Alex Konrad
@alexrkonrad • 89,912 subscribers
Founder and editor of @upstartsmediaco, a new tech publication focused on the startup ecosystem. Previously @Forbes senior editor. Email: [email protected]
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"Survive. Don't sell. Don't quit." WRITER CEO May Habib (May Habib) has lived this mantra through a pivot, casual VC bias, and living in the shadow of the buzzier, brasher AI labs. "Anthropic and OpenAI salespeople walk in like heroes, get a contract, and leave to literally never be seen again,” she says. She's built Writer into a $1.9B valued business with customers like Accenture, Cigna and Vanguard anyway, by focusing on old-fashioned ROI, and AI tools built for "normal" people: non-coders who she argues are otherwise in danger of getting left behind. On this can't-miss episode of The Upstarts Podcast, Habib isn't pulling any punches 🥊 We talk tokenomics "insanity," and why she believes more accountability is needed In AI spending: "People should be getting f***ing fired." We also cover her pivot from Qordoba to Writer, and why Writer trains its own models, but doesn't want to be a lab. And she calls out as venture capital's ongoing gender bias -- including one famous firm that wrote that her mom status was "inspiring" while they passed 👀 This season is presented by Rippling 🫡 TIME STAMPS: 00:00 Introduction 1:55 How Writer helps ‘normal’ people 9:31 The temperature in the C-suite around AI 16:56 The killer use case for Writer’s tools 21:16 Pivoting from Qordoba to Writer 22:31 Vinod Khosla, Sequoia, and bias in VC 27:43 ‘Survive, don’t sell, don’t quit’ 30:33 Why Writer trains models, but isn’t a lab 33:38 Anthropic, OpenAI and how Writer can compete 40:52 Why people should be fired for buying AI badly Enjoy!
Alex Konrad133,678 views • 3 months ago
Salespeople have a problem: they only spend 21% of their time actually selling to customers 🤝 Mutiny CEO Jaleh Rezaei (Jaleh Rezaei) thought she'd found a way to fix it. She worked with customers like Snowflake and Uber. Revenue reached 8-figures 📈 Which makes what happened next all the more shocking: she burned it all down 🔥 On The Upstarts Podcast, Jaleh shares why she took the tough decision to fire her customers, slash headcount and re-found her startup around an AI agent. We go into AI's disruption of SaaS; her favorite advice from Fin's Des Traynor on pivoting and from Y Combinator's Garry Tan on showing the chart you don't want people to see; how to get over "Claude Spookies," and why speed is (mostly) all you need. This season of the show is presented by Rippling 🫡 CHAPTERS 00:00 Introduction 2:41 An AI agent for sales 7:04 Why an AI ‘blank canvas’ doesn’t work 10:38 Jaleh’s founder journey and Gusto lessons 17:01 Mutiny’s early software success 22:51 Jaleh’s Upstart Moment: tearing it down 24:42 Why you can’t rebuild a business halfway 27:15 Intercom’s founders share valuable advice 30:44 Focus on the business, not the optics 34:53 ‘Speed is the only thing that matters’ 37:40 ‘Claude spookies’ in the AI app layer 43:59 Second-time founder advantage Thanks for watching!
