⚡️Founder Diaries Vol 1 Ch 3: Clara Ma, Founder of Ask a Chief of Staff - Lessons Learned Building a Bootstrapped Business
We celebrate the unfiltered BTS stories of today’s founders - from their highest highs to the lowest lows and how they powered through it all… or didn’t.
😊 Welcome to Volume 1 Chapter 3 of Founder Diaries. Now, Why Founder Diaries?
In an era where founders’ lives are glamorized and their stories are romanticized narratives of seemingly endless success, the behind-the-scenes reality of the highs and lows of being a founder often don’t come to light.
Alongside the startup with a high valuation is the string of risky decisions, maxed-out credit cards, and grueling late-night chats.
Alongside each polished story, there are real challenges, unsung heroes, and unique highs & lows that make every second of the founder's journey worth it. Or maybe not? We will let you decide.
These are the true, unfiltered short stories behind the founders of today. Enjoy :)
👋 Introducing Clara Ma, Founder of Ask a Chief of Staff - Lessons Learned Building a Bootstrapped Business
Clara went from seasoned startup operator to bootstrapped founder building an empire for the top chiefs of staff worldwide.
Ask a Chief of Staff is the premier resource for Chiefs of Staff looking to secure high-impact roles and drive results. It connects Chief of Staff talent with access to workshops taught by industry leaders, a mentorship directory of vetted former Chiefs of Staff, a network of ambitious Chief of Staff peers, and personalized career services.
I didn’t choose the Founder life.
Growing up in Silicon Valley and then later going to UC Berkeley working predominantly in the tech world, if you told anyone that you were a founder, no one would blink twice. A follow up question might be, “What does your company do?” but hardly anyone ever asks, “Why did you become a founder?”
Truth be told, I didn’t have founder aspirations when I first graduated. Even today I don’t necessarily see myself as a “Founder” with a capital F.
When I left my last job at On Deck in June 2021, I was simply burned out. Close to a decade of working at startups left me physically tired, mentally drained, and as if I hadn’t had a moment alone with my thoughts in years. I vowed to myself that I would give myself a three month sabbatical to decompress and then figure out what corporate job I would take next.
As I traipsed through Spain and had tapas for one (very sad, would not recommend), I let my mind wander and think about things I hadn’t considered for a very long time. 2021 marked the second year of my nomadic life and I started thinking about where I might want to live long term again. I thought about finding a partner and building a family. I dreamt of sleeping in the same bed for over a month at a time.
But even as I tried to keep my mind on anything but work-related things, my mind kept circling back to Chiefs of Staff, the “Swiss Army Knives” of the startup world.
I held the title myself for a little over a year at an AI unicorn: Hugging Face. After that stint, I built a community of over 400 Chiefs of Staff at On Deck. As my three month sabbatical came to an end, I realized I wasn’t quite ready to step back into a full time 9-5 (or for most startups, whenever you wake up to whenever you “finish” work). I decided to extend my personal runway by dipping my toe back in the recruiting world, which was my first job out of college.
I spent my days recruiting software engineers and product designers for the first wave of D2C ecommerce products: companies like Dollar Shave Club, Bonobos, and more. I observed recruiting for Chiefs of Staff was always a challenge for executives; those hiring didn't know what they were looking for, and those seeking the role didn't understand what it entailed.
Upon reflection, I figured that with my background in recruiting and having been a Chief of Staff before, I acquired a unique ability to spot matches between Chiefs of Staff and CEOs.
So I started up an LLC, not because I wanted to be a founder, but because I wanted an air of legitimacy to approach companies demanding my fee when I found them the right candidate.
I took a deep breath, opened up a business banking account, and announced on LinkedIn that I was in the recruiting business for Chiefs of Staff.
Almost exactly a month after launch, I made my first job placement, and my very first check cleared.
