New York Tech Week drew some of the youngest self-made female millionaires in the country to the streets of the city, and Hard Knocks Women went looking for them. What followed was a series of sidewalk conversations that stripped away the polished LinkedIn bios and got to the real mechanics: the failed companies, the social pressure to buy designer bags, the grief folded into a business model, the high school dropout who invested in Anthropic before most people knew how to spell it. Three women stopped and talked, and every one of them had something sharp to say.
The publicist who lied about her age
The first was a 23-year-old entertainment publicist who had built a high six-figure PR business representing actors, athletes, musicians, and founders from a standing start of minimum wage in less than a year. She did it, she said, not by climbing toward the CEOs but by treating the assistants around her with the same respect she would give anyone above her. Those former cubicle neighbors became the source of some of her biggest clients.
She admitted she used to lie about her age to be taken seriously, and when asked about the biggest financial lesson from making that kind of money so young, she did not lecture. She called out designer bags bought under social pressure from music industry executives trying to flex like their artists. ‘Don’t feel pressured,’ she said. ‘Find out what your goals are and save up.’
The duo who turned puppy yoga into an 8-million-dollar wellness brand
The second encounter stopped two women walking together, and both of them were millionaires. They co-founded Puppies Sphere, scaling what they describe as a wellness category they built from scratch: structured time with dogs for people who cannot commit to owning one. They launched in Toronto after going through depression, crediting their own dogs with saving their lives, then moved to New York when they saw no scalable version of the concept existed in the US market.
In 2026 they brought in 8 million dollars across 12 studios in North America, all bootstrapped from their first class, which they ran without paid advertising and found people lining up. One of them lost her sister to suicide three years ago and now employs family members inside the business, surrounded by puppies every day. They described their working relationship with a line that landed plainly: ‘We are like husband and wife and wife and a husband depending on who needs what at a certain time in day.’
Asked to name the single thing that got them from zero to 8 million, the answer was immediate: ‘Build an experience or product that is simple, sticky, and people are obsessed with it.’
The serial entrepreneur who dropped out and invested in Anthropic
The third woman was 28 and had made her first million at 24 after dropping out of high school in Australia, where she said young women starting real businesses rather than content channels was genuinely uncommon. She moved through real estate, crypto, and a recent investment in Anthropic, describing her approach as always leaning toward the riskier side while still in her early twenties.
She sourced her education through podcasting, sitting down with sharp minds and asking questions rather than talking about herself. On imposter syndrome, which she said she feels every day, her method was direct: ‘I just hype myself, and also I realize no one actually cares.’ On the AGI timeline, she cited the chief business officer of Google X, who said he expects artificial general intelligence to reshape everything CEOs currently do within the year, and urged any entrepreneur with a product to build distribution now. If she had to start from zero today, she said she would use AI agents to build not just an app but a community with real in-life backing.
One detail that did not come with a lesson attached
One of the Puppies Sphere founders mentioned Chicago as the next expansion market, while the other named San Francisco and Santa Monica as already strong. They disagreed on that, said it plainly, and moved on.
All three women, a publicist who built her book out of assistant networks, two founders who watched people call their 2-million-dollar business ‘cute,’ and a high school dropout who compounded her way to multi-seven figures, landed on roughly the same place from different directions: start before you are ready, keep it simple, and pay close attention to the people standing next to you.