Alex Konrad99,147 views • 3 months ago
!["Vinod also fell asleep in my partner meeting at Khosla [Ventures]" 👀 The interactions with Vinod Khosla were "great" up until that point, though, remembers Writer CEO May Habib. Still, Habib (May Habib) says that in hindsight, it might have been easier for WRITER to raise its Series A if she'd had her male co-founder, CTO Waseem AlShikh (Waseem Shah), lead the pitches. "If you're a woman pitching VCs, we're all fooling ourselves to think that in the back of their minds, they think you'll work as hard," Habib says. "Have the technical man pitch." If that sounds cynical, Habib says she only cares about the outcome for her startup. Would Waseem have welcomed that? "I guess we'll find out when he hears this," she says. Catch the full episode on The Upstarts Podcast, presented by Rippling.](https://image.24vids.com/tw-2072047201816089048/amplify_video_thumb/2072047102570422272/img/8uYxcCwGiQhPh8wO.jpg)
"Vinod also fell asleep in my partner meeting at Khosla [Ventures]" 👀 The interactions with Vinod Khosla were "great" up until that point, though, remembers Writer CEO May Habib. Still, Habib (May Habib) says that in hindsight, it might have been easier for WRITER to raise its Series A if she'd had her male co-founder, CTO Waseem AlShikh (Waseem Shah), lead the pitches. "If you're a woman pitching VCs, we're all fooling ourselves to think that in the back of their minds, they think you'll work as hard," Habib says. "Have the technical man pitch." If that sounds cynical, Habib says she only cares about the outcome for her startup. Would Waseem have welcomed that? "I guess we'll find out when he hears this," she says. Catch the full episode on The Upstarts Podcast, presented by Rippling.
Alex Konrad72,886 views • 3 months ago
Nobody wants to be an accountant anymore. Basis CEO Matt Harpe thinks he can help. Founded in 2023 by Harpe and Mitchell Troyanovsky, Basis builds AI agents for accounting firms, automating hours of number crunching and copy-paste into a review process that takes minutes. Basis already works with 25% of the top 150 firms in the U.S. and reached a valuation of $1.15B in February. And far from eliminating jobs, Harpe believes his startup will help human accountants get paid. "It will increase how valuable accountants are, because they will be able to accomplish so much more," he says. On The Upstarts Podcast, Harpe shares: ▪️how Basis can stay ahead of the big labs like Anthropic and OpenAI in its vertical ▪️why outcome-based pricing is nice work, if you can get it ▪️how he pitches top AI talent in New York on building accounting tools, of all things. Plus, he shares his Upstart Moment: resisting calls to chase short-term revenue until his product felt ready for primetime. TIMESTAMPS 00:00 Introduction 01:47 The basis for Basis 07:25 Why no one wants to be an accountant any more 14:37 CEO Matt Harpe's founder journey 19:46 "The home for applied AI talent in New York" 22:58 Winning over skeptical accountants as customers 28:41 A big bet on agents from the start 31:31 Outcome-based pricing and its challenges 35:52 Competing with the big AI labs like OpenAI 41:11 Making human accountants more valuable A big thanks to our season sponsor, Rippling, for supporting founder stories like this 🫡 Enjoy!
Alex Konrad46,732 views • 2 months ago
"In the Series A, the Sequoia rejection included a line about how inspiring it was that I had two little kids at home while I was pitching them." -- WRITER CEO May Habib (May Habib) with some real talk on being a working mom in Silicon Valley 👀 "Everybody wants to hear you say that there is nothing more important to you than being a billionaire," she says. "And the reality is, my kids are more important than that." Now, when investors ask Habib about her family, her instinct is to stress that her in-laws take care of the kids, while she works 90 hours a week. "It's sad that's the instinct. At the same time, I know that if I weren't working that hard, if our whole team weren't working that hard, it would have been much harder to get to where we are today." Catch the full interview on The Upstarts Podcast, presented by Rippling 👇
Alex Konrad64,476 views • 3 months ago
