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Jenny Stojkovic

Jenny Stojkovic

@jenniferstojkovic

venture capitalist, tech content creator w/ 250K+ followers, keynote speaker, & former silicon valley lobbyist (meta, google, microsoft)... also a bestselling author, rescue diver, & boy mom

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Posts

Jenny Stojkovic

Entrepreneurship

2mo

honestly, I know when something is about to blow up, and this is one of those things... looking for a brand partner to help bring the next events in The Women Creators series come to life. our first event was a massive success with hundreds of people joining for the waitlist for this month's event... we've got a full series already locked in Venice at The Lighthouse until the summer w/ top CEOs, experts, & founders... and we might even be taking this thing bi-coastal to NY! 👀 this is not a drill. if your brand wants to get in front of 100+ women leaders in the creator economy + reach 200K followers across social, send me a message!!
117

Jenny Stojkovic

Entrepreneurship

2mo

This 42 year old CEO was born to refugees who escaped Vietnam on a sinking boat. Then, she sold her company for $875 million. Meet Tracy Young, Founder and CEO of TigerEye. Tracy grew up in Milpitas, California. Her parents were Chinese-Vietnamese refugees who fled the Vietnam War in 1977. They were on a fishing boat for 8 days with 300 refugees. Starving. No coast guard wanted to pick them up. They bribed an oil rig to sink their boat so they'd be rescued. They made it to California through a priest and worked multiple jobs. Her dad drove a taxi. Her mom worked swing shifts building ships. Eventually, they built a wholesale food distribution business and put all three kids through college. Tracy became a construction engineer. One day, she had to check 800 rooms in a hospital. She lugged 50 pounds of paper blueprints around in a cart. She ordered 15 extra sets of blueprints for one meeting. The bill? $27,000. That night, she went for drinks with her college friend. He'd just bought the first iPad. He slammed the table and said: "This is ridiculous. All of this should be on this iPad." That was the start of PlanGrid. In 2011, Tracy and her co-founders started building the company. One of her co-founders, Antoine, was diagnosed with a rare form of cancer right before they applied to Y Combinator. He passed away in January 2012. Before he died, he told Tracy: "Life is short. Take care of the ones you love. Don't be afraid to try new things. Never do anything that makes you unhappy." They got into Y Combinator. She kept building. Tracy sold most of PlanGrid on her own -- up to $5 million in revenue. She personally called every lead. When they couldn't afford conference booths, they ran demos in the hallway. Two of their top 10 customers came from those early hustle days. By 2018, PlanGrid had 500 employees. Over 1 million construction projects in 195 countries. $100 million in annual recurring revenue. Autodesk acquired PlanGrid for $875 million. When investors used to direct questions to her male co-founders instead of her, she responded by sponsoring conferences for women in construction and mentoring female entrepreneurs. In 2022, she started her second company, TigerEye, with her husband. They raised $35 million. "I am truly starting this company as an activist. If the world needs another company led by a woman, here I am. My parents were refugees of war. They didn't get to choose what they worked on. But I get to." What makes Tracy remarkable is that she didn't just build a tech company. She built it in construction, one of the least tech-forward industries on earth, while being a woman in a field that is 97% male. Tracy may be one of the most successful female founders in tech history, yet this post might be the first time you've ever heard of her. That's why I share the stories of women execs and founders like Tracy every Wednesday for #WomenFounderWednesday. 🔔 Subscribe to Jenny Stojkovic for more.
1.3K

Jenny Stojkovic

Entrepreneurship

2mo

The layoff numbers are staggering. Meta laid off hundreds of employees yesterday. Block just cut nearly half its workforce — with Jack Dorsey saying AI made it possible to run the company with a “significantly smaller team.” Oracle may slash up to 30,000 positions to fund AI data centers. Intel, UPS, Accenture, Verizon — tens of thousands of jobs each. And most people walking into those conversations have no idea how much leverage they actually have. Here’s what I wish more people knew: → If you’re 40+, federal law requires at least 21 days to review a severance agreement. If they rushed you, that waiver may not be enforceable. → Severance is almost never take-it-or-leave-it. You can negotiate pay, benefits, equity, even removing your non-compete. → If 50+ employees were laid off without 60 days notice, look into the WARN Act. You may be owed back pay. → Get your reference language in writing. Ask HR directly: what will you say when someone calls? These companies have lawyers. You should have information. I wrote the Layoff Survival Guide with my husband Pav, who spent his career in HR leadership. He’s conducted layoffs, negotiated severance from the other side, and coached people through it. Grab the free guide: https://lnkd.in/gXgahYY9
104

