Are you afraid to ask for what you want? Some requests – of ourselves and others – can seem so great, and the chance of compliance so small, that we never make them at all.
But as the saying goes, “If you don’t ask, you don’t get”.
Take Dutch entrepreneur Danny Postma, for example. After 30 years of learning new skills and enquiring after every opportunity he encountered, he built an AI startup in eight weeks that he later sold for over $1 million.
You might assume Danny had simply ridden the tailwinds of AI’s surge in popularity. But two years later, he proved his entrepreneurship stripes yet again with HeadshotPro, an AI photo startup that earned over $100,000 just two weeks after launch.
Today, Danny is an accomplished founder, but as recently as 2019, he was just another digital nomad hustling to build his first startup in Bali. How did he achieve such explosive success in just a few years?
Spend Your Computer Time on Something Productive
Though Danny grew up in the Netherlands, his favorite childhood memory might be familiar. He begged his father for a Gameboy Color with Pokemon Silver. Finally, after a year of resistance, his father relented and brought one home for his birthday.
After this fateful day, Danny did what most kids his age do and played video games for hours. Both on the Gameboy and later the computer. One day, his father came home and threw a book on CSS at him.
“He said if I was going to be spending so much time on the computer, I might as well do something productive,” he says, laughing.
Programming was almost as thrilling as playing video games. Danny had started coding during the early days of the modern internet – a time full of possibilities and cheap web-building applications. He frequently built websites late into the night, feeling a sense of accomplishment he never felt at school.
“I hated school,” he says. “I cannot do things I dislike. I was always excited to go home and explore things I was interested in online.”
The late-night projects became profitable to young Danny when, at 15, his mother pitched him to her company to help them build their website. In return, he asked them to cover half the cost of a new MacBook Pro.
“It ended up being hundreds of hours of manually typed HTML, but it was nice to get that MacBook at the end,” Danny recalls.
The web-building experience started to pay off in other ways. Danny jumped into the online M&A world at 16 when he began selling his websites.
“I discovered sidedeals.nl, where people sold websites for a couple hundred dollars,” says Danny. “I decided to pick a category that does well and build something janky for it.”
Danny sold his hastily-built website for €125, which was significantly better than what he’d make in the same time working at the supermarket. He believes the experience opened his eyes to how lucrative building online could be. And how quickly he could capitalize on his work.
I transitioned from designing based on taste to designing based on what works
Danny persisted through his studies until he graduated in 2011. He later studied communications, multimedia design and UX, and media studies at the Hanze University of Applied Sciences Groningen.
In university, Danny’s relationship with learning improved significantly. He could connect what he was studying to a possible career. Especially instructive was one internship as a frontend designer and a conversion rate optimization specialist (CRO) at a business called Conversion Heroes. Here, he learned product design was more than just creating pretty things.
“I transitioned from designing based on taste to designing based on what works,” he says. “This is much more effective because you can literally go to clients and say, ‘Hey, I’m going to make this design because of this and this.’”
With his newfound design confidence, Danny won more jobs. His next gig in university – which he’d continue for years while building his SaaS projects – was designing ebook seller landing pages for $20 an hour.
One day, he summoned the courage, and against the advice of his friends, to ask for $75 an hour. He was fortunate that the landing pages had been selling well.
“The guy said, ‘That’s a lot of money, but we’ll do it.’”
Danny Goes to Bali
By the time Danny finished university in 2015, he was a reasonably accomplished web builder, designer, writer, and entrepreneur with a steady $75-per-hour job on the side. Now he needed to focus his many talents on a new project. He found it in Bali.
After a year of working in the Netherlands, Danny started backpacking across Asia in 2016. What started as a month-long break became a “10-month YOLO (you only live once) period.”
Danny says the trip transformed him from the shy kid bullied in school to the secure and unabashed man he is today. He also met Pieter Levels – founder of the popular digital nomad hub, Nomadlist, who also championed “the hardcore year” where he launched 12 startups in 12 months. Many Bootstrappers alumni cite Pieter as one of their primary influences.
He also began working at a coworking space called Tropical Nomads where he rubbed shoulders with others in the indie hackers movement like Jon Yongfook, James and Danielle from Leave Me Alone, famous Tailwind guy Erwin Langkeek, and a16z podcast host Steph Smith. Later he would help other up-and-coming indie hackers like Bootstrappers alumnus, Marc Louvion.
Much of this first group were members of a collective called Hackagu, a group meeting weekly to present what they were working on and receive critiques and advice. A similar concept to Bootstrapper alumnus Charlie Ward’s Ramen Club.
