Executive coaching for employees is complicated and emotional

Welcome to Startups Weekly, a fresh human-first take on this week’s startup news and trends. To get this in your inbox, subscribe here. 

BetterUp, a reskilling and coaching platform for employees before and beyond the C-suite, is getting in touch with its emotions. This week, the richly funded unicorn startup announced a pair of acquisitions in the emotional artificial intelligence and people management space: Motive and Impraise. The terms of the deal weren’t disclosed. 

BetterUp announced its acquisitions after a busy stint, which included passing $100 million in annual recurring revenue, expanding to Europe, and hitting 1 million individual coaching sessions on its platform. 

I’ll be honest. It’s par for the course to see a growth-stage startup use milestones to inorganically expand through acquisitions. How else do you grow into your valuation? BetterUp’s duo of deals still stood out to me because they signal a somewhat unconventional direction for where the coaching industry is going. Stay with me.

BetterUp claims that it pioneered the category of coaching by focusing on employees, not just C-suite executives. With these acquisitions, it’s shifting how that coaching looks and lives. Motive, for example, will help BetterUp clients understand the emotional context behind data that they already aggregate, through engagement surveys or polls. It’s a plug-and-play approach that helps employers more immediately act on employee sentiment, instead of waiting for the long-game of coaching to play out. 

On the other end of the funnel, Impraise uses technology to help managers better support their direct reports, through real-time performance reviews and more seamless feedback channels. Like Motive, Impraise is a step outside of the traditional boundaries of what coaching looks like. 

“The direct-report relationship is where change happens in people’s lives,” BetterUp CEO and co-founder Alexi Robichaux said. “It doesn’t actually happen in coaching sessions; change happens after.”

In some ways, these acquisitions are BetterUp admitting that coaching for all employees has to be an end-to-end solution that requires everyone in the company – from HR to managers – to be involved. It can’t be a weekly calendar invite. This sort of investment could cause employers to shy away from even offering services to their staff to begin with, but pressure to retain may force them to try anyways. For other coaching and up-skilling platforms, the bar continues to be raised. 

“Coaching can be a point solution, but that’s not enough and we know that better than anyone because we invented the point solution,” Robichaux said. “If you don’t have the data platform, if you don’t have the outcomes. If you don’t have the AI to personalize this, you can go coach 50 managers at your company,” but not every employee.

In the rest of this newsletter, I’ll walk us through Atlanta’s big bootstrapped moment, Casper’s nightmare and Apple’s day. As always, you can find me on Twitter @nmasc_ and listen to my podcast, Equity.

Atlanta’s big bootstrapped moment

Step aside Austin and Miami, Atlanta is in town. All eyes were on the city this week after Intuit bought local business Mailchimp for a staggering $12 billion. The Atlanta-based email marketing company never took any outside funding, which meant the deal was one of the biggest ever for a bootstrapped company. And while some saw Mailchimp’s massive exit as a win for the Atlanta startup and venture ecosystem, others felt differently. 

Here’s what to know: Part of Mailchimp’s strategy as an untraditional tech company included not giving Mailchimp employees equity, and prioritizing profit-sharing as well as higher salaries. It sounds good, until your startup exits for $12 billion and you realize you don’t have any equity in the business that you helped build. It’s a knock against bootstrapping, as we discussed during Equity. Employees spoke to Business Insider about their first reactions, answering if the deal does indeed empower the local ecosystem.  

Outside the inbox:

Casper’s nightmare

Image Credits: Bryce Durbin/TechCrunch

My scoop this week uncovered that Casper, the direct-to-consumer mattress company, had another round of layoffs that impacted two dozen employees, as well as its CMO, CTO and COO. The round of layoffs and executive shuffle comes a little over a year since Casper cut 21% of its workforce and shut down its European operations.  

The easy take here is that Casper is struggling with management and direction and has been on its back foot since its public debut last year. However, I’d argue that there’s more nuance here.

Here’s what to know: One founder in the direct-to-consumer space, who spoke on the condition of anonymity due to her lack of direct knowledge with the company said that Casper’s layoffs could also be a response to Apple’s iOS 14.5 update, which will crack down on apps that track users’ data without permission. The setting restricts the advertising data that companies can access, making it harder to justify budget and understand the efficacy of their sales strategy.