Jenny Stojkovic

Entrepreneurship

2mo

I paid a tax strategist $13,000 to learn this. My son has been earning income since he was born. By the time he's 59½, his Roth IRA will be worth $5.7 million. Tax-free. Here's the strategy the wealthy have used for generations: Pay your child for legitimate work in your business. Write it off as a business expense. Invest it in a Custodial Roth IRA that grows tax-free for decades. This isn't new. The wealthy have done this forever. DJ Khaled listed his son Asahd as executive producer on his album at 7 months old. Drake used his son Adonis's artwork as his album cover. The Kardashian kids appear in content, campaigns, and brand shoots constantly. These aren't just cute moments. They're tax strategies. The math is simple: → $7,000/year contributed (the Roth IRA max) → Contributions from age 0 to 17 → 8% average annual return By age 18: $283,000 By age 59½: $5.7 million After age 18, no more contributions needed. It just compounds for 41 years. Three key benefits: 1. Tax deduction for you (business expense) 2. Tax-free growth for them (Roth IRA) 3. Financial literacy from birth Most people overlook this: A Roth IRA beats a 529 plan on flexibility. 529s are education-only and have rollover limitations. If your kid skips college (or AI makes it useless), you pay penalties and taxes. A Roth IRA is theirs forever. Contributions can be withdrawn anytime, tax-free. No restrictions. Total flexibility. I know from experience that getting the details right — like documentation, IRS compliance, choosing investments, and structuring payments correctly — can be tricky. So I put together a free guide with everything I learned. Grab it here: https://lnkd.in/gvVPKsgR Are you already doing this for your kids? 👋🏼 Follow Jenny Stojkovic for more content from a mom VC. ♻️ Share this with a parent who needs to see it.
965

Jenny Stojkovic

Entrepreneurship

2mo

Would you rather have 10,000 LinkedIn followers or 100,000 Instagram followers? 👀 That's the question Lana Ivory 🦋, expert in creator marketing in AI at Meta, and I discussed this week at the Meta campus in LA. It's here: the rise of knowledge creators. And we agreed on something that might ruffle some feathers. The quality of your audience matters more than the size. Would you rather have 10,000 LinkedIn followers or 100,000 Instagram followers? Not even up for a debate. Here's why LinkedIn hits different: → The decision makers are here. VPs. Directors. Execs. → The person reading your post could be a Fortune 500 buyer, not a teenager in their parents' basement → You're building your network BEFORE you need it That last point is crucial. If you start building your network after you need it, you're coming from a place of desperation. You're not being authentic. You're being reactive. And here's the thing no one talks about: AI is changing the future of work faster than most people realize. The people who are creating knowledge content TODAY are going to be miles ahead when they need to pivot, launch a business, or land their next opportunity. Your 9-to-5 can become your 5-to-9. And that employee-generated content you're posting under YOUR profile? That belongs to YOU. It can be the foundation of becoming a knowledge creator independently. So if you're waiting for "the right time" to start posting on LinkedIn... I don't know what you're waiting for. The riches are in the niches. Start sharing what you know. Ready to go all in on owning your OWN brand? Join our next The Women Creators event in April: https://lnkd.in/gcNMkzba P.S. Shoutout to John Kraski, the GOAT who intro'ed us!! ❤️
230

Jenny Stojkovic

Entrepreneurship

2mo

This 82 year old CEO is worth $7.8 billion and has never taken a single investor. And you've probably never heard her name. Meet Judy Faulkner, Founder and CEO of Epic Systems. Judy grew up in Cherry Hill, New Jersey. Her father was a pharmacist. Her mother directed Oregon Physicians for Social Responsibility. She earned a math degree from Dickinson College, then a master's in computer science from the University of Wisconsin-Madison where she took one of the first courses ever taught on computers in medicine. She wrote the original code herself. In 1979, Judy started Epic Systems from a basement with $70,000 and two part-time assistants. The goal: digitize medical records and put the patient at the center. When her partner pushed to raise venture capital, she said no. Losing control was non-negotiable. She never took a single outside investor. Never acquired another company. Never went public. Her 10 commandments start with: "Do not go public. Do not acquire or be acquired." By 1995, Epic had 100 clients and 125 employees. Today, Epic holds 325 million patient records. Clients include Mayo Clinic, Johns Hopkins Medicine, and Cleveland Clinic. The company generates $5.7 billion in annual revenue with 13,000 employees on a 1,670-acre campus in Wisconsin. Forbes named her "the most powerful woman in healthcare." Her net worth is $7.8 billion. She's pledged 99% of it to charity through the Giving Pledge. In 2019, she and her husband Gordon, a retired pediatrician who gave free care to children for 15 years, founded the Roots & Wings Foundation to support low-income kids and families. CNBC described her as "a female cross between Bill Gates and Willy Wonka." At 82, she still shows up to work every day. Her dog Tundra sits by her desk. She has no plans to retire. "It never occurred to me to do anything other than put the patient at the center." What makes Judy remarkable is that she actually wrote the code that powers Epic. She didn't just lead the company, but she built the product. Few CEOs can say that. Judy may be the most important woman in healthcare technology, yet this post might be the first time you've ever heard of her. That's why I share the stories of women execs and founders like Judy every Wednesday for #WomenFounderWednesday. Subscribe to Jenny Stojkovic for more.
1.1K

