Mike Maples Jr. is a prolific angel investor and co-founder of early-stage venture firm Floodgate. Over the years, he’s taken a lot of bets. Some have paid off handsomely (Twitter, Twitch, Lyft and Bazaarvoice, for example). Others have not. On today's episode of Equity, Mary Ann sat down with Mike to dig into a number of topics, including some of his most memorable investments, the one that got away, what he looks for when evaluating startups that pitch him - and what Godzilla has to do with it. We also talked a bit about his new book that he co-authored with Peter Ziebelman called “Pattern Breakers. Why some startups change the future.” Press play and join the conversation!

On today's episode of Equity, Becca's taking a look at news you might've missed over the holiday weekend here in the U.S., starting with the recent OpenAI security breach. While it doesn't seem that people have to be too worried about what the hackers actually accessed, the fact that it happened is worth paying attention to. TechCrunch's Devin Coldeway argues that AI companies are treasure troves of data and will likely become more of a target for hackers. Companies that work with the large AI companies should pay attention.  We also had an update on Fisker’s slide into bankruptcy. The EV startup, that you've already heard about on Equity, had a new update this week. The company asked its bankruptcy judge for permission to sell its remaining inventory for $14,000 a vehicle, a noticeable drop from the $70,000 Fisker was initially asking for. This has some fearing that this chapter 11 bankruptcy could turn into a chapter 7.  To close out, we looked at a new trend of venture funds helping seed investors exercise their pro rata rights and avoid their equity stake being diluted. This is interesting because while it could be good for smaller funds to have a way to maintain their equity stakes, pro rata rights discussions can get contentious and bringing more capital to the table won't necessarily help that.  Equity will be back on Wednesday with an interesting conversation between Mary Ann and  angel investor and Floodgate Co-Founder, Mike Maples Jr, so we’ll talk to you then!

What’s the common thread between Tesla, building startups, General Motors, venture capital and Lyft? Jon McNeill, co-founder and partner of DVx Ventures, joins TechCrunch editor Kirsten Korosec on Equity to discuss how Elon Musk’s pay package has influenced founders, when it makes sense to go light on cash and heavy on equity, and his firm’s unique approach to investing that eschews the traditional management fee structure. McNeill describes DVx as VC 2.0. The firm comes up with business ideas and builds them into a startup within the firm before it goes out to find the leadership team. To date, the firm has started and invested in 14 portfolio companies that span EVs and AI, SaaS, consumer tech and climate tech. McNeill also walks Equity through the startup creation process, managing risk and how to spot opportunities that can disrupt the market.

Mary Ann, Haje and Kirsten are back on the mic for this week's episode, which was is jam-packed with deals, hot topics, and the latest dramaaaaaa in the tech world. For Deals of the Week, Haje wanted to chat about Formation Bio, an AI-focused drug development startup that just raised a whopping $372 million in Series D funding, led by Andreessen Horowitz. Next, Kirsten broke down the surprising partnership between Volkswagen Group and Rivian and how its initial $1 billion investment could grow up to $5 billion. To wrap up our deals, Mary-Ann highlighted Nubank’s acquisition of Hyperplane, an AI-for-banks startup. Moving onto our themes, Haje took us on a deep dive into the fediverse, a decentralized network of social media platforms like Mastodon, Threads, and even Trump’s Truth Social. The fediverse has seen a surge in popularity, especially after Elon Musk acquired Twitter (now X). Mastodon, for example, has just about tripled its user base since Musk took over. The appeal lies in its decentralized nature, offering users more control and niche communities. Whether you’re a photographer, a journalism enthusiast, or just someone fed up with traditional social media, the fediverse has something for you. Last but not least, we discussed the ongoing debate around DEI (Diversity, Equity, Inclusion) in tech in a more controversial segment. Scale AI’s founder Alexandr Wang recently sparked a debate by advocating for MEI (Merit, Excellence, Intelligence) over DEI. This has drawn support from big names like Elon Musk and Palmer Luckey but also significant criticism. The stats are troubling: new women recruit levels in the U.S. data industry have dropped dramatically, and DEI-related job listings are down. Equity will be back on Wednesday with a new interview episode, so stay tuned!