Last week, Flexport released an AI agent that can audit bills from shippers and truckers against the actual logs to ensure its customers are invoiced correctly. The product was just an idea 3 days before. "We probably pivoted 30% to 40% of our engineers now just to building agents," founder Ryan Petersen (Ryan Petersen) says. "There's way less planning than there used to be at Flexport in the roadmap. It used to be a one year strategic plan. Now you're like, ‘Alright, let's go see if you can make this work, come back to me two days later.' And it works, because of AI.” Catch the full interview on The Upstarts Podcast: YouTube: Apple: Spotify:
Alex Konrad122,071 views • 7 months ago
"This is not a product category." "They're not actually going to work on this." "They're going to acquihire themselves to somebody." When Christina Cacioppo (Christina Cacioppo) first pitched her startup in 2018, investors couldn't believe anyone would want to build compliance software. Eight years later, Vanta works with 16K+ customers from Lovable to Icelandair, earning a $4.2B valuation. Now, she faces the opposite question: With AI, can't anyone build this? How does Vanta stay ahead of a new wave of hype-y startups? "I subscribe to the 'never let them see you blink' school of thought, she tells me. On The Upstarts Podcast, Cacioppo shares how she created value in a sleepy category; how she prioritizes “infinity things” as a startup unicorn CEO; and why when it comes to good security hygiene, we could all spend more time brushing our teeth. Plus, she shares her Upstart Moment: working to re-think, and future-proof, Vanta's software business in the face of powerful AI models. This season is presented by Rippling 🫡 CHAPTERS 00:00 Introduction 1:39 What Vanta does 5:26 Selling to other startups 9:28 How AI agents change ‘pretty much everything’ 14:06 Christina’s *real* founder origin story 16:23 Underdog fundraising and gaming VCs 18:59 The problem with startup valuations 24:08 Turning LinkedIn ‘cringe’ into customer traction 26:41 Reinventing Vanta with AI 33:43 Whether AI could clone Vanta 35:23 ‘Never let them see you blink’ 37:24 Avoiding burnout with ‘infinity things’
Alex Konrad57,500 views • 4 months ago
Flexport CEO Ryan Petersen still thinks about a 2012 essay written by Paul Graham called 'Schlep Blindness.' Every startup founder of a certain era of went through the misery of applying to accept credit card payments. But only Patrick and John Collison (Patrick Collison and John Collison) started Stripe. "There was a $100 billion opportunity available to every entrepreneur," says Petersen. "The worst problems in your life, your conscious brain is unable to focus, to think about them at all. You're just completely blind that this problem exists." More recently, Petersen (Ryan Petersen) says that PG (Paul Graham) has described his company, Flexport, the same way. "Anyone who ever imported anything wen through this pain, saw it's a nightmare to fill out paperwork, and no one call tell you where your stuff is, or when it's going to arrive." Catch the full discussion on The Upstarts Podcast 👇 YouTube: Spotify: Apple:
Alex Konrad69,560 views • 6 months ago
What happened when startup Axiom took the Putnam Competition, the world's hardest college-level math test? "We got the exam, and we are like, 'We are screwed,' CEO Carina Hong (Carina Hong) remembers of that December day. Famed mathematician Ken Ono (Ken Ono), who now works at Axiom, rallied the troops: There's no room for purity! We are in a sports situation! "It's really funny for a pure number theorist to say that," says Hong. At 3:58pm, two minutes before the deadline, Axiom solved its 8th problem. Hong really wanted 9. She debated whether to announce the news. "So the next morning, I just did the right thing, I announced it on Twitter. Two hours later, we got the ninth." Catch the full interview on The Upstarts Podcast.
Alex Konrad42,894 views • 5 months ago
Harvey CEO Winston Weinberg's big regret: not building in public. "There was a lot of secrecy in the beginning. If I would do things over again, I would have figured out how to build in public faster." Being secretive wasn't deliberate or a marketing ploy, but a function of being heads down trying to keep up with customers, Winston Weinberg says now. But it's contributed to some people accusing $11B-valued Harvey of selling "snake oil" to this day. "I think that a lot of folks in Silicon Valley, they don't know that many lawyers," he adds. "They think that oh, if you can just automate code development, you can for sure automate law immediately after." Catch the full episode on The Upstarts Podcast.