Jenny Stojkovic

Entrepreneurship

2mo

AI was supposed to replace creators. Instead, it made them more valuable. I just published a new article in Rolling Stone: "How the AI Boom Fueled the Creator Boom." The creator economy is now worth $254 billion globally and is projected to hit $480 billion by 2027. Here's the paradox nobody expected: AI made content creation absurdly easy. But distribution became the bottleneck. When every company can build similar features at similar speeds, the battleground shifts to who people trust. And that's where B2B creators are winning. The data tells the story: → 84% of creators now use AI tools—but winners aren't pumping out more content. They're using AI to go deeper, not wider. → ~60% of Google searches end without a click. Reddit, Inc. threads are training the LLMs. For B2B creators? That's white space. → LinkedIn Thought Leader Ads see 2x higher CTR than traditional ads. → Creator Match 🧩 paid out $1M+ to LinkedIn creators recently (AJ Eckstein 🧩) —80% of their lifetime revenue came in just the past few months. → Notion's "Notion Faces" campaign is being called the biggest LinkedIn creator campaign ever: 50+ creators, 60+ organic posts, cross-industry Slack sharing. → U.S. creator ad spend hit $37 billion in 2025, up 26% YoY (IAB). The millennial career transition is happening in real time. Knowledge workers are building personal brands, pivoting careers, and integrating AI tools. The bottom line: Being known for what you know might be the only durable competitive advantage left. Thank you to folks who helped on this article (Jeremy Boissinot, Gigi Robinson ®, Daniel McCallum, AJ Eckstein 🧩, Brandon Smithwrick 🧠). More to come soon! Full article in Rolling Stone: https://lnkd.in/g4_b8Yi3 Want to start your creator journey? Join our community and sign up for the next The Women Creators event: https://lnkd.in/g_memDPv 👋🏼 Follow Jenny Stojkovic for more on the creator economy and AI. ♻️ Share this with someone building their personal brand.
11 pages
81

Jenny Stojkovic

Entrepreneurship

2mo

AI was supposed to replace creators. Instead, it made them more valuable. I just published a new article in Rolling Stone: "How the AI Boom Fueled the Creator Boom." The creator economy is now worth $254 billion globally and is projected to hit $480 billion by 2027. Here's the paradox nobody expected: AI made content creation absurdly easy. But distribution became the bottleneck. When every company can build similar features at similar speeds, the battleground shifts to who people trust. And that's where B2B creators are winning. The data tells the story: → 84% of creators now use AI tools—but winners aren't pumping out more content. They're using AI to go deeper, not wider. → ~60% of Google searches end without a click. Reddit, Inc. threads are training the LLMs. For B2B creators? That's white space. → LinkedIn Thought Leader Ads see 2x higher CTR than traditional ads. → Creator Match 🧩 paid out $1M+ to LinkedIn creators recently (AJ Eckstein 🧩) —80% of their lifetime revenue came in just the past few months. → Notion's "Notion Faces" campaign is being called the biggest LinkedIn creator campaign ever: 50+ creators, 60+ organic posts, cross-industry Slack sharing. → U.S. creator ad spend hit $37 billion in 2025, up 26% YoY (IAB). The millennial career transition is happening in real time. Knowledge workers are building personal brands, pivoting careers, and integrating AI tools. The bottom line: Being known for what you know might be the only durable competitive advantage left. Thank you to folks who helped on this article (Jeremy Boissinot, Gigi Robinson ®, Daniel McCallum, AJ Eckstein 🧩, Brandon Smithwrick 🧠). More to come soon! Full article in Rolling Stone: https://lnkd.in/g4_b8Yi3 Want to start your creator journey? Join our community and sign up for the next The Women Creators event: https://lnkd.in/g_memDPv 👋🏼 Follow Jenny Stojkovic for more on the creator economy and AI. ♻️ Share this with someone building their personal brand.
11 pages
77

