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🐧 Starting a coaching business in APAC | Jennifer Ong

INSIDE: High 5-Figure Sales in 1 Month, Two Career Pivots, VC vs Bootstrapping
September 24, 2023

Meet Jennifer Ong.

Former VP at Blackrock turned fashion startup General Manager turned Founder of Ctrl Alt Career.

Today in 10 minutes or less, you’ll learn:

  • 🛍️ Jen’s Two Career Pivots & How It All Began During Covid
  • 🚀 Choosing Between VC-Backed Founder and Bootstrapping
  • 🤝 How She Grew to High 5-Figure Sales in 1 Month
  • 💪 Jen’s Honest Reflections and Her Competitive Moat

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Starting a Coaching Business in APAC | Jennifer Ong

Jennifer Ong is the founder of Ctrl Alt Career, a career coaching business designed to help unhappy professionals stuck in “perfect on paper” jobs identify and pivot into a “perfect for you” career.

Before this, Jen graduated from Columbia University and started her career at BlackRock working up to a VP before pivoting to her dream job working at fashion startup Style Theory, where she was their General Manager in charge of setting up and growing their HK business.

Because of her own career struggles, she felt compelled to start a podcast Ctrl Alt Career to help others in their careers which eventually grew to her career coaching business today.

🛣️ Tell us about your career journey from working in finance to starting Ctrl Alt Career.

I started off in finance because I majored in economics in school. When I was graduating from school, I didn't really give it much thought. I just went into roles that were recruiting actively on campus without really thinking oh, is this really the right job for me? It was the path of least resistance.

Within six months of being on the job, I realized it wasn't right for me. It was a data analytics role and I’m much more of a people’s person. I knew I wanted to leave pretty early on but I had no idea what else I wanted to do. I was held back by my preconceived notions of success and stayed at Blackrock for 7 years!

At that point, I didn't know myself at all. My entire life I've just been really good at achieving goals and delayed gratification to the point where I lost sight of who I am and what makes me tick. It took me six years to unpack my beliefs on what a successful career looks like and define success in my own terms. Externally, I also got a lot of validation by working in a big company, my colleagues were nice, and the pay was excellent, which made it even harder to leave.

The good news is I did manage to get myself out and successfully pivoted into my dream job working at fashion startup Style Theory. And that truly was the dream — I woke up excited to go to work, and never experienced the Sunday blues. And I thought — wow I can’t believe I wasted 7 years of my life working in a “perfect on paper” job when I could have had a career that was “perfect for me”.

And so during Covid, I started my podcast Ctrl Alt Career. Circuit breaker was really hard for me and I wanted an excuse to talk to people. I was surprised by the reception to the podcast — I guess it was a topic that really resonated with a lot of people. Before long, I had strangers writing to me, thanking me for creating the podcast and started to ask me for help with their careers.

At that point in time, I was also looking for ways to monetize the podcast. Podcasting was taking up a substantial amount of my time (entire weekends!), and I recognized that I wasn’t someone who could keep doing the podcast for free.

But I realized if you want advertisers, you need hundreds of thousands of people listening to make even just a small amount of money. That was too difficult at that point in time. And people were already asking me career questions, so I thought why not start a career coaching business and leverage the podcast to bring people in? That’s how it evolved.

🛍️ You were working at Style Theory full-time while working on your business on the side. How did you decide when to go full-time on the business?

I actually loved my job at Style Theory and I truly never thought I would do coaching full time. The turning point for me was when I realized I was not learning as much at Style Theory. For me, this has always been the decision making framework: am I going to learn more by staying or by leaving?

At that point, I really wanted to learn how to build a business and I had already checked off the other things I wanted to do as a part of that goal. At Style Theory, I started the Hong Kong business from scratch and scaled operations and logistics. But I still felt a lot of impostor syndrome — maybe I’m only able to do this with the support and funding from Style Theory. I wanted to prove to myself that I’m cut out to be an entrepreneur and apply the things I've learned to my own company.

And so I quit and initially joined the Antler accelerator as I was determined to build a VC-backed startup. Ultimately, I decided not to go down that route and chose to focus on my career coaching business. That was a very hard decision for me because I'm someone who cares a lot about external validation (hate admitting it, but it’s true) and being a VC-backed founder felt prestigious and exciting.

However, I had to be really truthful with myself: what did I really value? Was being a founder of a VC-backed company the lifestyle I wanted at this stage of my life when I’m planning a family? Macro conditions were also changing, funding was starting to dry up, and I saw a lot of founders under a lot of pressure to become profitable quickly. It just wasn’t as conducive to building the startup I wanted. That’s why I went into coaching.

🤝 How did you find your first customers for Ctrl Alt Career?

