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I turned my side hustles into a 7-figure career. Here are the 14 tools that made it possible.

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I’m an entrepreneur, creator, and investor based in New York. In a typical week, I do a lot.

I host over a hundred events a year for more than 20,000 people across New York, San Francisco, and Austin. I publish writing and video content that generates millions of impressions a month across LinkedIn, X, TikTok, and email, to an audience of more than 200,000 followers.

I’ve angel invested in over 20 startups. I advise companies on B2B marketing and growth strategy. I run two companies: Fibe, an events and media company, and The Shortlist NYC, a hiring events series for early-stage startups.

Most people hear that list and assume I have a big team behind me. I don’t.

When I left Google and Meta to build my own thing, the income streams were mine to create, and so was the chaos. What made it manageable, and eventually scalable, wasn’t hustle. It was tools. Specifically: AI, and the systems I built around it.

Here’s what I use, and why.

Claude Code: my LLM operating system

I think about Claude Code the way someone else might think about a chief of staff.

Claude Code isn’t just a coding assistant. It’s my operating system. It knows the context of my businesses, it has access to my systems, and it can execute tasks without me setting everything up from scratch each time.

It connects to my Notion workspace through a Model Context Protocol integration, which means it can read, write, and organize my project management database automatically. It plugs into my Customer Relationship Management. It drafts content, stress-tests ideas, writes emails, builds automations, and handles the kind of thinking work that used to eat half my day.

Notion and Airtable: the database layer

Notion is where I think. Airtable is where I track.

I use Notion as the primary database for all my TikTok and LinkedIn content: scripts, drafts, calendars, and status tracking across everything that needs to ship.

Because it connects directly to Claude Code through the MCP, a lot of this is automated. Content gets categorized, scheduled, and organized without me manually updating rows.

Airtable handles contact data and forms. Any time someone registers for an event, applies to The Shortlist, or fills out a partnership inquiry, that data flows into Airtable. It’s the operational layer: more structured, more relational, better for the kind of data I need to query and act on.

Zo Computer: my second computer

I have a computer I’ve never physically touched. It lives in the cloud, and it runs while I sleep.

Zo is a personal AI cloud computer that lets you build automations, host apps, run scripts, and connect to your tools. I use it to run background monitoring, host lightweight custom tools, and automate tasks that used to require either an assistant or significant manual overhead. It gives users their own AI-powered server that can run automations, integrate with personal data, and spin up custom software on the fly.

As Sean Thielen said, Zo is “The most evolved version of Notion.”

Lovable: from idea to prototype in hours

For The Shortlist, I needed a piece of software that didn’t exist. Something that could take a pool of job candidates and intelligently match them with the right CEOs and hiring companies based on role, stage, and fit. I built it in Lovable.

Lovable is a tool for prototyping and building mini-apps, and it has changed how I think about what’s possible without a development team.

I’m not an engineer, but I can describe a problem, iterate on a solution, and ship something functional in hours. The matching software for The Shortlist would have taken months and a significant budget to commission. Instead, it took a weekend.

Granola: the memory layer

The biggest tax on running multiple businesses is cognitive overhead. Every conversation, every deal, every commitment you make across a hundred events and 20-plus portfolio companies: if it’s not captured, it’s gone.

Granola is an AI note-taking app that automatically transcribes, summarizes, and analyzes meetings, then enhances the live notes by weaving in context from the transcript. I use it across every call I take. Sponsor conversations, investor check-ins, advisory sessions, and partnership negotiations; All of it is summarized, searchable, and ready for follow-up.

The follow-up email feature is what I use most. After a meeting ends, Granola has enough context to draft an accurate, personalized follow-up in seconds.

Wispr Flow: I speak more than I type

I have a microphone on my desk. I speak to my computer more than I type. In fact, I’m speaking to my computer right now as I write this.

Wispr Flow is the voice-to-text tool that works across every application, four times as fast as typing, with AI commands and auto-edits built in. I use it to draft emails, LinkedIn posts, newsletter sections, and partnership briefs.

My first drafts are almost entirely spoken now. The friction of writing dropped dramatically once I stopped treating my keyboard as the only input.

Kondo: Superhuman for LinkedIn

Most of my business happens in two places: LinkedIn and text messages.

