This bootstrapped founder hit $350K ARR in 14 months

And, how you can, too

Author

Sweta Govani
July 25, 2024

Ashley Chang’s bootstrapped startup, Sundays, surpassed $350K ARR recently. Sundays is a tech-enabled executive assistant service for working parents.

Ashley has been a part of the Founder-Led Marketing Club* (FLMC) - a group for smart, kind founders running GTM micro-tests on their journey to $1M - since December 2023. When she joined, she had less than 10 customers and only early signs of revenue.

In March 2024, ~3 months in, she hit $100K ARR. In a FLMC member session in April, she shared her journey on how they got from 0 to $100K. In this issue, I’m sharing the biggest takeaways with direct quotes from Ashley.

Learn about Ashley's journey from 0:

Discovering an idea worth pursuing 

Prior to Sundays, Ashley and her co-founder worked on an AI customer support tool. They spent 2 months building the product. “AI can be addictive to try to figure out. That overshadowed the building the business part of it.” 

When it came time to get customers, Ashley struggled. She shared, “I don’t care about pushing this thing forward enough. What problem do I care about that I would be willing to do this for? I had been jealous of people working on parenting. I remember thinking, ‘for my next startup, I want to work on parenting’.” 

When they decided it was time for something new, Ashley jumped to build something in parenting. That was the seed for Sundays.

Marketing-first approach to validating her idea 

With her second idea, Ashley decided to take a marketing-first approach. As her first step, in May 2023, she set her first micro-goal: “Can I get 20 people to enthusiastically talk with me about this problem?". She reached out to every parent she knew. Parents were very willing to speak with her. This was her way of validating the problem was painful enough.

She also did a round of traditional user interviews. At the end, she would pitch the solution they were considering developing. This is how she validated the positioning. She complimented this with market research for what other companies are doing in the assistants for parents space.

Based on this research, by the end of the month, they decided to pilot a concept. Ashley continued her iterative marketing-first approach. “I was really nervous from the previous idea that I had worked on where I didn't get any commitments to pay for it upfront. I needed to know if someone would pay for this pilot, and the only way I could is if they actually paid.” She reached out to people she had spoken with and asked them if they’d be willing to pay for it. 

User research interviews for direct sales 

Ashley didn’t stop the conversations with her customers. In the months that followed, Ashley spoke to 200 parents who shared their unique parenting challenges and struggles. 14 months later, Ashley continues to have conversations with parents regularly. 

As a previous product manager, Ashley has experience with user research. “I was really used to traditional user interviews where you're gently leading people towards trying to figure out whether they will buy or not. I think that it gets you good information. Once you have enough information to figure out what you might want to sell, I think you have to switch to trying to sell. This is what helps you move quickly to get paying customers early.”

Staying close with her target audience has played a critical role in Sundays’ success. For example, it directly feeds into her strongest channel - LinkedIn. “Whenever something stands out to me in user interviews, I bold that. I use that as the hook on LinkedIn. It also gives me more confidence to post.”

Micro-testing to 10 Happy Paying Customers 

  • The first customer for Sundays was someone who Ashley used to work with. While they weren’t friends, they had a pre-existing relationship. 

  • After this, Ashley set another micro-goal: “get 1 person who doesn’t know me to pay for Sundays”. 

  • One of the first marketing channels they tried was very non-traditional: They put up flyers around San Francisco with QR codes. A few customers came from this. 

  • The next 6 Happy Paying Customers came from referrals from the original customer. She had posted on LinkedIn and people came through that. 

  • Around this time, Ashley joined the Founder-Led Marketing Club* and decided to start running experiments. 

  • She saw the potential in LinkedIn so she decided to try posting. The next 3 happy paying customers came from her posts. LinkedIn continues to be their strongest and most predictable channel even after they’ve surpassed $350K ARR.

  • With negligible churn, and incredibly happy customers, referral is a strong channel for Sundays. However, it isn’t predictable. Ashley even tried a structured referral program with monetary incentives for current customers. That didn’t result in new customers. 

  • Ashley is running new micro-tests to discover the next predictable acquisition channel in their GTM playbook. She’s also working on email including automation to improve engagement and conversions from their existing audience.

A manageable marketing routine that works

As someone who did not have a marketing background, Ashley needed to figure out a routine that worked for her. She shared, “I had read Traction, met with marketer friends, and even set up marketing time blocks. But, I had no idea where to start so I wasn’t using that time well and wasn’t doing sufficient marketing. I needed a framework and structure to figure out marketing on my own.”

“When I found the Founder-Led Marketing Club*, I loved the idea of micro-tests. It helped me develop a routine that works for me.” In a recent post, Ashley shared her marketing routine broken into monthly, weekly, and daily buckets: 

Micro-testing new ideas

Ashley intentionally creates time for new experiments. She shared how she makes this manageable. “Our overall goal for the year is to pay ourselves enough to keep working on Sundays. All our other goals are 1 month maximum. For most marketing goals, even 2 weeks can be a great timeline. For example, I was scared of LinkedIn. I decided to try it for 2 weeks. As long as you are structured and committed to doing the work for the time period, you can learn a lot in 2 weeks.” 

To some, this might seem small. But Ashley shares how this worked for when she first tested LinkedIn. “Momentum is so important so feeling like I got something done every week is important. I am motivated by having things done. My first goal was to figure out if people would like my content enough so I wouldn’t feel negatively about posting. We also ask how people heard about us and LinkedIn is increasingly the top source.”

Making time for marketing as a founder

Many founders struggle to find the time it takes to strategize, learn, and execute on marketing week after week. 

Ashley shared, “what has helped me is the realization that if I don't do marketing, the company doesn't exist. After maintaining our current client relationships and making them happy, marketing is the most important thing I do. If I don't do marketing, no one does it. And if we don't find new customers, then we don't have a business. Readjusting my own mindset to understand how critical it is has helped me prioritize it.”

—

If you read till the end, firstly, thank you! Was this newsletter helpful in your 0 to 1 marketing journey? What follow-up questions come up for you? What could have been cut? Hit reply and share candid thoughts so I can write more of what is most useful for you!  

—

P.S. (*) Interested in joining the Founder-Led Marketing Club and GTM micro-testing? Here are 3 options based on your traction and priorities: 

  • Focused on getting your first 1-10 Happy Paying Customers? Join the upcoming cohort for the 6-Week Founder GTM Bootcamp. Only 4 spots available. 

  • Have early traction? Join a Peer GTM Group with weekly/monthly structured sessions for accountability on your experiments, and learn from peers’ GTM micro-tests. 5 spots available. 

  • Need help designing your GTM micro-tests? Work with me via weekly 1:1s to prioritize ideas, design micro-tests, and execute. Only 2 spots available. 

P. P.S. Have follow-up questions for Ashley or me? Add them here.