For DTC companies, the uncertainty of in-person retail activity plus difficulty of advertising attribution is a challenging hurdle to surpass.

Don’t sleep on this:

Apple (a) day

Apple went back on stage with yet another virtual event to announce updates, upgrades and brand new unveils. The TechCrunch team, of course, couldn’t resist a chance to live blog. Read our full coverage here

Here’s what to know: It was all about the new iPhone 13. Brian Heater explained the context around the launch and what’s actually new about the smartphone. 

Last year’s iPhone 12 was a massive seller, bucking the trend of stagnating smartphone sales, in part due to a bottleneck in sales from the unplanned delay, but also because it finally brought 5G connectivity to Apple’s mobile line.

Lucky number iPhone 13 (no skipping for superstition’s sake, mind) features a familiar design. The front notch has finally been shrunken — now 20% smaller than its predecessor — while the rear-facing camera system has also gotten a redesign. The screen is now 28% brighter, Super Retina XDR display on both the iPhone 13 and 13 mini at 1200 nits.

On and off the stage:

Around TC

Our prep sessions are done. The Battlefield companies are amped. And a photo booth is coming.

TechCrunch Disrupt kicks off next week! Our flagship event, featuring speakers like Melanie Perkins and Reid Hoffman, runs virtually September 21 to 23. The events team has truly spent months on making this a virtual event that feels engaging, spontaneous and true to our personality as a publication. And after getting a sneak peek this past week, I can promise you that it’s different from any other online conference that I’ve attended during the pandemic.

Anyways, all this is to say that I’m amped to join the stage with my colleagues, interview the brightest names in tech, and meet as many entrepreneurs as possible. Are you joining? Buy tickets using my discount code “MASCARENHAS20.” 

Across the week

Seen on TechCrunch

Facebook knows Instagram harms teens. Now, its plan to open the app to kids looks worse than ever

Inside Reach Capital’s edtech-powered returns

Canva’s problem with PDF and its $40B valuation

Seen on Extra Crunch

3 strategies to make adopting new HR tech easier for hiring managers

What could stop the startup boom?

The value of software revenue may have finally stopped rising

Edtech leans into the creator economy with cohort-based classes

Reid Hoffman is returning to Disrupt

You’ve probably learned from Reid Hoffman before, either through his inventions, investments or inspirational words. The entrepreneur is the co-founder of LinkedIn, a partner at Greylock and the author of a new book based off of his hit podcast, Masters of Scale. 

His storied past makes him chock-full of interesting anecdotes and lessons, which is why we’re excited to have him back on the TechCrunch Disrupt stage happening next week from September 21-23. I’ll sit down with him to learn about his perspective on some of the biggest tensions that entrepreneurs face today. Hoffman’s advice is often fueled by his raw conversations with top tech CEOs and founders, so we’ll broaden access to his speed-dial list to understand how even his own perceptions on blitzscaling, growth and entrepreneurship are changing amid the pandemic. As I explained in my review of his new book, his words read like a well-networked mentor giving you a pep talk — so even if you’re not building a startup, there will be useful lessons to learn just by listening.

Here’s how it impacted my interview process, for example:

While press wasn’t a main character in the book, “Master of Scale” has already changed my perspective on how I interview founders. Lessons from Tristan Walker made me want to ask more questions about founders, and their most controversial beliefs, rather than how they plan to spend their new round of funding. A note from Andrés Ruzo made me realize that a startup that makes too much sense might be a comfortable read, but it might not be a moonshot that disrupts the world; in other words, pursue the startups that have too much seemingly foolish ambition — because they may be where the best strides, and stories, are made. Finally, it confirmed my belief that the best litmus test for a founder is if they are willing to talk about the hardships ahead of them in an honest, humble way.

OK, that’s all I’m hinting. Join me at Disrupt, where I’ll put Hoffman on the hot seat, balance out the cheerfulness with some cynical takes and push him to explain what his inevitable next book is about. Buy your tickets to TechCrunch Disrupt using this link, or use promo code “MASCARENHAS20” for a little discount from me.