LinkedIn is where brand partnerships come in, where potential sponsors for Fibe reach out, where founders apply to The Shortlist, and where my content builds the relationships that turn into revenue.

Kondo is often called “Superhuman for LinkedIn.” It helps professionals who rely on LinkedIn for business development, recruiting, and networking manage high volumes of messages without missing important opportunities.

I can label conversations, snooze follow-ups, use keyboard shortcuts to process messages in bulk, and keep my inbox at zero. It’s the single biggest workflow upgrade I made this year.

Raycast: the command layer

When multitasking across multiple businesses and revenue streams, the cost of context-switching adds up fast. Every time I reach for my mouse, hunt for an app, or retype something I’ve written before, that’s friction. Friction compounds.

Raycast is a keyboard-first launcher that gives users fast access to applications, text snippets, clipboard history, scripts, window management, and more, all from a single shortcut.

I use it to jump between tools without touching my mouse, insert saved text blocks for messages I send repeatedly, launch automations, and run commands across the apps I use most. There’s an AI layer built in now, too, which means I can trigger Claude from anywhere on my screen without switching context.

Substack and beehiiv: the newsletter layer

I run two newsletters for two different audiences, so I use two different platforms.

Substack is my personal blog and newsletter. It’s where I write about entrepreneurship, events, sobriety, and the things I’m thinking about. The writing environment is clean, the subscriber relationship is direct, and the community Substack has built around serious writers makes it the right home for work I actually care about.

Beehiiv powers The Shortlist’s newsletter, the one that goes to founders, operators, and startup hiring teams. Beehiiv is built differently, more growth-oriented, better analytics, and more infrastructure for a publication that’s part of a business.

The two platforms serve two different purposes, and I wouldn’t swap them.

Framer: building brands, not just websites

Most of my websites are built on Framer, but it’s more than a website builder.

Framer is a design-first web platform that lets you build sites that actually look the way you want them to, without compromising on performance or having to manage a developer relationship for every update.

My event pages, my company sites, my personal brand presence: all Framer. It’s also fast enough that I can update a landing page for an event the night before it happens, without waiting on anyone.

Endel and Othership: the operating state

None of the tools above matter if your operating state is off.

I use Endel for deep work. It generates adaptive soundscapes calibrated to focus, sleep, and recovery. When I’m writing, building, or working through a complex problem, Endel is running in the background. It keeps me in the zone in a way that playlists and lo-fi beats simply don’t.

Othership is how I wind down. It’s a guided breathwork and meditation app that I’ve invested in and use at the end of the day to decompress.

In a work life that doesn’t have clear boundaries because you’re always the founder, the content creator, and the investor simultaneously, having a deliberate off-ramp is not a luxury. It’s maintenance.

Andrew Yeung is a former Meta and Google employee who now produces tech events through Fibe, runs The Shortlist NYC hiring series for early-stage startups, and invests at Next Wave NYC.




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Avoid these 3 mistakes after a layoff, career coach says

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A storm of layoffs is upon us.

More than 1.1 million people were laid off in the US in 2025, and there were more job cuts in January 2026 than any January since 2009, according to reports. Business leaders are predicting that things will only get worse as AI disrupts the workforce.

When Amazon announced layoffs earlier this year, the tech career coach Kyle Elliott shared what he thinks employees should do immediately after being laid off to put them in the best position to find a new role.

He also shared three common mistakes to avoid after a layoff.

1. Posting a hit piece on LinkedIn

After the sting of a layoff, Elliott has seen workers turn to LinkedIn to share negative posts about their former employer.

“Sometimes people just really react from that emotion or wound, instead of waiting until it heals,” he said.

Such posts could be detrimental when applying for a new job, when recruiters and hiring managers check your LinkedIn profile.

“People want to work with other positive people, so if they see that you’re venting, they may worry, ‘if we have to conduct layoffs in the future, are you going to then put a hit piece out on us as soon as you get laid off?” Elliott said.

Instead, consider waiting until you are more able to position the event differently in your post, which could be a month or two after, Elliot said. In the post, share lessons you learned and the amazing work you did at your previous company, he added.