Alex Konrad44,134 views • 6 months ago
Ryan Petersen (Ryan Petersen) has turned posting like he's tech's 'hurricane reporter' around all things shipping and trade into a big platform, with 310K followers on X. His lesson for startups: nobody cares. "In general, nobody cares about your startup," Flexport's CEO tells The Upstarts Podcast. "They care about things that are happening that are relevant in their world, and they're only gonna care about you to the extent that you are." Audiences are also wise to self-promotion, he adds. "You have to figure out, okay, what, what's the thing that we can provide unique insight into?" Catch the full episode 👇 YouTube: Spotify: Apple:
Alex Konrad40,072 views • 6 months ago
News: Canada-based AI company Cohere is combining with German AI co Aleph Alpha at a reported $20B valuation. Last week on The Upstarts Podcast, Cohere CEO Aidan Gomez (Aidan Gomez) said Cohere wants to take a "friends with everyone" approach that means he turned down early investment offers from hyperscalers like Amazon, Google or Microsoft. "Even before all this geopolitical stuff, one of the core value props of Cohere was independence," he says. "If you're a large enterprise, you don't want to be completely locked into your cloud provider, one ecosystem, because they're just going to keep squeezing you."
Alex Konrad32,795 views • 5 months ago
News: Upstarts is launching our flagship podcast 🚀 Behind every world-changing business, there's an Upstart -- a founder who took on the status quo to achieve big impact 🌐 On The Upstarts Podcast, I'll chat with an up-and-coming startup leader each week about their 'Upstart Moment' and how they beat the odds 💪 You'll gain insight into transformative new technology, as well as real strategies and tactical tips for any busy builder to apply to their own work 🛠️ Early guests include: ▪️Canva CEO Melanie Perkins ▪️Valar Atomics CEO Isaiah Taylor - making nuclear reactors ▪️Loyal CEO Celine Halioua ▪️Star Catcher CEO Andrew Rush More founders in AI, aerospace, biotech, fintech and fertility to follow! Highlights and behind-the-scenes extras will be on Upstarts Media, too :)
Alex Konrad33,267 views • 7 months ago
"When you start a company, the expectation is failure." You can't build a great product. You can't hire great people. You'll never get good investors. You can't raise a Series A. You can't raise a Series B. Mutiny CEO Jaleh Rezaei (Jaleh Rezaei) had heard all of those doubts. She'd done all of it. And she started over anyway. "It's really hard to accept that you're going to burn that to the ground for the possibility of a better future," she says. After a year of working to add new AI capabilities to Mutiny's software, Jaleh felt she was "mashing" two different products together. On a walk along the Hudson River in November, she told co-founder Nikhil Matthew they had to make a radical change. Catch the full story on The Upstarts Podcast, presented by Rippling 🫡
Alex Konrad16,106 views • 3 months ago
Doctors are burned out. Patients don’t understand the advice they’re given. And the U.S. healthcare system is drowning each year in $1.5 trillion – with a “T” – in administrative costs. Abridge CEO Shiv Rao (Shiv Rao, MD) thinks he can help. A practicing cardiologist who still sees patients, he co-founded Abridge in Pittsburgh in 2018 to build the “AI operating system” for healthcare. Abridge's software automates the clerical work of a visit, from notes to billing, and increasingly assists with making clinical recommendations, too. "We think healthcare is the biggest opportunity for AI," Rao says. "We want to be deflationary, we want to save time, save money, and save lives." Valued at $5.3B, Abridge serves more than 300 health systems that reach 250M Americans, and recently partnered with Eli Lilly and Company and NVIDIA. But it faces plenty of potential competition, from giants like Microsoft, Epic Systems, and Palantir, to VC-backed rival Ambience, and maybe even the AI labs. On The Upstarts Podcast, Rao talks about how an early bet on AI got Abridge going, before ChatGPT; why reaching scale in healthcare requires years of “eating glass” and “kissing frogs;” and why he thinks Abridge can help doctors and nurses feel like “superheroes.” Plus, he shares his Upstart Moment: A “YOLO” decision to take on Microsoft head-to-head. This season is presented by Rippling. CHAPTERS 00:00 Introduction 02:16 What Abridge does for doctors, patients and hospitals 06:39 Solving the ‘conversation’ problem 10:45 From doctor to startup founder 18:48 “Eating glass” and “kissing frogs” early on 20:14 What IBM Watson got wrong 23:25 Why healthcare is a hard sell for startups 31:39 A “YOLO move” to go after Microsoft 37:42 Dealing with increasing competition 40:29 Working with NVIDIA, Anthropic and OpenAI 43:26 Shiv’s personal healthcare journey
