Bootstrapped to $3M After 20 Startup Attempts | Iuliia Shnai

Resources and Links

• Papermark: https://www.papermark.com/
• Papermark on GitHub: https://github.com/papermark/papermark
• Iuliia on LinkedIn: linkedin.com/in/iuliia-shnai
• Iuliia on X: @shnai0
• Papermark on LinkedIn: linkedin.com/company/papermark-com

Key Timestamps

(01:11) What success looked like during her PhD
(02:04) The vending machine and her father's condition
(03:52) Why she walked away from academia
(06:07) Living on $1,500 a month for years
(08:25) "I suck at raising money"
(08:44) Why confidence decides who gets funded
(12:01) Raising money after she stopped caring
(13:47) Asked for 30% for $300K
(15:52) Letting go of a team of ten
(18:03) Why she never took a break
(19:36) Ten products in a single year
(21:38) Two weeks of work, ten likes
(26:30) What kept her going through it
(28:20) The $2 an hour post
(29:57) The tweet that forced Papermark out
(32:30) What it feels like when something works
(34:04) No line between work and home
(35:58) Running $3M with two people
(38:02) You never stop living like before
(41:51) What drives her now versus then
(46:39) The next milestone, and getting there
(49:45) "Success doesn't interest me anymore"

Episode Summary

Iuliia didn't come from tech. She spent years inside a university in Finland, finishing a PhD in education technology, and for most of that time finishing it was the whole definition of success. But she'd been starting things since she was eighteen. Her first idea was a vending machine business. She went to her father for the money and he told her to bring him a business plan. She had no idea what that even was, so it never happened.

What eventually pushed her out of academia wasn't ambition, it was frustration. She found the system unfair, built like a pyramid where the person doing the work isn't the person who gets the credit. And it was slow. She'd spend two years on a paper while businesses shipped the same idea in a month. When COVID hit and the whole world moved online overnight, she looked at her own research and realized it was already outdated. She didn't know if leaving would be better or worse. She just knew she didn't want that.

Her first company was Marble, and she did what she thought founders were supposed to do. She raised. Hundreds of investor meetings, a thousand rejections, and a conclusion she states plainly: she's bad at raising money. She talks about the confidence gap, about how fundraising rewards people who can tell a big story before the story is true, and how she could never do that. She needed the revenue first. When she finally did raise, it was almost by accident, from a friend of a friend, at the exact moment she'd stopped wanting it. Her worst moment with a VC came after she'd hit the revenue number they asked for, went back, and got offered a deal that would have cost her 30% of the company.

Marble died after three pivots and three years. She let the team of ten go one person at a time, closing a product here, letting someone go there, and she describes it as slow and painful, like a breakup that never cuts clean. It's the hardest period of her life so far.

Then she did something I found remarkable. She started again instantly. No break, no beach time. She doesn't understand what a break even is. She committed to posting on LinkedIn and Twitter every day, taught herself to build with AI, and shipped ten products in twelve months. Most of them went nowhere. One she built with Marc took two weeks and got ten likes, and she didn't sleep for a week afterward. By September 2023 she was making about $2 an hour and posted publicly asking whether she should keep going.

Papermark came out of a dare. Marc had an open source project sitting in his repo for over a year. Iuliia pitched him on building something else that weekend, he refused, and instead tweeted that he'd build his own idea if the post got enough likes. It got hundreds. Then someone else saw the tweet and launched the same thing before he did, which forced him to ship. That's the company that's now at $3 million in ARR with a team of two full-time people and a few agencies.

They don't own property or a car and never wanted to. She says you never stop living the way you used to live, and that she was never careful with money in the first place because she always knew she could go get a job. The $5 coffee she buys now is the same $5 coffee she bought when she had nothing, because saving $300 out of $1,000 was never going to be the thing that changed her life.

What's driving her now is different from what drove her then. Before, it was about reaching something. Now it's about sustaining it, because there are real people waiting in support every day. The next number is $10 million, and she's honest that she has no idea how they get there, which she points out is the worst possible pitch to an investor.

When I asked how she defines success today, she said success doesn't interest her anymore. What interests her is fulfillment, not thinking about the price of coffee, being able to drive somewhere on a Monday just because she feels like it.

She also asked to add a disclaimer at the end. A lot of Papermark's customers are founders and funds raising money, and she wanted to be clear that she isn't anti-venture capital. She thinks more companies should bootstrap, and she also thinks plenty of them should raise. It just wasn't for her.

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