Jenny Stojkovic

Entrepreneurship

2mo

This 82 year old CEO is worth $7.8 billion and has never taken a single investor. And you've probably never heard her name. Meet Judy Faulkner, Founder and CEO of Epic Systems. Judy grew up in Cherry Hill, New Jersey. Her father was a pharmacist. Her mother directed Oregon Physicians for Social Responsibility. She earned a math degree from Dickinson College, then a master's in computer science from the University of Wisconsin-Madison where she took one of the first courses ever taught on computers in medicine. She wrote the original code herself. In 1979, Judy started Epic Systems from a basement with $70,000 and two part-time assistants. The goal: digitize medical records and put the patient at the center. When her partner pushed to raise venture capital, she said no. Losing control was non-negotiable. She never took a single outside investor. Never acquired another company. Never went public. Her 10 commandments start with: "Do not go public. Do not acquire or be acquired." By 1995, Epic had 100 clients and 125 employees. Today, Epic holds 325 million patient records. Clients include Mayo Clinic, Johns Hopkins Medicine, and Cleveland Clinic. The company generates $5.7 billion in annual revenue with 13,000 employees on a 1,670-acre campus in Wisconsin. Forbes named her "the most powerful woman in healthcare." Her net worth is $7.8 billion. She's pledged 99% of it to charity through the Giving Pledge. In 2019, she and her husband Gordon, a retired pediatrician who gave free care to children for 15 years, founded the Roots & Wings Foundation to support low-income kids and families. CNBC described her as "a female cross between Bill Gates and Willy Wonka." At 82, she still shows up to work every day. Her dog Tundra sits by her desk. She has no plans to retire. "It never occurred to me to do anything other than put the patient at the center." What makes Judy remarkable is that she actually wrote the code that powers Epic. She didn't just lead the company, but she built the product. Few CEOs can say that. Judy may be the most important woman in healthcare technology, yet this post might be the first time you've ever heard of her. That's why I share the stories of women execs and founders like Judy every Wednesday for #WomenFounderWednesday. Subscribe to Jenny Stojkovic for more.
992

Jenny Stojkovic

Entrepreneurship

2mo

"Will AI take my job?" It's the most common message in my inbox every day. And the data isn't reassuring. Meta is cutting 20% of its staff. Oracle will slash up to 45,000 positions. In 2025 alone, 55,000 jobs were explicitly attributed to AI. Goldman Sachs estimates up to 300 million jobs globally could be affected. And we're only getting started. So I brought my husband Pav in for a deep dive on what to do if this happens to you. For those who are new here: Pav spent his career in HR leadership, including as Chief People Officer at The Athletic (acquired by the New York Times). He's conducted layoffs, coached people through them, and negotiated severance from the other side of the table. Here's what most people don't know: 1. Severance is almost never take-it-or-leave-it. Employers have flexibility on pay, benefits, equity, and non-competes. The worst they can say is no. 2. If you're 40+, the law requires your employer to give you at least 21 days to review a severance agreement. Most people sign in 48 hours because they don't know this. 3. Forwarding work emails to your personal account? That's one of the biggest mistakes Pav sees. It can violate your agreement and cost you your severance. These are just a few of the many things you should know. These companies have lawyers. You should have information. Pav and I put together a complete guide covering everything from negotiating severance to protecting your money, health coverage, legal rights, and your story. Get the guide here: https://lnkd.in/gXgahYY9 Have you experienced a layoff? How did you get through it? ♻️ Reshare this post. 📩 Send this post to someone who needs to see it. 👋🏼 Follow Jenny Stojkovic for more.
4 pages
61

Jenny Stojkovic

Entrepreneurship

2mo

The layoff numbers are staggering. Meta laid off hundreds of employees yesterday. Block just cut nearly half its workforce — with Jack Dorsey saying AI made it possible to run the company with a “significantly smaller team.” Oracle may slash up to 30,000 positions to fund AI data centers. Intel, UPS, Accenture, Verizon — tens of thousands of jobs each. And most people walking into those conversations have no idea how much leverage they actually have. Here’s what I wish more people knew: → If you’re 40+, federal law requires at least 21 days to review a severance agreement. If they rushed you, that waiver may not be enforceable. → Severance is almost never take-it-or-leave-it. You can negotiate pay, benefits, equity, even removing your non-compete. → If 50+ employees were laid off without 60 days notice, look into the WARN Act. You may be owed back pay. → Get your reference language in writing. Ask HR directly: what will you say when someone calls? These companies have lawyers. You should have information. I wrote the Layoff Survival Guide with my husband Pav, who spent his career in HR leadership. He’s conducted layoffs, negotiated severance from the other side, and coached people through it. Grab the free guide: https://lnkd.in/gXgahYY9
96