Inside Reach Capital’s edtech-powered returns

Reach Capital, a San Francisco-based venture firm co-founded by Jennifer Carolan and Shauntel Garvey, focused exclusively on edtech for years before the sector ballooned with unicorns. The rare, female-led partnership closed its third fund in February, a $165 million vehicle and its largest to date. That said, returns from its previous funds show that the early bet on a now-revitalized sector is paying off.

Reach Capital’s second fund, an $82 million vehicle closed in 2017, posted a net internal return rate of 72.1% as of Q2 2021, according to data intended for LPs and obtained by TechCrunch. The fund, which put investments into Paper, Winnie and now-unicorns Handshake and Outschool, ranks multiple percentage points above the top quartile of funds of that vintage. According to Cambridge Associates data, the top quartile of funds of that vintage had a net IRR of 47.64% the same quarter.

By comparison, Reach Capital’s first fund was multiple percentage points below the top quartile of fund performers of its vintage year, 2015.

It’s worth noting that Reach Capital’s returns for its second fund are mostly paper gains, meaning that the net IRR is based on an uptick in valuations. Given the fact that the firm is heavily concentrated in follow-on rounds, the IRR is thus a snapshot of a single moment of its performance in time. Reach recently had its first cash exit, seeing portfolio company Ellevation merge with Curriculum Associates, but that is not represented in the data.

A number of blooming startups may explain what’s driving the improved performance between Reach I and Reach II. Per an impact report, Reach II invested $32 million into 14 core investments, including Newsela, Handshake and Outschool, all companies that have now gone to pass the billion-dollar valuation mark, making them unicorns. It also put money into Paper, which recently landed a nine-figure round led by IVP. By getting into those companies early, and then watching them get marked up as edtech booms as a category, Reach’s positions get validated.

The diversity of Reach II’s portfolio beats industry averages, but the founders are still concentrated as white and male. About 74% of investments are founded by men, while 26% are founded by women, the report states. About 62% of founders identify as white, 20% identify as Asian, 14% identify as LatinX and 4% identify as Middle Eastern. There are no Black founders in Reach Capital II’s portfolio.

Reach’s impressive returns come at a time when venture more broadly is booming. A number of investors and founders spoke on background to offer context about whether the returns are impressive for a seed-stage fund of that vintage. One investment strategist said that, while it’s not unheard of in this environment, the return percentage is “crazy good.”

“Easily upper quartile and probably upper decile,” they said. “Unless we are talking crypto, in which case it’s pretty ordinary.” A separate seed-stage investor pointed to Fred Wilson’s recent blogpost “Cash on Cash vs IRR,” alluding to the idea that holding periods can skew fund performance data.

Still, Reach’s returns offer an impressive window into how one of the most diverse partnerships in venture capital is performing within one of the most revitalized sectors in startupland. The momentum isn’t going unnoticed. Filings show that Reach is raising money for a $50 million opportunity fund. The company has been on a hiring spree as of late, too, bringing on Jomayra Herrera from Cowboy Ventures as a partner and Tony Wan from EdSurge as head of investor content.

Casper cuts its CMO, CTO and COO amid further layoffs

Casper has laid off dozens of employees, including three C-Level executives: its chief marketing officer, chief technology officer and chief operating officer, sources say. The mattress company declined to comment.

The round of layoffs, communicated to employees on Friday, largely impacted retail and operations teams, signaling that the business may be undergoing a broader restructuring. Laid-off employees were offered severance packages.

Notably, the impacted executives were all fairly recent additions to the team. CTO Ben Clark has been with the company since July 2019, while former CMO Lisa Pillette joined Casper in March 2020. Casper COO Charles Liu had only been at the company for eight months before this round of layoffs.

Casper’s CFO remains at the startup, but that role has had some significant turnover as well. In an April 2020 business update, Casper announced that Gregory Macfarlane, its CFO and COO at the time, was leaving the company. Interim CFO Stuart Brown eventually took the role, and three months later resigned. The latest CFO, Michael Monahan, took the position effective August 31, 2021.

Over a year ago, Casper announced it was shutting down its European operations, cutting 21% of its global workforce. The move was then attributed to Casper’s new goal of  “achieving profitability,” which included a focus on North American operations.

