Welcome to Unfair Advantage.
I believe that being solo, especially in the early stages, is an advantage! And this series is the case for it, one founder at a time. For each article, I sit down with a solo founder from backgrounds as far apart as I can find, and we dig for the edge each of them built on. What did they do to get to where they are.
Somewhere in these stories, is a founder who started exactly where you are. And I am hoping their story hands you the courage to start yours.
Let’s goooo!
For a year and a half, a burnt-out software engineer tracked every dollar she spent across multiple currencies in a single spreadsheet. She was freelancing for three different companies, living out of a suitcase as a digital nomad, and had written off entrepreneurship entirely after a venture-backed startup left a bad taste in her mouth.
“Lunch Money started off as a side project that I decided to do because I was basically freelancing for three different companies as a software engineer and I missed coding for fun!”
Lunch Money is the budgeting app Jen Yip has run for seven years, entirely as a solo founder. It has been bootstrapped the whole way, and it grows without her breaking her back.
A Company Of One
For the first five years, Lunch Money was Jen and one part-time person in the Philippines only handling bank-syncing tickets. Every other support email, every feature request, every “why isn’t this transaction categorizing right,” went to Jen directly, on purpose. About two years ago she decided she did not want to do it alone anymore and brought on a core team of five, plus a small group of contractors.
These days she takes meetings only between ten and noon, Monday through Wednesday. The rest of the week is hers.
So what is her secret?
Having Fun, On Purpose
She was having fun! And I do not mean that as a throwaway.
Jen built Lunch Money for herself, blissfully unaware it would turn into anything. As a software engineer she had spent years in jobs where nobody let her design and nobody let her near marketing. On her own project she got to put on every hat at once, and she loved it!
I feel a version of this right now. Table For One is the most fun I have had building anything. I get to talk to solo founders all day, learn how they actually think, and build a community for the people doing the hardest thing alone.
When the idea or the job itself interests you, the best part is not some reward waiting at the end. It is getting to do the thing you love day in and day out!
The Money Part, Honestly
Jen was able to sustain building something that made almost nothing the first two years because she had some cushion and she was relentless about making it last. She had four years of savings from Twitter, from before it went public. She then moved to Taiwan, where meals ran three dollars and she could walk everywhere. She built tools in-house instead of subscribing to them. She tracked every dollar and she was scrappy to the core.
The savings did give her the runway, but that discipline is what stretched it far enough to fund years of unglamorous building without ever taking a cent of outside money.
“Lunch Money was never about getting rich or making money. It was always about getting back to the roots of what I like to do, which is building, coding.”
Not raising was a strategy, not an accident. She had done it before, sat across from the investors, and seen the part of Silicon Valley she wanted no part of.
“I never felt the pressure to raise. 0%.”
She did not want to owe anyone, and she did not want anyone else steering where Lunch Money went. Without the pressure to grow explosively, without a flood of users she could not handle, she could build something meant to last.
She never burned money on ads to buy her way to users. That slow early growth is exactly what let her build the product her ideal user wanted.
The moment you raise, you add stakeholders and shareholders, and you hand away some of the freedom you thought you were keeping. But not everyone can make that choice.
Family depending on you, thin savings, no way to relocate somewhere cheap, no room left to cut. Sometimes you genuinely need the money, and raising is the only door open.
So if you do have to raise, the whole game becomes who you raise from. Find angels or investors who care about the problem as much as you do, who want the same pace you want. Be picky to the point of rude. Because you should raise from the people who will protect your direction, not seize it.
Saying no to investors was the easy part. Whether anyone would ever find her app was still an open question.
Fifty To A Thousand Overnight
So how did she get people in the door?
“It was definitely luck and a lot of grit and just not giving up on getting your product out there.”
Most founders who tell you their early-traction story have quietly forgotten, or are too modest to mention, the grind sitting underneath it. Jen had a couple hundred people following her on Twitter. She had friends and family. But she kept posting about the app anywhere she could, over and over, while she sharpened it with the handful of people already using it.
And she had the one thing most founders spend years hunting for. She knew exactly who Lunch Money was for, because it was for her!
She had spent a year and a half tracking her own spending in a spreadsheet, so she was user number one, and finding fifty more people who lived like her was not a mystery. She knew where they were and how to get them.
Then one day she posted it on Hacker News. It sat on the front page for twenty-four hours, and her signups jumped from about fifty to a thousand overnight, along with a flood of emails from strangers asking whether she would build this feature or that one.
That kind of luck is manufactured. You try a thousand small things so one of them can catch, and you keep showing up long enough to be standing there when it does.
But luck does not explain the seven years since.
The Advantage She Barely Names
Ask Jen what she made that nobody could copy and she does not name a feature. She points to the sum of everything she has done, a post-seed startup, a company through its IPO, Y Combinator’s Fellowship, 500 Startups, years of freelancing for teams from seed-stage to the Fortune 500. She had to try all the versions she did not enjoy before she landed, with real conviction, on bootstrapping her own startup.
Her actual edge comes down to two smaller things she barely flags: insane clarity on her ideal users and focus.
Jen does not get pulled off course. She breaks a feature into must-haves and nice-to-haves, works the list like someone is squeezing a shampoo bottle to get the last drop, and she does not think ten steps ahead.
“I see life like a video game where you’re in this map, and the map is not discovered yet. And when you take one step forward, the next few tiles in front of you reveal themselves.”
You do not plan monetization for a side project that does not exist yet. You take the next step and see what it shows you. She stayed focused because focus was all she had.
This is the beat where I have my own scar tissues. Because my mistake was the exact inverse. I thought ten steps ahead, and it pulled me in ten directions, when I should have doubled down on the handful of users already there, already asking me for more.
If, like me, focus does not come naturally to you, here is the exercise. Talk to your users from day one, no matter how rough the product feels. People do not use things because they look nice, they use them because the thing solves their problem, so listen for what they want more of and less of and let that draw the map. And if you have nobody to think it through with, transcribe every user call, feed it to Claude, and ask it where you are fooling yourself, what you are assuming, and what you cannot see.
That is a good fix for the solo echo chamber, the one where your signal is clean but your read on it is not.
What She’d Tell You
Her advice for the founder coming up behind her is a very simple philosophy: just take the next step.
Do not dream about what you will do at a thousand users. Do not make your product scale before there is anyone to scale it for. Do the things that do not scale. Show up places. Talk to people.
“Enjoy the process. It really does go by quickly. Don’t get too attached to the way things are today. Being adaptable is the most important thing in business.”
Two years ago AI was not a factor, and now she has rebuilt whole strategies around it. She has no idea what reshuffles everything next. Neither do you.
What stays with me is where she started. A burnt-out engineer who gave up on startups, and then built one on terms she would never trade.
The map only ever showed her the next tile, and she just kept taking the step.
She has started sharing that journey on Instagram and you must follow her!
Thank you for reading all the way here. This is the first interview. Starting with the 3rd interview, paid subscribers get the founder’s full playbook: the exact tools, numbers, and systems behind the story.
If it’s time to stop building alone, Table For One is a small community where solo founders connect and trade notes with people doing the exact same hard thing. Message me and I will send you the way in!
And if this piece hit something in you, tell me your story.
The video game map metaphor is the cleanest version of 'just take the next step' I've heard. One tile at a time makes it actually doable instead of just advice.