2. Venting to former colleagues

Former colleagues can be a good resource when you’re looking for jobs in the future. In your last conversation with your former colleagues before leaving the company, reiterate the work you’re proud of and share what kind of opportunity you’re looking for next, Elliott said.

With this in mind, it may be better to vent about your layoff experience to a trusted confidant like a spouse, best friend, or therapist rather than a former colleague, he added.

Venting to a colleague could damage their perception of you and jeopardize the connection.

“A lot of people will remember that last piece, and you don’t want them to be like, ‘oh, they’re bitter.'” he said.

3. Being afraid to network

Elliott has noticed that clients are sometimes afraid to network because of the stigma associated with layoffs, and their fear that they can’t add value to conversations while unemployed.

“Layoffs are normal now,” Elliott said, so there’s no need to avoid reaching out to people out of fear.

He recommended starting small. For example, meet a former colleague whom you were close to.

In your first conversation, focus on putting yourself out there and taking small steps toward your next role, and don’t expect to be offered a job, he said.

“If you were fired and you’re calling it a layoff, it’s a little different. But if you were truly just laid off as part of a reorganization or cost-cutting measures, people understand that, and there shouldn’t be shame in that,” he said.




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Career tips for creators from 5 of Steve Jobs’ powerful friends on what would have been his 71st birthday

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Late Apple cofounder Steve Jobs had a variety of powerful friends, and they’re honoring his legacy by sharing their recipes for success.

To celebrate his birthday on Tuesday, the Steve Jobs Archive released two collections of letters from business leaders, designers, writers, and more.

The entries were originally distributed to 2023 and 2024 fellows of the SJA program for young creators, and they’ve been compiled into two volumes titled “Letters to a Young Creator.”

The volumes feature the words of advice from tech trailblazers like Tim Cook and Jony Ive, to successful businessmen Bob Iger and Arthur Rock, to creative minds like Pixar’s Pete Docter and filmmaker Jon Chu.

Some wove their lessons together with personal anecdotes about their relationships with Jobs, while others laid out lists to aid in the creative process.

Tuesday would’ve been Jobs’ 71st birthday. The former Apple CEO died in 2011 after living with pancreatic cancer for a number of years. Jobs became known for his inspirational public speeches and quotes shared by those who worked closely with him.

Volume one of “Letters To a Young Creator” ends with an email Jobs sent to himself in 2010. In the note, he reflected on how his appreciation for human creativity.

“I love and admire my species, living and dead, and am totally dependent on them for my life and well being,” Jobs wrote.

In volume two, Jobs referred to himself in a 1984 quote as a student.

“Don’t take it all too seriously,” he concluded.

Here’s what his friends had to say about pursuing success as a young creator.

Tim Cook posed one question to young creators


Apple CEO Tim Cook

Apple CEO Tim Cook took over for Jobs in 2011.

Perry Knotts/Getty Images



Cook took over as CEO in 2011 after Jobs stepped down to focus on his health. Before his death, the pair worked closely together at Apple. Cook has been with the company since he met Jobs in 1998.

In his 2024 letter, Cook described the fateful meeting that led to a decadeslong career at one of the biggest tech companies in the world. He said he was warned against taking a job at Apple as the company had been struggling around that time. One conversation with Jobs changed everything.

“I had never met someone with so much passion and vision,” Cook wrote. “I knew I had to be a part of it.”

His advice to young creators facing similar decisions on their future career paths was to ask themselves one question.

“And so when you imagine your future, and the winding path that is laid before you, remember the question you should ask is not ‘What will happen?’ but ‘Who will I be when it does?'” Cook said.

Jony Ive said that Jobs liked to focus on ideas


Former chief design officer of Apple Jony Ive

Former chief design officer of Apple Jony Ive worked closely with Jobs.

Mike Windle/Getty Images



Ive, Apple’s former design chief, worked with Jobs for nearly 15 years. The pair would often have lunch together as they came up with ideas that led to successful products like the iPhone.

Ive wrote about his relationship with Jobs.

“His insatiable curiosity was not limited or distracted by his knowledge or expertise, nor was it casual or passive,” Ive wrote. “It was ferocious, energetic, and restless.”

Ive and Jobs connected over their shared curiosity. He encouraged people to be like Jobs and show their admiration for humans by being creators themselves. According to Ive, Jobs was focused on ideas rather than the problems that come along with them.