Jenny Stojkovic

Entrepreneurship

2mo

Would you rather have 10,000 LinkedIn followers or 100,000 Instagram followers? 👀 That's the question Lana Ivory 🦋, expert in creator marketing in AI at Meta, and I discussed this week at the Meta campus in LA. It's here: the rise of knowledge creators. And we agreed on something that might ruffle some feathers. The quality of your audience matters more than the size. Would you rather have 10,000 LinkedIn followers or 100,000 Instagram followers? Not even up for a debate. Here's why LinkedIn hits different: → The decision makers are here. VPs. Directors. Execs. → The person reading your post could be a Fortune 500 buyer, not a teenager in their parents' basement → You're building your network BEFORE you need it That last point is crucial. If you start building your network after you need it, you're coming from a place of desperation. You're not being authentic. You're being reactive. And here's the thing no one talks about: AI is changing the future of work faster than most people realize. The people who are creating knowledge content TODAY are going to be miles ahead when they need to pivot, launch a business, or land their next opportunity. Your 9-to-5 can become your 5-to-9. And that employee-generated content you're posting under YOUR profile? That belongs to YOU. It can be the foundation of becoming a knowledge creator independently. So if you're waiting for "the right time" to start posting on LinkedIn... I don't know what you're waiting for. The riches are in the niches. Start sharing what you know. Ready to go all in on owning your OWN brand? Join our next The Women Creators event in April: https://lnkd.in/gcNMkzba P.S. Shoutout to John Kraski, the GOAT who intro'ed us!! ❤️
204

Jenny Stojkovic

Entrepreneurship

2mo

I paid a tax strategist $13,000 to learn this. My son has been earning income since he was born. By the time he's 59½, his Roth IRA will be worth $5.7 million. Tax-free. Here's the strategy the wealthy have used for generations: Pay your child for legitimate work in your business. Write it off as a business expense. Invest it in a Custodial Roth IRA that grows tax-free for decades. This isn't new. The wealthy have done this forever. DJ Khaled listed his son Asahd as executive producer on his album at 7 months old. Drake used his son Adonis's artwork as his album cover. The Kardashian kids appear in content, campaigns, and brand shoots constantly. These aren't just cute moments. They're tax strategies. The math is simple: → $7,000/year contributed (the Roth IRA max) → Contributions from age 0 to 17 → 8% average annual return By age 18: $283,000 By age 59½: $5.7 million After age 18, no more contributions needed. It just compounds for 41 years. Three key benefits: 1. Tax deduction for you (business expense) 2. Tax-free growth for them (Roth IRA) 3. Financial literacy from birth Most people overlook this: A Roth IRA beats a 529 plan on flexibility. 529s are education-only and have rollover limitations. If your kid skips college (or AI makes it useless), you pay penalties and taxes. A Roth IRA is theirs forever. Contributions can be withdrawn anytime, tax-free. No restrictions. Total flexibility. I know from experience that getting the details right — like documentation, IRS compliance, choosing investments, and structuring payments correctly — can be tricky. So I put together a free guide with everything I learned. Grab it here: https://lnkd.in/gvVPKsgR Are you already doing this for your kids? 👋🏼 Follow Jenny Stojkovic for more content from a mom VC. ♻️ Share this with a parent who needs to see it.
844

Jenny Stojkovic

Entrepreneurship

2mo

This 42 year old CEO was born to refugees who escaped Vietnam on a sinking boat. Then, she sold her company for $875 million. Meet Tracy Young, Founder and CEO of TigerEye. Tracy grew up in Milpitas, California. Her parents were Chinese-Vietnamese refugees who fled the Vietnam War in 1977. They were on a fishing boat for 8 days with 300 refugees. Starving. No coast guard wanted to pick them up. They bribed an oil rig to sink their boat so they'd be rescued. They made it to California through a priest and worked multiple jobs. Her dad drove a taxi. Her mom worked swing shifts building ships. Eventually, they built a wholesale food distribution business and put all three kids through college. Tracy became a construction engineer. One day, she had to check 800 rooms in a hospital. She lugged 50 pounds of paper blueprints around in a cart. She ordered 15 extra sets of blueprints for one meeting. The bill? $27,000. That night, she went for drinks with her college friend. He'd just bought the first iPad. He slammed the table and said: "This is ridiculous. All of this should be on this iPad." That was the start of PlanGrid. In 2011, Tracy and her co-founders started building the company. One of her co-founders, Antoine, was diagnosed with a rare form of cancer right before they applied to Y Combinator. He passed away in January 2012. Before he died, he told Tracy: "Life is short. Take care of the ones you love. Don't be afraid to try new things. Never do anything that makes you unhappy." They got into Y Combinator. She kept building. Tracy sold most of PlanGrid on her own -- up to $5 million in revenue. She personally called every lead. When they couldn't afford conference booths, they ran demos in the hallway. Two of their top 10 customers came from those early hustle days. By 2018, PlanGrid had 500 employees. Over 1 million construction projects in 195 countries. $100 million in annual recurring revenue. Autodesk acquired PlanGrid for $875 million. When investors used to direct questions to her male co-founders instead of her, she responded by sponsoring conferences for women in construction and mentoring female entrepreneurs. In 2022, she started her second company, TigerEye, with her husband. They raised $35 million. "I am truly starting this company as an activist. If the world needs another company led by a woman, here I am. My parents were refugees of war. They didn't get to choose what they worked on. But I get to." What makes Tracy remarkable is that she didn't just build a tech company. She built it in construction, one of the least tech-forward industries on earth, while being a woman in a field that is 97% male. Tracy may be one of the most successful female founders in tech history, yet this post might be the first time you've ever heard of her. That's why I share the stories of women execs and founders like Tracy every Wednesday for #WomenFounderWednesday. 🔔 Subscribe to Jenny Stojkovic for more.
940