Today, we’re bringing you a conversation from TechCrunch's StrictlyVC event in DC earlier this month, where TechCrunch Editor in Chief & General Manager Connie Loizos sat down with Luther Lowe, who serves as Y Combinator’s Head of Public Policy. Lowe joined the accelerator last fall from Yelp, where he was SVP of Public Policy. Connie and Luther touched on antitrust efforts to reign in big tech, Y Combinator’s impact, leadership and access to talent, and what competition, policy and regulation look like in the AI era. It’s a super interesting conversation so press play and listen in!

Equity is back with your Monday Morning news rundown! This morning, a press release from the European Commission named Apple as the first of tech’s so-called “gatekeepers” to be charged for violating the EU’s Digital Markets Act. Apple is one of six tech giants named by the European Commission as “gatekeepers” last year, alongside Alphabet, Amazon, ByteDance, Meta and Microsoft. While we continue to keep our eyes on the EU’s attempts to ensure a competitive marketplace, that’s not all we got into on the Equity podcast this morning. Rebecca Bellan led the show this morning and reported that X still has a Verified bot problem, but this time they came for TechCrunch writers (herself included). The experience had us wondering if X’s competitors will step up, and create platforms with more safety…and fewer bots. Rebecca also had an IPO update for our listeners this morning as Shein finally filed for its public debut in London, and we closed out our startup coverage with a look at Sir Jack A Lot’s startup for retail traders. The startup, which recently raised a $4.5 million seed round, had us hyped on the retail trading space and its continued growth. Finally, Haje closed out today’s show with a teardown for Feel Therapeutics. The startup recently raised a $3.5M seed deck to revolutionize mental health care with a science-forward approach that integrates wearable devices, mobile apps, and clinician dashboards. Hit play to hear how they did it!

This week, co-hosts Mary-Ann Azavedo and Haje Kamps were joined by the ever-insightful Kirsten Korosec to dive into the latest and greatest happenings in the startup world. Kicking things off, our trio of hosts break down three major deals of the week. First, there's Waabi, an autonomous trucking startup that just closed a whopping $200 million Series B round. Kirsten Korosec provides an inside look into how Waabi's AI-first approach is setting it apart in the crowded autonomous vehicle space and why investors are still willing to back big bets in this field despite the market's ups and downs. Next, they explore the intriguing case of Gynger, a fintech company that has raised $20 million led by PayPal Ventures. Mary-Ann explains how Gynger is shaking up the way startups handle tech purchases with its buy-now-pay-later model, working both with buyers and sellers to offer flexible payment terms. Kirsten and your trusty correspondent weigh in on the potential risks and rewards of this unique business model, especially in today's volatile economic environment. The third deal takes us into the realm of artificial intelligence with Safe Superintelligence. I'm delving into the story of OpenAI co-founder Ilya Sutskever’s new venture, which aims to develop general AI with a focus on safety. We discuss the ambitious goals of this startup and the challenges of balancing rapid advancement with the ethical considerations of creating superintelligent AI. After dissecting these deals, the conversation shifts to a sobering topic: the wave of bankruptcies that have hit the startup world in 2024. Kirsten provides a detailed analysis of the factors leading to these failures, with a spotlight on high-profile cases like EV startup Fisker and fintech service Synapse. The team discusses the common pitfalls that led to these companies' downfalls and what other startups can learn from their mistakes. But it's not all doom and gloom—our hosts wrap up with an exciting discussion about the future. They dive into Voodoo's acquisition of social media startup BeReal for $537 million. Mary-Ann explores the reasons behind this bold move, how Voodoo plans to integrate ads into BeReal's platform, and what this could mean for the landscape of social media. Kirsten and myself debate the potential success of this strategy and the broader implications for user engagement and authenticity in the age of digital advertising.