“Ideas are fragile. If they were resolved, they would not be ideas, they would be products. It takes determined effort not to be consumed by the problems of a new idea,” Ive wrote.

Pete Docter listed tips that help his creative process along


Pixar's Pete Docter

Pete Docter directed several Pixar movies.

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Docter is the chief creative officer at Pixar, which Jobs owned before Apple’s comeback. In recent years, Docter has been vocal about the intersection of tech and animation, saying artificial intelligence won’t fully replace humans in filmmaking.

He’s known for directing hit animated movies like “Monsters, Inc.,” “Up,” “Inside Out,” and “Soul.”

Docter laid out nine tips that he uses in his own creative process. Here are three of them:

  1. Start with whatever shows up. Go as far as you can on that initial confidence and enthusiasm.
  2. Start fast and rough; worry about details later.
  3. Each day, start by pretending you’ve never seen it before, with no expectations or preconceptions. Take it in as your audience will: see what it is, not what you HOPE it is. Then change or add to make it better.

Bob Iger said to take risks


GREEN BAY, WISCONSIN - NOVEMBER 10: Walt Disney Company CEO Bob Iger looks on prior to the game between the Philadelphia Eagles and the Green Bay Packers at Lambeau Field on November 10, 2025 in Green Bay, Wisconsin. (Photo by Michael Reaves/Getty Images)

Disney CEO Bob Iger led the acquisition of Pixar in 2006.

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Iger has had two stints as Disney’s CEO, starting in 2005. The media giant acquired Pixar in 2006. Jobs became a member of Disney’s board of directors as part of the deal.

In true Disney fashion, Iger wrote about “magic and wonder” in his letter to creators. He remarked that creativity can’t be reduced to math or science.

Being risk-averse, he said, is the “death of creativity.”

“Second-guessing creative decisions is a perilous endeavor. Learn from creative mistakes, and never second-guess why things were made,” Iger wrote. “Instead, ask how they could have been made better.”

Arthur Rock said it’s all about who you keep around

Rock is an iconic Silicon Valley investor behind Intel, Xerox, and Apple. The 99-year-old wrote his 2025 letter about what makes a good leader.

“A good leader chooses good people,” he said.

Execution outweighs ideas, according to Rock, and finding people who can execute is essential. It’s the traits that money can’t buy, like “fire in the belly,” that Rock learned to identify throughout his decades as a venture capitalist.

“You want people who know what they can do, and do it. Even more important: You want people who know what they don’t know,” Rock said.




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I hosted a $30 vision workshop to reset my life and career. Here’s how I did it in 3 steps.

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The Year of the Fire Horse

A dozen or so friends clamoured around my fireplace’s mantel to grab their Dollar Store-bought journals and select a fancy gel pen. A ChatGPT-designed workshop on creating a 2026 vision for one’s life was about to begin, and two of my friends were fighting over who would get the last brown leather-bound journal.

It was a little before Lunar New Year, a holiday rooted in honoring the past while setting intentions for the future. And this year, instead of enjoying fireworks and celebrations, I hosted something much quieter. I invited my circle into my home to answer several journal prompts around career, love, fitness, and finances.

For me, January 1 comes with too much pressure; you may remember me writing about my intentionally slow start to the New Year. Lunar New Year, however, gifted me a second chance at intention. And what resulted around my dining room table was the perfect anecdote to help me game-plan my goals. By the end of the party, we walked away with clarity and focus, and identified the gaps standing in our way.

If you want to recreate this moment, here are three tips to create an atmosphere designed for reflection.

  1. First things first, here was my prompt into ChatGPT: What are some good prompts for self-reflection? I want to create a vision workshop that sets goals on faith, finances, work, love, family, and life. Can you create the interactive workshop?
  1. Then, we laid ground rules: Yes, I encouraged my friends to share the goals they had scribbled down, but I also encouraged them to keep some answers close to the vest, as some goals thrive in incubation.
  2. Lastly, I prioritized making my friends feel comfortable. There were candles lit everywhere, a basket of cheap yet cozy socks so they could kick their shoes off and relax, and don’t forget the fancy gel pens to make the journaling experience feel whimsical.