Jenny Stojkovic

Entrepreneurship

2mo

I wasn’t qualified. But I showed up anyway. When I applied to speak at my first big conference, I had no formal training. It was the biggest tech conference in the world. And I had no public speaking experience. No TED Talk. No portfolio. What I did have was a story and something worth saying. So I sent the email. Hit submit. Took the mic. Was I nervous? Absolutely. Was I perfect? Not even close. I fumbled more than once. But people listened. They nodded. They clapped. And afterward, someone came up to me and said, “That was their favorite talk of the entire conference.” That’s when I realized: confidence doesn't come from credentials. It comes from courage. So the next time you feel unqualified, remember: most of us are making it up as we go. You just have to ask yourself: Why not me?
177

Jenny Stojkovic

Entrepreneurship

2mo

My last boss was worth $12 billion. Working for him shattered everything I thought I knew about how business actually works. Here are the three toughest lessons I learned: 1. Network = Net worth I once watched a $50M deal close over dinner. No pitch deck. No due diligence. Just two people who'd known each other for 15 years and a handshake. Almost every great deal is funded by relationships. This is why repeat founders get the same VCs back, time and time again. Nothing can replace in-person meetings. Find your way to San Francisco, New York, or wherever your industry's leaders are. No cold email or internet DM will ever come close. 2. Almost everything is Chatham House Rule I've been in rooms with world leaders, top tech CEOs, billionaires, and celebrities. The kind of gatherings people suspect exist but can't prove. These meetings all have the same rule: you can share what you learned, but never who told you. If you break this rule even once and get caught running your mouth — you're done. You'll never be invited back. Ever. 3. Investors hate remote work I'm not going to sugarcoat this: most VCs don't take remote-first startups seriously. I know the internet told you remote work is the future. But the investors writing the checks? They want to see your team grinding together in-person. Look at the AI race happening right now. Teams are flooding back to San Francisco. Rents are skyrocketing again. That's not a coincidence. The reality of how business operates is often very different from what you see on social media. Which of these have you learned the hard way? Follow Jenny Stojkovic for more stories of an unlikely VC. 🔔
163

Jenny Stojkovic

Entrepreneurship

2mo

This 29 year old went from being a ballerina in Brazil to becoming the world’s youngest self-made female billionaire. Meet Luana Lopes Lara, Co-founder of Kalshi. Luana grew up in Brazil and spent her teens training as a ballerina at the Instituto Escola Do Teatro Bolshoi No Brasil. From an early age, she learned discipline the hard way, dancing up to 10 hours a day and performing on stages across Europe. It wasn’t until a short stint as a professional ballerina in Austria that Luana realized she wanted a different future. She moved to the United States to study computer science and math at MIT, where she dove into coding, cognitive science, and quantitative finance. During school, she interned at major hedge funds, learning how markets move and how people make decisions under uncertainty. In 2018, Luana teamed up with fellow MIT grad Tarek Mansour to launch Kalshi, a fully regulated prediction market where anyone can trade on real world events, from inflation numbers to elections. At first, regulators and Wall Street doubted them. For 18 months, they fought to convince the US government to approve a brand new type of exchange, eventually winning a landmark license and opening the first regulated event contract marketplace in America. Fast forward to 2026: A fresh funding round of $1 billion dollars valued Kalshi at around $22 billion dollars. With her ownership stake, Luana’s net worth crossed $2.6 billion dollars, officially making her the world’s youngest self made woman billionaire. Yes, even beating Taylor Swift. So, how did she do it? 1. An obsession with discipline. → Years of elite ballet training built her resilience, focus, and work ethic. 2. Leaving comfort behind. → She walked away from a ballet career, moved countries, and bet everything on learning hard technical skills. 3. Building where others were afraid to try. → Instead of launching another consumer app, she spent years navigating regulation to build a legal market in one of the most controversial areas of finance. Creating a fully regulated prediction market worth billions in your twenties is no small feat. Luana is living proof that grit, discipline, and bold decisions can rewrite the trajectory of a life. Side note: I'm not a fan of prediction markets, but this story is pretty insane. 👋🏼 Follow Jenny Stojkovic for more stories of women in business. ♻️ Share this story with an entrepreneur or small business owner who needs to see it.
8 pages
228