There were a few milestones to getting my first customers:

  1. Hiring a business coach. It was the first time I invested in my own education and it was life-changing. Before this, I had spent 6 months trying to take the business off the ground but found no success. I had no clients, didn’t know how to price my services, and was blindly creating content that wasn't converting. After I invested in my coach, I got my first client within two months and learned the biggest lesson — that investing in yourself is the greatest investment.
  2. Leveraging the podcast and social media. My first clients came from Linkedin, Instagram and my podcast. What I learned is that to make a sale is a long journey — it’s very difficult closing a client on the call if they’ve never seen your content before. It starts with them discovering you, then watching your content on social media/podcast to slowly build trust and to showcase your expertise. Most of the selling is done before they actually hop on a call with you.
Instagram post by @ongjennifer_

📈 You recently shared on Linkedin you hit a high 5 figure revenue in 1 month. What worked and didn’t work to scale your revenue?

To give context, it still feels astonishing to me to hit this number, because at Style Theory, it took me a year to make this amount. And I think being an entrepreneur has really helped me expand my money mindset to see what’s possible.

Here’s what helped me scale my revenue:

  • Increase prices. I had always been someone who was very nervous to increase prices in case I lose customers, but I was forced to do this when I started getting more clients and I got to a point where I couldn’t take on more new clients. So I started increasing my prices. To my surprise, people were still paying for my services. And the clientele actually got better — they were more motivated and more determined to do the work.
  • Launching different products. I launched group coaching to help scale my time and cater to people who were priced out of 1:1. This also helped to increase my sources of revenue.
  • Hiring a team. I really started investing in people. I hired a salesperson, a social media manager, a virtual assistant — which helped to free up a lot more of my time to focus on coaching and on business strategy. It was really hard to let go at the beginning but what I learned was that even if your replacement can only do 50% to 80% of what you can, you need to scale your time to hit bigger revenue targets. Which brings me to the next point:
  • Think and operate at the next level. If you want to run a seven figure business, you need to start acting like a seven figure business owner. And if you were running a seven figure business today, would you be hesitant to hire additional staff to scale? No way. So to get yourself to that level, you need to start thinking at that level and making decisions at that level.

🤕 What mistakes have you made in building a coaching business? What would you have done differently?

  • With every mistake, came a lesson. You could say that I hired a lot of wrong people and wasted a ton of time training and re-hiring, but I see it all as part of my learning journey — I wouldn’t know what kind of talent to look out for had I not gone through the fire.
  • When I first started, I was very nervous about sharing my business. I used to think “Oh, who am I to start this (#impostersyndrome!)” or “People are going to judge me.”  Even today, when I share so openly on social media about my career journey — I often cringe and worry what my ex-colleagues would think. But what I remind myself is that what I’m trying to do is bigger than me and if this can help someone out there not feel the way I felt in my career, it’s worth all the judging behind my back.

🫶What counterintuitive or lesser-known advice would you give to someone looking to build a coaching business?

Don’t underestimate how painful the process will be. While I was going through this process, I had the highest of highs: hitting sales targets, and the satisfaction of really helping people build a career they love. But I also had the lowest of lows.

Going into entrepreneurship, I knew the statistics — that 9/10 businesses fail. I knew in my head that it was gonna be hard, but to FEEL that statistic was something I wasn’t prepared for.

I had never experienced so much rejection in my life up until this point. I've always been someone who if I put my heart and soul into something, I generally get a positive outcome. But when it came to my business, I used to dread those sales calls in the early days. I would put my heart and soul into them, only to be rejected time and time again. You know the statistics is 9/10 will say no, but to want to pick yourself back up to have that 10th call — that really took another level of mental fortitude.

Your personal brand is your competitive moat. For example, when I was thinking about hiring career coaches, my parents immediately asked if I was scared they’re going to steal my program or clients. And yes, I was definitely worried but I went ahead anyway. Why? Because I thought, they can’t ever steal my personal story and my personal brand. And from the hundreds of sales calls I’ve been on, I realize that people come to me because of me and my story.

🏡 Where can we go to learn more about you?

I post daily career content on social media:

Or via my podcast Ctrl Alt Career, where I interview guests in Asia who have left behind a traditional corporate path to pursue an alternative career.

🌐 Beyond your borders

🇸🇬 This world-class airport is about to go passport-free (link)

🇺🇸 Remote work thrives in the biggest, fastest-growing parts of the U.S. (link)

👫 Women are more likely than men to face curveballs in retirement (link)

⚡️ 4 types of leverage to supercharge your income (link)

🏋️ My friends at MoneyFitt are improving thousands of readers investing knowledge for free each weekday. Purely investing literacy, no recommendations. You can give it a try here → (link)*

*this is a sponsored link

🤩 Words from the waddle

📆 How I can help

That’s all for today!

Whenever you’re ready, here are 2 ways for us to work together:

  1. Schedule a 1:1 coaching session for your career and wealth goals.
  2. Promote your business to 5,000+ tech professionals and founders by sponsoring this newsletter.


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Dexter Zhuang

Dexter is the founder of Money Abroad, a weekly newsletter and website that help professionals build wealth overseas. Over the last decade, he's been building and growing internet products across Silicon Valley and Asia at top companies like Dropbox and Xendit. His work has been featured in global publications like Business Insider, CBS, US News & World Report, and Tech in Asia. He graduated from Dartmouth College.

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