Last week, Brex announced that it would be ditching its co-CEO model, and today, Equity hosts Haje Kamps and Mary Ann Azevedo are taking a closer look at co-CEO teams and the effectiveness of the structure overall. Brex, founded in 2017 by Pedro Franceschi and Henrique Dubugras, initially thrived under the co-CEO structure, with Pedro focusing on internal operations and Enrique handling external relations. However, as the company grew, this setup began to slow decision-making, prompting a shift to a single CEO model. Pedro will now lead as the sole CEO, while Enrique transitions to Chairman of the Board. We discuss the broader implications and challenges of co-CEO leadership, highlighting how this change aims to enhance agility and appeal to investors as Brex eyes a potential public offering. We also explore other companies that have adopted or abandoned similar leadership models, providing a comprehensive analysis of the pros and cons of shared CEO responsibilities in the competitive tech landscape.

This week on Equity, we discussed some big news that really matters: How Black founders are addressing the diversity gap in AI chatbots. We’ve all noticed how OpenAI’s ChatGPT and other AI chatbot tools struggle with cultural nuance, often coming up with answers that reflect a largely Euro-centric worldview. Now, a handful of Black-owned chatbots and ChatGPT versions – like Latimer.AI, ChatBlackGPT and Spark Plug – have cropped up to ensure Black POVs are included in the AI conversation, and that Black founders get a cut of this trillion-dollar industry. That’s not all Rebecca talked about on Monday’s show. We also looked at how different social media companies are playing around with what’s real and what isn’t, an increasingly salient topic in the age of AI. On the one hand, we’ve got TikTok’s introduction of generative AI avatars, which creators and brands can use to speed up ad campaigns and spread them out to a global audience. And on the other hand, YouTube is experimenting with a “Notes” feature that lets users add context to videos. It’s an attempt to combat misinformation as AI threatens to inundate us all with deepfake and misleading political content in the lead up to the 2024 presidential election. In IPO Land, Rebecca touched on Tempus’s 9% rise and $441 million raise on its Nasdaq debut last Friday. The genomic testing and data analysis company, started by Groupon’s founder, need have only hinted at its future genAI integrations for investors to throw money at it. Meanwhile, Chinese e-commerce giant Shein is struggling to get Beijing to approve its London IPO, reports the Financial Times. Shein’s executive chair reportedly angered Chinese regulators last month by saying its corporate values meant it “could be considered a US company,” so now the retailer is trying to walk back on those comments. Shein is trying to raise £50 billion (US$64 billion) from its London IPO, and it needs Beijing on its side to do so.   Haje closed out today’s show with a teardown of Kinnect’s $250K angel deck. Founded just last year, the digital archive startup is already making waves with $100,000 in funding from Techstar’s Rising Stars program. Hit play to hear how they did it!

Welcome back to Friday Equity! In today’s episode Equity podcast, Mary Ann, Haje and Becca dug into three very different but all super interesting deals of the week. Haje wanted to discuss Raspberry Pi’s debut on the public market, and we all agreed that what this profitable company has managed to build – a tiny affordable computer that fits into the palm of your hand – is very neat. Mary Ann then wanted to talk about InScope, a fintech which just raised a $4.3 million seed round of funding led by Lightspeed Venture Partners to automate financial reporting. Becca got to riff on Meowtel, a niche – and also profitable – startup focused on cat-sitting that has raised just $1 million in venture capital over its nine-year life. The trio then talked about all the Apple news (largely AI-focused) that came out of WWDC and its potential impact on the startup world. They then turned their attention to Elon Musk’s reaction to Apple’s announcement that it would be integrating ChatGPT into its iOS. While he clearly wasn’t happy about it, we discussed what his true motives for threatening to pull Apple devices from his companies might be. That’s it for this week, but we’ll be back bright and early Monday with more tech and startup news. Talk soon!

Vanessa Larco, partner at New Enterprise Associates (NEA), believes that Generative AI’s impact on the world of SaaS could be huge. The investor joined Mary Ann Azevedo on Equity to talk through, among other topics, her theories about how GenAI could alter the pricing models SaaS businesses use when charging customers. Larco also touched on how incumbents’ AI strategies may impact the startup world in general and in particular, what Apple’s new intelligence offering might mean for founders, and why despite being a big believer in the enterprise, she’s also still bullish on consumer investing and what she looks for when evaluating startups in the space. It was a fun conversation, so press play and listen in!