Jenny Stojkovic

Entrepreneurship

2mo

My last boss was worth $12 billion. Here are 10 lessons he taught me on relationships: 1. No assholes. He rejected investing in Uber because Travis was a terrible person. He knew it would be a billion dollar company and passed anyway. 2. Write everything down. Every conversation, every commitment, every detail. He never forgot because he never relied on memory. 3. Never ask for a favor right away. He'd meet someone and build a relationship for years before ever asking for anything. Sometimes decades. 4. Learn the names of their people. He always knew the name of someone's partner or kids. It wasn't a trick — it was respect. 5. Take interest in their life. He'd ask about a sport, a hobby, a trip they mentioned once. People remembered that he remembered. 6. Repeat their name. When he met someone new, he'd say their name over and over in that first conversation. It stuck. 7. Celebrate wins. Acknowledge losses. He always sent congratulations for successes and condolences for hard times. LBJ had the same rule. 8. Answer emails immediately. Leaving people on read was rude. Period. 9. If it's a no, say it fast. He never danced around it. A quick no is more respectful than a slow maybe. 10. Respect everyone equally. Whether it was an executive assistant or Jeff Bezos, he treated them the same. (Fun fact: He used to tell me Bezos was "the cheapest SOB you'd ever meet." 😂) The reality of how business operates is often very different from what you see on social media. Which of these rules do you use? Follow Jenny Stojkovic for more stories of an unlikely VC. 🔔
230

Jenny Stojkovic

Entrepreneurship

2mo

My son turned six months old this week. Last week, he grabbed a stacking ring, held it, and spent four attempts figuring out how to get it on the post. No instructions. No answer key. Just trial, error, and adjustment until he got it. Then I opened my phone and saw a school promising to make teenagers millionaires using AI by graduation, or give you your tuition back. Entry-level job postings dropped 35% between 2023 and mid-2025. Goldman Sachs estimates 300 million jobs globally could be disrupted by generative AI. The old playbook, good grades, good college, good job, is breaking down in real time. So my husband Pav Stojkovic, a former Chief People Officer, and I started asking: what does a kid actually need to know by 2040? Not credentials. Not memorized answers. How to learn. How to think critically. How to build and ship real things. How to manage money. And how to be the kind of human no model can replicate. These aren’t soft skills. They’re survival skills.
214

Jenny Stojkovic

Entrepreneurship

2mo

My son turned six months old this week. Last week, he grabbed a stacking ring, held it, and spent four attempts figuring out how to get it on the post. No instructions. No answer key. Just trial, error, and adjustment until he got it. Then I opened my phone and saw a school promising to make teenagers millionaires using AI by graduation, or give you your tuition back. Entry-level job postings dropped 35% between 2023 and mid-2025. Goldman Sachs estimates 300 million jobs globally could be disrupted by generative AI. The old playbook, good grades, good college, good job, is breaking down in real time. So my husband Pav Stojkovic, a former Chief People Officer, and I started asking: what does a kid actually need to know by 2040? Not credentials. Not memorized answers. How to learn. How to think critically. How to build and ship real things. How to manage money. And how to be the kind of human no model can replicate. These aren’t soft skills. They’re survival skills.
246

Jenny Stojkovic

Entrepreneurship

2mo

My last boss was worth $12 billion. Here are 10 lessons he taught me on relationships: 1. No assholes. He rejected investing in Uber because Travis was a terrible person. He knew it would be a billion dollar company and passed anyway. 2. Write everything down. Every conversation, every commitment, every detail. He never forgot because he never relied on memory. 3. Never ask for a favor right away. He'd meet someone and build a relationship for years before ever asking for anything. Sometimes decades. 4. Learn the names of their people. He always knew the name of someone's partner or kids. It wasn't a trick — it was respect. 5. Take interest in their life. He'd ask about a sport, a hobby, a trip they mentioned once. People remembered that he remembered. 6. Repeat their name. When he met someone new, he'd say their name over and over in that first conversation. It stuck. 7. Celebrate wins. Acknowledge losses. He always sent congratulations for successes and condolences for hard times. LBJ had the same rule. 8. Answer emails immediately. Leaving people on read was rude. Period. 9. If it's a no, say it fast. He never danced around it. A quick no is more respectful than a slow maybe. 10. Respect everyone equally. Whether it was an executive assistant or Jeff Bezos, he treated them the same. (Fun fact: He used to tell me Bezos was "the cheapest SOB you'd ever meet." 😂) The reality of how business operates is often very different from what you see on social media. Which of these rules do you use? Follow Jenny Stojkovic for more stories of an unlikely VC. 🔔
355