The business hinted then that the temporary closure of its retail stores impacted its overall direct-to-consumer channel, forcing it to take steps to minimize operating costs. Now, the startup is going one step further by eliminating roles within its retail and operations teams.

One founder in the direct-to-consumer space, who spoke on the condition of anonymity due to her lack of direct knowledge with the company, said that Casper’s layoffs could also be a response to iOS 14.5, Apple’s latest software that will crack down on apps that track users’ data without permission. The setting restricts the advertising data that companies can access, making it harder to justify budget and understand the efficacy of their sales strategy.

“Performance marketing through paid channels, specifically Facebook and Instagram, is wonky right now,” the person said. “So, if they were really reliant on that channel that could be something that is affecting their sales.”

Casper priced its IPO shares at $12 and debuted at $14.50 a share just as the COVID-19 pandemic was gaining momentum in February 2020. The company dove nearly 72% from its opening price before recovering, reaching a more recent peak of nearly $11 in February 2021. Today, the company trades at just above $5, a decline of more than half from its opening.

The next big startup may just help venture back more startups

Welcome to Startups Weekly, a fresh human-first take on this week’s startup news and trends. To get this in your inbox, subscribe here. 

Oper8r, built by Winter Mead and Welly Sculley, wants to help new entrants in the VC world scale. The accelerator launched last year as a “Y Combinator for emerging fund managers,” built to help solo capitalists and people launching rolling funds grow up.

The idea was that a well-networked, smart individual may be able to raise their first $10 million in a debut fund off of connections, but when it comes time to scale to a $50 million or $200 million fund, managers need to have a sophisticated understanding of how the LP world works.

Now, Mead claims that all 18 graduates within his first cohort, which include Stellation capital, Maple VC, Interlace Ventures and Supply Change Capital, have successfully closed funds. Its second cohort is still in the fundraising process, but across both cohorts, over $500 million has been closed. Oper8r is launching its third cohort next week and soon will announce the launch of Cr8r, an early-stage program to help talented angel investors grow their investment cadence.

Oper8r’s expansion comes as the rate of first-time venture fundraising grows as well. The Wall Street Journal’s Yuliya Chernova wrote a story this week about how, after years of being on the decline, the rate of first-time venture fundraising in the United States is “on track to reverse course.” The story, pulling analysis from advisory firm Different Funds, states that “in the second quarter of this year, some 40% of venture-fund announcements, which includes funds just setting out to raise capital, were made by debut funds, whereas they represented between roughly 20% and 30% of fund announcements in each quarter over the past two years.”

This data screams that the rise of a solo GP, or an ambitious rolling-fund-turned-venture firm, isn’t a one-off, it’s an actual trend. This means there’s more pressure for venture firms to go beyond a scout program when it comes to supporting the next big investors — and there’s more of a market for formal efforts to scale operations.

Mead, meanwhile, is cooking up ways to add validation and signal to Oper8r. Many accelerators write checks to further validate their choices, but also to tap into the access they’re getting by helping budding entrepreneurs before top-tier LPs and VCs notice them. He hinted that Oper8r may pursue a similar strategy as it seeks to be the go-to for emerging managers.

“I think capital speaks louder than educational programs,” he said. “If you’re putting money into the opportunities you’re engaged with, I think it serves as a greater signal than someone just coming through the program.”

In the rest of this newsletter, we’ll discuss the creator economy’s latest dance, international BNPL week, and why I’m putting Reid Hoffman in the hot seat. As always, you can find me on Twitter @nmasc_ and listen to my podcast, Equity.

Edtech wants to have its creator economy moment, and it’s complicated

Image Credits: Bryce Durbin / TechCrunch

Edtech and the creator economy certainly differ in the problems they try to solve: Finding a VR solution to make online STEM classes more realistic is a different nut to crack than streamlining all of a creator’s different monetization strategies into one platform. Still, the two sectors have found common ground in the past year — as encapsulated by the rise of cohort-based class platforms.

