Regina Jaslow

The through-line

Regina Jaslow's recurring argument is that risk is smaller than it feels, and that the only sane way to live and build is to treat everything as an experiment. She describes herself as a sensitive, timid child who avoided attempting things because failing would make her unhappy, until she worked out the actual downside: "if I said something that wasn't right or if I did something that wasn't right or I asked somebody to give me something that they didn't want to give me what's the worst that could happen they would just say no and nothing would change" [1]. That realisation, she says, "suddenly opened the doors for me" [1]. The companion idea is ruthless triage of worry: deciding what is inside your control, acting on it, and putting the rest down. Both habits are presented as learned rather than innate, which is why she frames them as advice rather than temperament.

The second through-line is the business one: helping organisations that find technology daunting actually adopt it and get returns from it, whether that is AI adoption and maximising ROI on AI investments at Innocuous AI [1], or breaking down complex barriers at the intersection of technology and healthcare in her earlier work at Amplicare [2].

On treating life as a series of experiments

The framing comes from a science class and she applies it literally. "In science everything is an experiment right you do petri dish number one petri dish number two you just keep going it does it's not failure it's like you're trying to undiscover every variable and change one variable one variable so that you can't isolate right so in life life is just one series of experiments and that's all there is to it" [1]. She extends this to a genuinely deflationary view of achievement: "I think the perception of failure and success is is relatively arbitrary" [1]. On her account, some people experiment and get "a good result early on and they were lucky in some ways," while others are unlucky and it "takes many many more experiments to get there," and that difference is the journey rather than a verdict on the person [1]. The practical consequence is that a bad outcome closes a loop instead of opening a rumination: "I gave it a whirl I gave it a try it didn't work out so be it moving on you know next experiment" [1]. She applies the label to her own history without exception, calling a mis-pitched college application "experiment number one went awry" [1].

On controlling what you can control

She is direct about the mental discipline that keeps the highs and lows of a startup from becoming paralysing. Of the people who cannot sleep because "the record player is playing ahead constantly," she says the antidote is "the power to be able to just say I'm done with that you know there's nothing I can do now I'm going to go to sleep and just put it away" [1]. Her test is the boundary of agency: when a situation "is something I really can't control or I can only control to a certain extent and I've done what I could," then "whatever happens happens" and she lets it go [1]. She sums up the operating rule as focusing "on what I have the power to take action on and everything else I just let it be," and credits it with getting her past difficult situations without being bogged down [1]. She also traces the origin honestly: as a child she cried over everything, and her mother told her to "toughen up and just you know build an armor and and be stronger," advice that stuck [1]. Asked whether she was always this level-headed, her answer was that as a student she was "probably lost and confused like everybody else" [1].

On persistence after rejection

Her Wharton story is told as a lesson in not accepting other people's verdicts. Rejected the first time, she went to the University of Michigan, did well, and then grew suspicious of her own results: "my grades were too good I'm not that smart and I was like there's something wrong with this picture" [1]. Rather than speculate, she flew to Philadelphia and sat in on classes to test the environment for herself, concluding "this is indeed the place for me" [1]. She also diagnosed the original failure specifically instead of globally: as an international student who had never been to the country, she had written an essay imagining what an American admissions counsellor wanted and "did not understand the American psyche whatsoever," so she rewrote it and transferred in [1]. The lesson she draws is explicit: "don't um despair or give up if you believe it's where you belong," and "if you believe you're good enough you can make it so if you try again" [1].

On zero-sum thinking and who you keep around you

She found the undergraduate environment cutthroat, with grading on a curve producing the mindset that "if I help you then um I'm helping my competitor in in the score curve" [1]. Her response was selective rather than confrontational: she joined student groups, made friends she still cherishes, and deliberately distanced herself from people whose mindset she describes as "slightly toxic or on their way there" [1]. The underlying belief is economic as much as social: "life is not exactly a zero-sum game you can widen the pie for everybody," and she treats being surrounded by people who hold that view as an important thing to engineer for [1].

On adapting as an outsider

Fitting in, in her telling, was another experiment with a deliberate change in strategy. As a Singaporean at Michigan with a British-style accent, every party turned into the same exchange, "where are you from," followed by a geography lesson because people thought Singapore was in China or could not place it on a map, and surprise that English was her first language [1]. After a year of this she simply wanted "normal conversation with normal conversation," so she set out to learn the American accent by studying American shows and the vocabulary that went with it, saying "plant" one way rather than another and "the trunk of the car instead of the boot" [1]. She is careful about the motive: people did not treat her poorly, but the difference "called me out as a person who didn't quite fit in" [1].

On evaluating opportunities by their downside

Her career advice inverts the usual due diligence. Rather than collecting other people's success stories, she recommends learning about their difficult experiences, and choosing work whose hard parts you can tolerate rather than work that only looks good at its best [1]. It is the same calculation she applies to risk generally: understand the realistic worst case, and decide whether you can live in it.

On building through a year of extremes

She describes 2022 as a run of alternating highs and lows: the first user on the platform, then her co-founder being stabbed while travelling in Brazil and injuring his vocal cords so badly he could not speak, then the first VC investment, then her father's death [1]. What she emphasises about the low points is improvisation rather than pausing. With customer calls already booked and a co-founder who could not talk, "he would chat you know WhatsApp to me and then I would speak on his behalf," including technical conversations [1]. She calls the whole year eventful and memorable and says she was looking forward to what came next [1].

On making AI and technology usable for ordinary businesses

The commercial thesis behind Innocuous AI is that adoption, not capability, is the bottleneck. She is focused on helping firms use artificial intelligence to enhance their business and serve customers better, and on helping organisations navigate their AI journey so they can maximise the return on their AI investments faster [1]. That interest in translating hard technology into usable value predates the AI company: at Amplicare she worked on breaking down complex barriers at the intersection of technology and healthcare [2]. Her earlier startup, Dovetree Style, was bootstrapped to cash flow positive quickly and sold as a multi-branded business in 2019 [1].

Takeaways

• Test the real downside before deciding not to act: in most cases someone says no "and nothing would change," which she says is what finally opened doors for her [1].
• Treat outcomes as experiments rather than verdicts, changing one variable at a time, because "the perception of failure and success is is relatively arbitrary" [1].
• Draw a hard line at the edge of your agency: act on what you can control, then "just say I'm done with that" and put the rest down so it does not keep you awake [1].
• A rejection is a diagnosable failure, not a judgement. She identified the specific flaw in her first Wharton essay, reapplied and transferred in, and advises against giving up "if you believe it's where you belong" [1].
• Avoid zero-sum environments and the people who thrive in them, on the view that "you can widen the pie for everybody" [1].
• When evaluating a job or venture, ask people about their hardest experiences rather than their successes, and pick work whose difficult parts you can actually tolerate [1].
• Ship around obstacles rather than pausing: with a co-founder unable to speak, she ran customer and technical calls while he fed her lines over WhatsApp [1].
• The problem worth solving in AI is adoption and ROI, helping organisations navigate their AI journey so investments pay back faster [1].