Over the pandemic, all the tourists fled Bali, but a small group of hackers, many in Hackagu, stayed and launched an explosion of new tech products that would later make them famous. Danny worked alongside this group, and his two businesses, Headlime and HeadshotPro, were among the most successful.
Selling Headlime for Seven Figures
Danny built his first startup, Headlime, during 2020’s Covid lockdowns.
Initially, it was just a PDF with 200 headline formulas. He turned it into a software tool that automatically modified headlines based on a handful of formulas. Then he launched a lifetime subscription and made $60,000 in revenue in one week.
Faced with his first potentially viral application, Danny frantically looked for ways to expand his success. He heard OpenAI had just launched GPT3. Instead of looking at it as competition, he saw an opportunity.
While many entrepreneurs might have waited until GPT3 became public, Danny immediately emailed Greg Brockman, then the CEO of OpenAI, and asked if he could get early access. Greg accepted.
Seeing AI’s potential, Danny transitioned Headlime entirely to GPT3, promptly went viral, and then sold it when he received a seven-figure offer in February of 2021.
In just four short years in Bali, Danny had crossed the threshold from wannabe tech bro to successful tech entrepreneur. But he still wanted to ask more of life.
A Second Chance at Glory With HeadshotPro
After selling Headlime for seven figures, Danny messed around for most of 2021. He tried a couple of halfhearted projects, got married, bought a house in Bali, and moved in with his wife. He was having fun, but growing increasingly bored.
An idea had been eating at him over the previous year. Why were AI art tools like Dall-E only used to generate art and not more practical pursuits like social media profile pictures?
In 2022, he started working on a profile picture creator. It was built on newly-released open-source tech, Dream Booth and Stable Diffusion AI. His friend Pieter happened to be doing the same thing.
“I was on Telegram with Pieter and he said, ‘Hey, I’m going to build this social media avatar project.’ I was like, ‘Dude, I’m already building this.’ So we started building our projects at the same time, helping each other along the way.”
I don’t think portrait photo shoots will be necessary in the future. It’s all going to be online and it’s going to save you hundreds of dollars
With each other’s help, Pieter completed his project, PhotoAI, in 25 hours, and Danny launched in about 30.
Both projects went viral on Twitter and made over $100,000. However, Lensa, an app-based competitor, ate into their profits. Danny says Lensa dominated through successful influencer marketing, plus it was easier to find and download through Apple’s App Store.
Danny and Pieter realized they needed to build niche products with proprietary software to compete. Danny moved to a product called HeadshotPro that could create realistic photos similar to a photo shoot. An accomplished photographer, he has many opinions on the future of AI photography.
“Profile pictures are nice, avatars are nice, but what is the real use case of photo AI?” Danny says. “The real use case is making realistic photos. I hate photoshoots. The one time I did one, the person told me I looked awkward, and I paid three hundred dollars for it. I don’t think portrait photo shoots will be necessary in the future. It’s all going to be online and it’s going to save you hundreds of dollars.”
Danny created a proprietary AI learning model based on Stable Diffusion. By March, he launched his realistic photo generator on Twitter. Again, it exploded in popularity.
“We did six-figure sales in a week, and it hasn’t fallen in popularity at all. It’s only been scaling up,” he says.
Danny knew he had a winning product as soon as people clicked his website links on Twitter.
“You know a product will sell well when the Twitter-to-website conversion rate is higher than one percent,” he says. “If your conversion rate is lower than one percent, it’s a shitty product. HeadshotPro had an incredibly high conversion rate for us, so I knew it was a winner.”
Now Danny could prove beyond a doubt that his career was more than just one lucky break. As long as he kept asking for more in life, the world would answer in kind.
Want to Avoid Burnout? Hire a Team
Counter to some in the indie hacker movement, Danny’s biggest piece of advice to other entrepreneurs is to get comfortable building a team as soon as possible.
“I was so burnt out last year, I had to take a break for three months,” he says. “After that, I was comfortable hiring a team. It’s so much easier as an entrepreneur knowing you don’t have to do everything. I think it gives me more freedom.”
You want to stop trading time for money
Danny also thinks founders should strive to create automated businesses. You can then take breaks from grinding without hurting your business.
“You want to stop trading time for money,” he says. “I was off for three weeks this past December and everything kept running. Making a living without always working is such a mind-blowing thing to realize.”
The most important thing for entrepreneurs, according to Danny, is for them to stop putting a ceiling on what they can build or dream. Ask for more.
“If your businesses start scaling, there’s just no limit,” he says. “You have this mind-altering realization of what is possible. It lets you dream really big, which is amazing to me.”