Apple’s WWDC is just hours away, and we’re gearing up for big announcements on – you guessed it – AI. We're kicking off today’s episode of Equity with a list of what we can (and can't) expect from the highly anticipated developer conference. But that's not all we talked about this morning. Becca Szkutak also took a look at Byju’s alarming valuation drop. The news may not come as a surprise given the rocky year Byju’s has had, but as Manish Sing put it, its journey stands to be one of the most “spectacular startup slides in recent memory.” To close out, we had news of a new fund looking to give the Italian startup ecosystem a boost. We’re optimist about the Italian Founders Fund and what it could contribute to the market, so press play and join the conversation!

Mary Ann and Rebecca discussed Robinhood’s plans to buy European crypto exchange Bitstamp for $200 million in cash and why they weren’t really surprised by the news. The duo then dug into not just one but two exciting health-care related deals. Rebecca wanted to riff on Sword Health’s innovative AI-powered virtual physical therapy tech and recent fundraise and corresponding cool valuation bump. Mary Ann then brought up Eko Health, which just raised $41 million after getting FDA clearance to help detect the first signs of heart failure during a routine medical exam (really, how cool is that?!). From there, they got to grill transportation reporter extraordinaire Sean O’Kane about his in-depth investigation into the mess at electric vehicle manufacturer Fisker. Think hoods flying off and pinching parts from the production line kind of mess. Oof. From there, they talked about the drama at AI mortgage startup LoanSnap and how that company is being sued left and right among other things. On a more positive note, they then riffed about two very interesting fintech startups focused on Gen Z, Frich (which stands for ‘effin rich) and Fizz – the latter of which is a YC alum just raised $14.4 million in a seed round led by Kleiner Perkins.

Consumer startups have taken a hit when it comes to venture funding. But according to Eurie Kim, partner at Forerunner Ventures and founding member of All Raise, consumer is where it’s at. The investor joined Mary Ann Azevedo on Equity to talk through the intricacies of the space. She pointed out that last year, just 7% of seed capital went to consumer startups. Yet, research shows that consumer company performance has outpaced enterprise, Kim contends. Forerunner itself has backed the likes of Oura, Chime and Prose, among others.

Welcome to this week's Episode of Equity Monday. We're kicking off the week with a deep dive from this weekend into the demise of electric vehicle startup Fisker at the hands of its founders' whims. Fisker, which was founded by famed vehicle designer Henrik Fisker, is on the brink of bankruptcy after only having delivered a few thousand electric Ocean SUVs. Then, Rebecca Bellan talked about X's new rules to allow adult content (as long as it's "consensually produced," whatever that means), and why that's problematic for the safety of other users -- namely women, who are most often the targets of sexually explicit trolling and harassment. We also touched on Trump's TikTok debut, which came in the wake of the former president's felony conviction. To wrap up, Bellan also discussed a story that TechCrunch published over the weekend looking into the new trend of smaller, lesser-known investors getting shares of hot private AI companies like Anthropic, X.ai and Perplexity by using special purpose vehicles, or SPVs. The result has been a Wild West, high risk, buyer-beware situation, with SPV terms varying wildly. Haje closed out the show with another Pitch Deck Teardown, this time looking into the Angel pitch deck for RAW Dating App. RAW just raised a $3 million friends and family round to shake up the dating scene by shedding fake, TikTok-ified, heavily filtered photos and replacing them with a more genuine, unvarnished experience.

Welcome back to Equity Friday! In this week’s episode, Mary Ann, Becca Szkutak,and Haje Kamps tackled three deals of the week: xAI, Elon Musk has once again proven that his name alone can shake up the investment world, raising a staggering $6 billion for his AI startup. Solutions by Text, The Dallas-based company, which has been bootstrapped for over a decade, secured $110 million in funding. And WeatherXM, which is a company bringing Web3 into the weather forecasting space that raised $7.7 million in a Series A. Then they discussed the Synapse Collapse and what it means for the larger FinTech ecosystem. Synapse, a banking-as-a-service (BaaS) provider, filed for Chapter 11 bankruptcy leaving many startups and customers in the lurch. Lastly, the crew wraps it up by discussing Becca’s piece on who is (and is not) going to IPO this year and what that signals to the industry. That’s it for this week, but we’ll be back bright and early Monday morning with more tech and startup news, along with another round of Pitch Deck Teardown. Talk soon!

