow. This year my word is ‘cultivate’. I want to cultivate things that I will be proud of in the future, be around people that I will grow with, and live a life that will provide bountiful gifts in the future. I am doing just that at Owners Club. There are a million more things I have learned but that will come with time, as this very much feels like the beginning :) Subscribe to Owners Club’s monthly newsletter so you can stay up to date with the Club and my journey coaching Owners.

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