I still don’t know what 2026 will bring, but instead of creating rushed, vague resolutions, at least I had a moment to be reminded that life moves in cycles, and ambition requires vision.




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How Savannah Guthrie’s mom has helped shape the ‘Today’ anchor’s career

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In a 2019 graduation speech at George Washington University, she said leaving law was “one of the biggest, craziest jumps” she ever made.

“It wasn’t a cliff; it was the federal courthouse here in Washington, DC,” she said.

Months before she was due to start as a law clerk for a federal judge, she had an epiphany.

“It wasn’t my dream,” she said. “What I really wanted was to go back to my roots in journalism. I still had that nagging hope that one day I could really make it in television news.”

Guthrie spoke with the judge. He asked why she didn’t come work for him for a year, since it would help her career, especially since she didn’t have a job lined up.

“And that’s when I looked at him and told him: ‘I know you’re right. What you say makes perfect sense,'” she said. “‘But I also know myself, and if I don’t do this, right this minute, I will never have the guts again.'”

From 2004 to 2006, she was Court TV’s legal-affairs correspondent.

She covered cases like the Zacarias Moussaoui trial, the Boston clergy sex-abuse scandal, and the Scooter Libby case.




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Catherine O’Hara has died at 71. See her career in photos.

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  • Comedy legend Catherine O’Hara has died at 71.
  • O’Hara was known for her many roles, including Schitt’s Creek,” “Home Alone,” and “Beetlejuice.
  • Her final public appearance was at the Emmys last year.

Catherine O’Hara, two-time Emmy Award winner and beloved movie star, has died at the age of 71.

A representative for O’Hara confirmed the news to Business Insider on Friday afternoon. Her agency said in a statement that her death on Friday came after a “brief illness,” per The Associated Press.

O’Hara has been a fixture of TV and movies since breaking out on the Canadian sketch comedy series “SCTV” in the early ’80s alongside John Candy, Eugene Levy, Martin Short, Andrea Martin, and Rick Moranis.

Since then, she’s become beloved to audiences for her roles in
“Beetlejuice,” “Home Alone,” “Schitt’s Creek,” “The Studio,” “Best in Show,” “The Last of Us,” and many voiceover roles, including Sally in “The Nightmare Before Christmas” and Susan Frankenstein in “Frankenweenie.”

See her legendary career in photos.

Catherine O’Hara’s breakout was performing with the Canadian comedy troupe Second City in the ’70s and ’80s.

Catherine O’Hara during a taping of “SCTV.”

Reg Innell/Toronto Star/Getty Images

“SCTV,” a sketch series about a fictional TV network, ran on Canadian television from 1976 to 1984 and on NBC from 1981 to 1983.

O’Hara was just one of the many Canadian comedians who were introduced to American audiences through “SCTV,” which was something of a cult classic.

She won her first Emmy, for writing on “SCTV,” in 1982.

She met many of her longtime collaborators there, including Eugene Levy.


John Candy, Catherine O'Hara, Andrea Martin, and Eugene Levy.

John Candy, Catherine O’Hara, Andrea Martin, and Eugene Levy.

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“You’re lucky to work with friends, and I think it’s nice to see friends together. I like knowing when people know each other and have a history; that comes across on screen. I think it’s fun for people to see. It is for me,” O’Hara told BuzzFeed about working with Levy in 2014.

Her first major film role was 1988’s “Beetlejuice,” sparking another long collaboration between O’Hara and director Tim Burton.


catherine o'hara in beetlejuice

O’Hara in “Beetlejuice.”

Warner Bros.

The “Day-O” scene in “Beetlejuice” is perhaps the most iconic in a film filled with iconic scenes, and it all starts with O’Hara’s character.

O’Hara went on to work with Burton in “The Nightmare Before Christmas,” “Frankenweenie,” and “Beetlejuice Beetlejuice.”

“Beetlejuice” was also important for her personal life — she met her husband, production designer Bo Welch, on the set.


bo welch and catherine o'hara in 1989

Welch and O’Hara in 1989.

Ron Galella, Ltd./Ron Galella Collection/Getty Images

They were married from 1992 until her death. They shared two sons.

O’Hara will always be known for playing Kate McAllister in 1990’s “Home Alone” and its 1992 sequel.


catherine o'hara in home alone

O’Hara in “Home Alone.”