Alex Konrad11,784 views • 2 months ago
"I don't think you need to worry about internal morale based off of external things that you see on Twitter." -- Harvey CEO Winston Weinberg (Winston Weinberg) His advice for founders: Structure your startup so that every employee has a good pulse for customer satisfaction. It'll be a better barometer than whether you're getting love on social media. That's the case at Harvey, where Weinberg says employees can find it jarring that despite lots of hype and a $11B valuation, he still sends memos telling everyone to move faster. "As long as your customers are happy, that's all that matters." Catch the full interview on our latest episode of The Upstarts Podcast from Upstarts Media 👀
Alex Konrad19,832 views • 6 months ago
"Speed should get you to somewhere that has more long-term advantages." - Decagon CEO Jesse Zhang (Jesse Zhang) At $4.5B-valued Decagon, speed is an advantage, not a moat. "If everyone is at the same starting line in the early days, it's just, how fast can you go?" Zhang tells Upstarts Media. "We really pride ourselves on our go-to-market execution, but that's not a long-term differentiator." So why does Decagon win accounts like big banks, airlines and telcos over competitors? While rivals are "hedging across a bunch of different approaches," Decagon takes an opinionated approach to encouraging customers to iterate within the product, Zhang argues. "They're like, 'Okay, yeah, we believe in this,'" he says. Catch the full interview on The Upstarts Podcast (links below) 👀
Alex Konrad18,276 views • 5 months ago
Can living brain cells unlock the next big breakthrough in AI? Neurosurgeon turned founder Alex Ksendzovsky thinks so. His startup The Biological Computing Co. (TBC) trains AI models that he claims are as much as 27x more efficient by taking advantage of the cheapest, best image processor available: the neuron. “I have about 500 million years of evidence behind me,” he says. “So our moat is evolution.” TBC has raised more than $25M and is already in the market with its models. But its CEO is chasing a future straight out of sci-fi: real-time biological computing happening inside data centers. “We’re bringing something completely crazy to the world, and we’re showing that it works." On The Upstarts Podcast, we discuss why algorithms derived by brain cells beat ones only inspired by the brain; why models were the best place to start; and the ethics of using living neurons for training AI. Plus, Ksendzovksy shares his Upstart Moment: giving up a promising career in academia to pursue a high-risk startup. CHAPTERS 00:00 Introduction 01:12 Building software from wetware 05:09 A college idea to predict the stock market 08:40 The first test from an Airbnb 12:46 Rat neurons and electrodes 17:30 Pitching VCs with no data 24:52 Promising early AI results 31:09 The ethics of using neurons 34:40 ‘Our moat is evolution’ 35:38 A real-time biological computing future This season of the show is presented by Rippling 🫡
Alex Konrad12,577 views • 3 months ago
Talked about the endorphin rush of breaking scoops with my guys John Coogan and Jordi Hays at TBPN. It can feel good to flex the muscles with a juicy one occasionally, but it's not my focus at Upstarts. I gladly leave the heavy lifting to 'scoop athletes' like Katie Roof 💪
Alex Konrad18,546 views • 6 months ago
"I was like, 'Yeah, of course, dude!' But it's very non-obvious if you haven't had that problem before." Loyal founder Celine Halioua shares on The Upstarts Podcast how one VC's mind was blown when they asked dog owner friends what they'd pay for her longevity drug 👀 Catch the full episode on YouTube: Apple: Spotify:
Alex Konrad16,445 views • 7 months ago