Jenny Stojkovic

Entrepreneurship

2mo

This 29 year old went from being a ballerina in Brazil to becoming the world’s youngest self-made female billionaire. Meet Luana Lopes Lara, Co-founder of Kalshi. Luana grew up in Brazil and spent her teens training as a ballerina at the Instituto Escola Do Teatro Bolshoi No Brasil. From an early age, she learned discipline the hard way, dancing up to 10 hours a day and performing on stages across Europe. It wasn’t until a short stint as a professional ballerina in Austria that Luana realized she wanted a different future. She moved to the United States to study computer science and math at MIT, where she dove into coding, cognitive science, and quantitative finance. During school, she interned at major hedge funds, learning how markets move and how people make decisions under uncertainty. In 2018, Luana teamed up with fellow MIT grad Tarek Mansour to launch Kalshi, a fully regulated prediction market where anyone can trade on real world events, from inflation numbers to elections. At first, regulators and Wall Street doubted them. For 18 months, they fought to convince the US government to approve a brand new type of exchange, eventually winning a landmark license and opening the first regulated event contract marketplace in America. Fast forward to 2026: A fresh funding round of $1 billion dollars valued Kalshi at around $22 billion dollars. With her ownership stake, Luana’s net worth crossed $2.6 billion dollars, officially making her the world’s youngest self made woman billionaire. Yes, even beating Taylor Swift. So, how did she do it? 1. An obsession with discipline. → Years of elite ballet training built her resilience, focus, and work ethic. 2. Leaving comfort behind. → She walked away from a ballet career, moved countries, and bet everything on learning hard technical skills. 3. Building where others were afraid to try. → Instead of launching another consumer app, she spent years navigating regulation to build a legal market in one of the most controversial areas of finance. Creating a fully regulated prediction market worth billions in your twenties is no small feat. Luana is living proof that grit, discipline, and bold decisions can rewrite the trajectory of a life. Side note: I'm not a fan of prediction markets, but this story is pretty insane. 👋🏼 Follow Jenny Stojkovic for more stories of women in business. ♻️ Share this story with an entrepreneur or small business owner who needs to see it.
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254

Jenny Stojkovic

Entrepreneurship

2mo

My last boss was worth $12 billion. Working for him shattered everything I thought I knew about how business actually works. Here are the three toughest lessons I learned: 1. Network = Net worth I once watched a $50M deal close over dinner. No pitch deck. No due diligence. Just two people who'd known each other for 15 years and a handshake. Almost every great deal is funded by relationships. This is why repeat founders get the same VCs back, time and time again. Nothing can replace in-person meetings. Find your way to San Francisco, New York, or wherever your industry's leaders are. No cold email or internet DM will ever come close. 2. Almost everything is Chatham House Rule I've been in rooms with world leaders, top tech CEOs, billionaires, and celebrities. The kind of gatherings people suspect exist but can't prove. These meetings all have the same rule: you can share what you learned, but never who told you. If you break this rule even once and get caught running your mouth — you're done. You'll never be invited back. Ever. 3. Investors hate remote work I'm not going to sugarcoat this: most VCs don't take remote-first startups seriously. I know the internet told you remote work is the future. But the investors writing the checks? They want to see your team grinding together in-person. Look at the AI race happening right now. Teams are flooding back to San Francisco. Rents are skyrocketing again. That's not a coincidence. The reality of how business operates is often very different from what you see on social media. Which of these have you learned the hard way? Follow Jenny Stojkovic for more stories of an unlikely VC. 🔔
193

Jenny Stojkovic

Entrepreneurship

2mo

I wasn’t qualified. But I showed up anyway. When I applied to speak at my first big conference, I had no formal training. It was the biggest tech conference in the world. And I had no public speaking experience. No TED Talk. No portfolio. What I did have was a story and something worth saying. So I sent the email. Hit submit. Took the mic. Was I nervous? Absolutely. Was I perfect? Not even close. I fumbled more than once. But people listened. They nodded. They clapped. And afterward, someone came up to me and said, “That was their favorite talk of the entire conference.” That’s when I realized: confidence doesn't come from credentials. It comes from courage. So the next time you feel unqualified, remember: most of us are making it up as we go. You just have to ask yourself: Why not me?
241

Jenny Stojkovic

Entrepreneurship

2mo

OpenAI just merged the tech + creator economy. Here’s why. 👇🏼 So, OpenAI just bought a YouTube show. And everyone’s asking the wrong question. They’re debating whether AI companies should own media. But that’s not what’s happening here. AI is the media. TBPN is a daily 3-hour live stream that launched in 2025. $5M in ad revenue its first year. On track for $30M this year. Zuckerberg, Nadella, and Sam Altman have all sat down with them. No outside investors. Profitable from day one. Deal terms weren’t disclosed — but at that revenue trajectory, you’re looking at a $100M+ acquisition. A classic acqui-hire. But more importantly: OpenAI also just hired Charles Porch, the man who helped Beyoncé launch an album exclusively on the platform. He onboarded the Pope to Instagram. He built the creator economy as we know it. This means only one thing. OpenAI isn’t building an AI company that dabbles in media. They’re building the next social media platform — and they know that whoever controls the cultural conversation about AI is AI in the public’s mind. They just hired the people who made it.
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Jenny Stojkovic Recent LinkedIn Posts | EXEED AI