20th Century Fox

O’Hara has been a staple in homes around the world every December for 35 years due to her role as Kevin’s mom, Kate, in “Home Alone” and “Home Alone 2: Lost in New York.”

She also appeared in multiple mockumentaries written and directed by Christopher Guest in the ’90s and 2000s.


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Levy and O’Hara in “Best in Show.”

Warner Bros. Pictures

Specifically, she was in “Waiting for Guffman” in 1996, “Best in Show” in 2000, “A Mighty Wind” in 2003, and “For Your Consideration” in 2006.

Starting in 2015, she became known to an entirely new generation as Moira Rose in “Schitt’s Creek.”


cast of schitts creek

The cast of “Schitt’s Creek.”

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“Schitt’s Creek” became a full-blown phenomenon across its run from 2015 to 2020, and many of the show’s most memorable moments came from her character, Moira.

She won an Emmy for her performance as the lovably kooky Rose matriarch.


catherine o'hara with her emmy

O’Hara with her Emmy Award.

Frank Ockenfels/ABC/Getty Images

She won in 2020 after receiving a nomination for the prior year, as well. It was her second win from eight nominations.

Her last public appearance was the 2025 Emmys, where she was nominated for her performances in “The Last of Us” and “The Studio.”


catherine o'hara at the 2025 emmys

Bo Welch and O’Hara at the 2025 Emmys.

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O’Hara was a double nominee at last year’s Emmys: she was nominated for outstanding supporting actress in a comedy series for “The Studio” and outstanding guest actress in a drama series for “The Last of Us.”




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Karoline Leavitt called her age-gap marriage an ‘atypical love story.’ Here’s what to know about her life and career.

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Leavitt was introduced to Riccio, a real-estate developer, at a campaign event by a mutual friend during her 2022 run for Congress.

They announced their engagement on Christmas in 2023 and welcomed a son, Niko, on July 10, 2024.

Leavitt and Riccio wed on January 4, 2025, days before Trump’s second inauguration. Leavitt spoke about their 32-year age gap in a February 2025 interview on The Megyn Kelly Show.

“I mean, it’s a very atypical love story, but he’s incredible,” she said of Riccio, adding, “He’s the father of my child, and he’s the best dad I could ever ask for. And he is so supportive, especially during a very chaotic period of life.”

In a November interview with Miranda Devine on the podcast “Pod Force One,” Leavitt spoke about her parents’ reaction to her “unusual” relationship with Riccio, who is older than her mother.

“It’s definitely a challenging conversation to have at first,” she said. “But then, of course, once they got to know him and saw who he is as a man and his character and how much he adores me, I think it became quite easy for them.”

On December 26, Leavitt announced that she and Riccio are expecting a baby girl in May, making her the first-ever pregnant White House press secretary.

“My husband and I are thrilled to grow our family and can’t wait to watch our son become a big brother,” she wrote in an Instagram post.




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A Facebook veteran took a big career risk that resulted in a ‘giant failure’ — but embracing a ‘J-curve’ career path paid off

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At 25 years old, Molly Graham was thriving in Facebook’s HR department when a senior executive urged her to transfer out of her stable role and help build a mobile phone instead.

She took the risk — and it could have derailed her career.

But Graham, who later became a C-suite executive at some of America’s biggest companies and philanthropies, now views that risky bet as one of the most important moves she ever made.

“It just felt like falling off a cliff,” Graham, now the founder of Glue Club, said in a recent interview on Lenny Rachitsky’s podcast. “Taking risks, accepting the terrible fall and that experience of falling has been more than worth it.”

Graham described the experience as part of what she calls the “J-curve” — a career trajectory where a risky move leads to an initial drop before eventually producing outsized gains. Visually, she describes it as standing on a ledge, stepping off, sinking briefly, and then rising far higher than where you started — just like the shape of the letter J.

The concept, which she has also written about in her Lessons Substack, challenges the idea of a steady career ladder that steadily moves up and to the right.

Instead of climbing rung by rung with promotions every two to five years, Graham argues that some of the most valuable professional growth comes from jumping into roles you aren’t ready for and surviving any setbacks.