Here’s what to know: I wrote about how the overlap of both sectors is leading to some complications during the rise of cohort-based classes. Some fear that turning creators into educators could bring in a rush of unqualified teachers with no understanding of true pedagogy, while others think that the true democratization of education requires a disruption of who is considered a teacher.

Edtech extras: 

TTYL, BNPL

Image Credits: Bryce Durbin / TechCrunch

This week on Equity, Mary Ann and I made sense of what felt like international BNPL week: PayPal acquired Japan’s Paidy for $2.7 billion, Zip bought Africa’s Payflex and Addi raised $75 million to prove BNPL’s power in LatAm.

Here’s what to know: The global boom is partly in response to e-commerce trends, partly in response to consumer demand for more flexibility when it comes to financing. The market isn’t a winner-takes-all, so expect more well-capitalized startups buying their way into consumer markets outside of their geography.

Other news of note:

Reid Hoffman on the hot seat

Reid Hoffman

Image Credits: Kelly Sullivan/Getty Images for LinkedIn

I read Reid Hoffman’s podcast-turned-new-book “Masters of Scale” over the past few days. The entire time, I felt like a well-networked mentor was giving me a pep talk, with name-drops that turned into generalist advice and a behind-the-scenes look at humanity’s decisions.

Here’s what to know: While the book gave me a needed boost of optimism, I still had some critiques. I felt like the book’s choice to not talk much about the ugly within startupland creates an imbalance of sorts. It would have benefitted from talking directly about divisive dynamics, ranging from how WeWork’s Adam Neumann impacted the way we talk about visionary founders, Brian Armstrong’s Coinbase memo and what it means for startup culture, or even the role of the tech press today.

So, I have an idea. Let’s balance out the cheerfulness with the cynical, and let’s do it live. I’m interviewing Hoffman at TechCrunch Disrupt this year, where I’ll put him on the hot seat and push him to explain some of the choices he made in the book. Other people I’m excited to see at the show include Peloton’s CEO and chief content officer and Ryan Reynolds.

Buy your tickets to TechCrunch Disrupt using this link, or use promo code “MASCARENHAS20” for a little discount from me.

Around TC

I’ll be honest, all we’re talking about internally these days is one thing: Disrupt, Disrupt, Disrupt. Here’s the agenda for the Disrupt Stage, which includes three virtual days of nonstop chatter on disruptive innovation.

Across the week

Seen on TechCrunch

Seen on Extra Crunch

And that’s it! Didn’t feel like a short week at all, huh?

Talk soon,

N

Quizlet plans for IPO over a year after hitting unicorn status

Quizlet, a flashcard tool turned artificial intelligence-powered tutoring platform, is planning an initial public offering nearly a year after it was valued at $1 billion. According to people familiar with the matter, Quizlet is considerably far along in the process to go public. A recent job filing shows that it is hiring for senior roles to “help build the financial systems and processes as we move towards an IPO.”

In an email to TechCrunch, the San Francisco-based edtech startup declined to comment. Quizlet hasn’t said much about its revenue specifics or if it’s profitable. Last year, the still-private startup claimed it was growing revenue 100% annually. On its website, Quizlet says that it has 60 million monthly learners, up 10 million learners compared to its 2018 totals.

Quizlet has built a large-scale business around simple to share and simple to use products. Its free flashcard maker helps students spin up study guides on topics to prepare for exams. Those insights fuel Quizlet Plus, the startup’s subscription product that charges $47.88 a year for access to more features, including tutoring services.

Quizlet’s tutoring arm, also known as Quizlet Learn, is the company’s most popular offering, per CEO Matthew Glotzbach. As a student goes through the system, Quizlet Learn consistently assesses students to see where they are making mistakes — and where they are making progress.

“It obviously doesn’t yet replace and can’t come anywhere close to replacing a human, but it can provide that guidance and point you in the right direction and help you spend your time in the right places,” he said. “Just even helping you set goals is such a critical step in learning.”

Most recently, Quizlet announced the launch of explanations, a feature that offers a step-by-step solution guide for problem sets from popular textbooks. The feature is “written and verified by experts” and is aimed to help “students better understand the reasoning and thought process behind study questions so they can practice and apply their learnings on their own,” it said in a statement. It also reclaimed the Q from its less fortunate predecessor, amid an entire rebrand.