It’s no secret that the bar for startups to land a Series A has risen, but has it risen too high? According to Jenny Fielding, a co-founder and Managing Partner at Everywhere Ventures, startups are facing what she calls “The Series A Chasm.” In a post on X this month, Fielding said, “there’s a huge backlog of seed stage companies with nice traction – just not $3m ARR + 30% MOM growth kinda traction.” The post sparked a conversation online, and Fielding joined Haje Kamps on Equity to talk through it all. Looking beyond Fielding’s portfolio, we can see that the early stage storm has been brewing for quite some time. According to data from Crunchbase, seed companies have raised about $7 billion so far this year, which is down $1 billion year over year and down significantly in the later stages. Crunchbase has even taken to calling this a moment of “extended adolescence” for startups, with an increase in companies raising $5 million+ seed rounds instead of a Series A. Of course, this meant we had to address the AI elephant in the room, and the $135 million seed round Musk’s xAI raised last December. Note that after 6 months, the company behind Grok has already announced a $6 billion Series B round. It was an interesting chat, so press play and join the conversation!

We’re kicking off the short week with news about Elon Musk, and no, it’s not about X or Tesla. Instead, we’re talking about Musk’s other other company, xAI. In a blog post this weekend, xAI announced it raised $6 billion in Series B funding, confirming earlier reports that the AI startup was looking to raise at a pre-money valuation of $18 billion. The ongoing AI race was only the beginning of what we covered on today’s episode of Equity. This morning, Becca Szkutak dove deep into the collapse of Synapse, a banking-as-a-service company whose bankruptcy could impact an estimated 10 million end customers and 100 fintechs, including teen banking-focused Copper. To wrap up this morning’s news segment, we also discussed a report from The Washington Post that election officials and researchers are considering a new approach to combating misinformation called “pre-bunking.” Companies like Google are testing it out in the lead up to the European Union election, but we remain skeptical about how successful the technique could be. Haje closed out the show with another Pitch Deck Teardown, this time examining Berlin-based Terra One’s deck. The startup just raised a cool $7.5 million to make sure Germany’s clean energy isn’t going to waste. Listen through to the end to hear how they made it happen!

Say hi to the new Equity crew! To kick off today's show, Mary Ann invited her new co-hosts - Becca Szkutak, Rebecca Bellan, and Haje Kamps - to introduce themselves and shared a bit more about what they do here at TC. The team then jumped right into the news, starting with Techstars CEO Maëlle Gavet's announcement that she is leaving the company. For deals of the week, Rebecca wanted to talk about Farcaster, a blockchain-based social protocol that ​​invites developers to build other apps on top of it. The startup raised a $150 million round, news that had the Equity team asking, “Is crypto back?” Mary Ann dug into immigrant banking platform Majority securing $20M in funding after notching an impressive $40 million in ARR as of April. To close out, we riffed on the news that a bunch of tech majors made commitments to the safe development of their AI models, including a potential “kill switch.” While we felt the news was mostly positive, we are also skeptical, too. The team also discussed the challenging environment for emerging fund managers, and our surprise at just how many of them there are.

Today, we’re listening back to not one but two interviews from the other side of the globe, thanks to our new co-host Rebecca Bellan, who spent three years in Auckland, New Zealand. Late last year, Rebecca hopped across the Tasman to Australia to report on the startup scene in Australia, and came back to us with a temperature check on VC in the Antipodes. Rebecca spoke to two Aussie VCs: Dan Krasnostein from Square Peg and Gabrielle Munzer from Main Sequence. Rebecca and our guests dug into why early stage funding is popping off in the region, the government's role in growing a startup ecosystem, fintech, climate tech, and what it’s like to compete and collaborate with Silicon Valley.