Graham’s own J-curve began when billionaire investor and “All-in” podcast host Chamath Palihapitiya, then Facebook’s vice president of growth, recruited her to help develop a smartphone, encouraging her to make the move by sketching out the J-shaped trajectory on a whiteboard.

He brought her on despite her having no experience in product development, dropping her into rooms filled with engineers and phone specialists with deep subject matter expertise. She recalled feeling like an “idiot” for much of her first six months.


Headshot of Molly Graham, the former Facebook and Google executive, and writer of the Lessons Substack

Molly Graham, the former Facebook and Google executive and writer of the Lessons Substack.

Molly Graham



At her midyear review, Palihapitiya delivered what Graham called the worst performance evaluation she had ever received. But the new experience eventually expanded her expertise.

“Slowly, I remember I had been doing all these trips to Taiwan because we were actually working on hardware and I, at some point, came back from Taiwan and I like drew on a whiteboard for him the layout of a mobile phone, trying to explain to him kind of like why something he wanted to do was not possible,” Graham said. “And I so vividly remember walking out of that meeting being like, ‘Oh like I actually know things.’ And slowly then over the following three years I became an expert in mobile.”

Palihapitiya did not respond to Business Insider’s request for comment.

“The phone itself was a giant failure — a massive, costly failure for Facebook,” Graham told Rachitsky on the podcast. “But it was not a failure for me.”

She credits the experience with teaching her that she could operate far outside her comfort zone — a lesson that later helped her take on senior leadership roles, including serving as COO of Quip, which Salesforce acquired for $750 million, and overseeing operations at the $7.4 billion Chan Zuckerberg Initiative.

The J-curve, Graham said, is especially common at fast-moving companies like Meta, Alphabet, Nvidia, and SpaceX, where leaders value employees who are willing to take big risks early and learn quickly. In those environments, proving adaptability can matter more than checking every qualification box.

Not everyone supported Graham’s decision at the time. She said Facebook COO Sheryl Sandberg, then the number two at the tech giant, advised against the move — as did her father.

“When wiser, more experienced people questioned the job offer, it definitely made me pause,” Graham told Business Insider in a follow-up email. “But my gut felt really strongly that I needed to take the risk.”

That instinct, she said, ultimately helped her discover what kind of work she didn’t want to do, and where her strengths lay. She didn’t want to sift through mock ups of hardware design and argue about a button’s placement. Instead, she sharpened her management skills and prepared to help lead large organizations.

“The much more fun careers are like jumping off cliffs,” Graham told Rachitsky. “They can take you to places that you never could have imagined.”




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Americans are living in a ‘career industrial complex.’ Venture capitalist Bill Gurley explains how to break out and find your dream job.

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A top Silicon Valley investor has an antidote for “quiet quitting.”

Bill Gurley is a general partner at venture capitalist firm Benchmark and the author of “Runnin’ Down a Dream, How to Thrive in a Career You Actually Love.” Gurley told Neal Freyman and Toby Howell on the “Morning Brew Daily” podcast that aired on Sunday that it is “horrific” how some people are actively disengaged at work, but the heart of the matter is that people “aren’t ending up in the right place.”

“We developed this mindset where you push kids toward economic safety — doctors, lawyers, jobs where unemployment is low, and salaries are high,” said Gurley. “But we’ve pushed a lot of kids into what I call the ‘career industrial complex.'”

Gurley said that the “career industrial complex” means pushing children toward a “résumé arms race” of standardization and credential accumulation, rather than encouraging curiosity and exploration.

A simple test as to whether you would be successful in your dream job, said Gurley, is whether you would be willing to learn on your own time.

“I like to say, you know, if you have three episodes of Breaking Bad left, would you study this instead?” said Gurley. “Like, does it compete with what you do in your free time?”

Gurley added that he once did a survey where he asked 10,000 people if they would choose a different career if given the chance to go back in time, and 60% said yes.

Gurley’s comments came as workplace trends such as “job hugging” and “quiet cracking” emerged in 2025.

While workers feared layoffs and the prospects of landing new roles dimmed for many young professionals.

A Gallup poll done in 2024 found that employee engagement in the US fell to its lowest level in a decade, with only 31% of employees feeling engaged. Additionally, workers under the age of 35 are less engaged compared to other age groups.




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