I remember yelling to myself, "THIS THING HAS LEGS!" I printed out that invoice and to this day, it still hangs on my whiteboard to remind me of that first placement. I even screenshotted it to send to my parents to say, “See? I’ll be ok!”
At the beginning of my entrepreneurship journey, I just had a piece of paper that incorporated the business. I felt like I was playing at business before the first check arrived. But that first check gave me a confidence boost that renewed my energy to double down on the business.
Soon, I found myself obsessed with numbers: the bank account balance, the number of clients, the months since launch. I also found myself thinking about what it meant to be a business owner.
Having grown up in a VC-backed world where access to capital had been relatively free-flowing and every other founder I knew or read about was convinced that they had the next disruptive unicorn idea, I felt inspired to ask myself: “What if I didn't need to build a billion-dollar business? What if I just cared about influencing ten people at a time?” If I could make the lives of ten people better, then I could grow to reach a hundred, then a thousand, and so on. I can barely count to a billion, anyway. What's the use of starting with a number we can't even fathom?
Just about a year after my launch, Erica Wenger would write a thought piece about exactly this proposition. She proposed that instead of unicorn companies, we should focus on elephant ones.
Being bootstrapped means you only have yourself as a lifeline.
It's easy to criticize being a part of the corporate world, but there's something to be said about knowing when your next paycheck will come.
As a bootstrapped founder, there was no VC check or nest egg to fall back on. Every piece of revenue is an extension on the life of the company, the only money available to reinvest in the business.
Recruiting is also highly seasonal. While I was fortunate to have made a placement in early Q4 of 2021, I was also highly aware that come the holiday season, companies would be starting to close their inboxes.
I remember sitting at my desk after I had made my first placement (a high high of the business), then suddenly lamenting the fact that I had started a business at the beginning of the low season for recruiting.
The stomach drop from high to low was palpable.
Thankfully, the elevator to the next high presented itself to me. As I was getting the recruiting arm of the business off the ground, my steady content about the Chief of Staff role on LinkedIn and Substack was attracting professionals who wanted to further build their careers and extend their networks.
For many Chiefs of Staff, being in the role is the first time they’ve stepped into this relatively nascent corporate title. Many are expected to “show up and figure it out.” There is a lack of conventional wisdom and quality knowledge available for this role because of its recent evolution within the corporate space.
It became abundantly clear to me that there was a secondary opportunity to evolve Ask a Chief of Staff. Building a community around the role would allow for new revenue. Having a more reliable stream of revenue helped to temper the highs and lows of an otherwise seasonal business.
For lessons in bootstrapping, don’t take it from me - I’ve ever only built one business, and it’s still a work in progress.
But in the year and a half I’ve spent building Ask a Chief of Staff, I’ve found a few practices that have helped me navigate the highs and lows of being a founder:
I started building a network of fellow female founder friends who I could share highs and lows with.
I take time to celebrate my wins and milestones instead of rushing past them and getting caught up in the lows.
I remind myself that building a business is hard and there’s no one way of doing it. My way might not be the best way for everyone else, but it’s the best way for me.
I spend time on the things that matter. While I don’t advise that you assign a dollar value to each email you write or start to calculate what your hourly rate looks like based on your revenue, I would do my best to keep my eye on the larger goal and make sure the actions I’m taking all translate up to that goal.
While Ask a Chief of Staff has passed its one year mark (where 50% of companies don’t), I still feel like a fledgling when it comes to business building - and that’s ok! Experiencing these ups and downs and what makes working for myself exciting and I’m looking forward to the next set of highs, lows, and elevator arrivals.
-Clara Ma
Learn more about Clara Ma and Ask a Chief of Staff below:
Ask a Chief of Staff: Website | LinkedIn | Substack
If you know someone with a unique founder story who would like to share their BTS journey of founder life - the highest highs and the lowest lows - please feel free to refer them at diariesfounder@gmail.com.
— Michelle Kwok & Christine Lu Hong (The Founder Diaries Team)