The AI news continues this week, and we're kicking things off with OpenAI's deal with Reddit. Per the terms of the deal, OpenAI will get to use content from Reddit like posts and replies to train its AI, and Reddit will get access to some unspecified AI tools. Reddit's stock soared 11% in extended trading following the news. That's not all we talked about on today's episode of Equity. This morning, Rebecca Bellan also walked us through a new social media platform called Maven that wants to do away with likes, followers and clout-chasing in favor of more serendipitous internet exploration. Maven was co-founded by OpenAI alum Kenneth Stanley and is backed by Twitter co-founder Ev Williams. Speaking of Twitter, X.com is officially live as a platform. Annoyingly for Elon Musk, so is Twitter.com. Bellan also covered some fresh cybersecurity consolidation. Israeli security firm CyberArk has purchased Venafi out from Thoma Bravo for $1.54 billion -- that's $1 billion in cash and the rest in shares. Before you go, don't miss the latest Pitch Deck Teardown from Haje Kamps. In today's segment Haje digs deep on Berlin-based startup Goodcarbon's deck. The startup just raised a €5.25 million (around $5.5 million) seed round to make its mark on the big business of carbon credits, and its pitch deck does a great job at showing traction, but is not so great its team slide. Listen to the end to learn more!

This week, Mary Ann, Becca and Haje dug into three funding deals, proving that bigger is not always better (or more interesting). Becca wanted to talk about Spoor, an Oslo, Norway-based startup using AI to help wind farms mitigate its impact on birds (how cool is that?) while Haje wanted to discuss how fintech Layer is looking to take on QuickBooks in the SMB accounting space. Mary Ann, meanwhile, was excited to look into one Kentucky-based startup’s decision to raise $27.5 million in venture capital after being bootstrapped for six years and achieving profitability. We then moved on to AI-land, and all the fascinating new features revealed by OpenAI and Google this past week. And of course, we had to riff on what all of that means for startups. Last but not least, the trio examined the trend of venture capital investors leaving their firms to do other things – including starting their own new firms, or going back to old ones, in some cases. We're still wondering what could be behind all the moves, but it doesn't look like the trend is not going anywhere anytime soon. That’s it for this week but never fear, we’ll be back bright and early Monday morning with your tech and startup news, along with another round of Pitch Deck Teardown. Talk soon!

For months, TechCrunch Senior Reporters Mary Ann Azevedo and Christine Hall have been following the story of Newchip's bankruptcy and its impact on founders and today on Equity, they're joined by Haje Kamps to dig deep into how the accelerator’s fall from grace threatened the cap tables of thousands of startups.

Last week was a busy one for some Apple Store employees. Over the weekend, workers at Apple’s Townson, Maryland store — the first Apple retail store to have a formally recognized union — voted to authorize a strike. While the date of the strike is still being determined, the union has been negotiating with Apple since January 2023 over work-life balance, unpredictable scheduling, and wages, among other issues. But that wasn't all we discussed on today’s episode of Equity. This morning, Rebecca Szkutak also broke down what we can and can’t expect from OpenAI’s livestream event later today. On Friday, Sam Altman put a stop to rumors that the company will release a Google search competitor, but he did say OpenAI could announce a search feature within ChatGPT. To close out, Haje took the reins with another Pitch Deck Teardown. This time, we’re highlighting Cloudsmith, which secured $15 million for its cloud platform. The startup's 2021 round was the largest Series A for a company from Northern Ireland since 2005, so clearly they got a thing or two right. Listen through to the end to find out how the company pulled it off!

Finally, some good news! This week, we were pleasantly surprised to see that FTX victims would be getting some money back – even if it’s not as much as they might have hoped. That wasn’t all, though: Mary Ann Azevedo, Kirsten Korosec, and Alex Wilhelm had plenty else to talk about this week on Equity. We discussed why investors are drawn to the fact that Amae Health is building an in-person approach to mental healthcare in an increasingly digital space and also how one North Carolina startup that started out by building drones to clean windows in tall buildings has also become a robotics company. Kirsten helped us understand what was behind Motional’s decision to delay its commercial robotaxi plans amid restructuring, and the greater context around that. We then dug into digital banking startup Mercury’s plans to branch out into software, and how it now fits into the increasingly crowded spend management landscape. And, we riffed on the fact that we covered three M&A deals this week (read about them here, here and here) and how refreshing that was considering M&A activity has been lighter than expected. (Spoiler alert: AI was involved in at least two of them).