Quizlet’s quiet march toward the public markets has been slow yet steady. The startup was founded in 2005 by a 15-year-old, Andrew Sutherland. It was fully bootstrapped until 2015. Glotzbach, who was previously an executive at YouTube, then joined in 2016. The startup still doesn’t appear to have a CFO, which is rare for companies that are going public.

Quizlet has raised a majority of its $62 million in venture capital under Glotzbach. Now, investors in the company include General Atlantic, Owl Ventures, Union Square Ventures, Costanoa Ventures and Altos Ventures.

Quizlet’s pursuit of the public markets comes as other edtech companies are proving the market’s reception to the sector. Duolingo, for example, is another consumer-focused education company, albeit one that focuses on one vertical versus Quizlet’s choice to stay broad. Duolingo went public in July, and is currently trading above its open price at $169.75 per share.

 

BNPL is not a winner-takes-all game

Hello and welcome back to Equity, TechCrunch’s venture capital-focused podcast, where we unpack the numbers behind the headlines.

Natasha and Mary Ann took over this week’s show with Chris and Grace, which meant that our overdeveloped senses of curiosity filled up the script just fine (even on a somewhat short week). Unintentionally, today’s episode was built around a theme of inclusion — from auto-insurance to women’s health, and from payments to knowledge.

But here are some more specifics on what we got into:

Remember when we were all thinking about what “the new normal” would look like? Well, I guess it’s here.

Equity drops every Monday at 7:00 a.m. PDT, Wednesday, and Friday morning at 7:00 a.m. PDT, so subscribe to us on Apple PodcastsOvercastSpotify and all the casts.

Reid Hoffman’s latest book gives us 10 ways to rethink entrepreneurship

When you’re in the mood for a pep talk, who better to turn to than a well-networked, optimistic mentor who is naturally in your corner? That friendly shoulder is the role that “Masters of Scale” wants to play.

Inspired by LinkedIn co-founder and Greylock partner Reid Hoffman’s hit podcast, the new book, co-authored by Hoffman along with podcast executive producers June Cohen and Deron Triff, came out this week. Riddled with anecdotes and actionable takeaways, the book’s strength is wholly related to the sheer diversity of entrepreneurs that are represented in the text. Beyond sticking to tech leaders, the book draws lessons from Spanx founder Sara Blakely, Starbucks founder Howard Schultz and Union Square Hospitality Group CEO Daniel Meyer. Like any good mentor, the book is realistic. Mentors know you aren’t Bumble’s Whitney Wolfe Herd or Airbnb’s Brian Chesky yet, but can extract universally applicable lessons from those leaders so that you can relate to them.

While press wasn’t a main character in the book, “Master of Scale” has already changed my perspective on how I interview founders. Lessons from Tristan Walker made me want to ask more questions about founders, and their most controversial beliefs, rather than how they plan to spend their new round of funding. A note from Andrés Ruzo made me realize that a startup that makes too much sense might be a comfortable read, but it might not be a moonshot that disrupts the world; in other words, pursue the startups that have too much seemingly foolish ambition — because they may be where the best strides, and stories, are made. Finally, it confirmed my belief that the best litmus test for a founder is if they are willing to talk about the hardships ahead of them in an honest, humble way.

Through every feel-good story, I waited for the pandemic to be addressed. The pandemic’s impact on startup advice was largely isolated to a single chapter about the art of the pivot. Instead of interspersing advice on how to deal with the pandemic’s impact on venture capital, funding and markets more broadly, the book limited its references to the cataclysmic event. This choice keeps the advice smartly evergreen. That said, I felt like the book’s choice to not talk much about the ugly within startupland creates an imbalance of sorts. It would have benefitted from talking directly about divisive dynamics, ranging from how WeWork’s Adam Neumann impacted the way we talk about visionary founders, Brian Armstrong’s Coinbase memo and what it means for startup culture, or even the role of the tech press today. One could argue that the book never claims to be journalistic, and instead wanted to play the role of a cheerleading mentor, not a cynical one.

Writing a book based on a hit podcast isn’t necessarily a walk in the park. Audio is an entirely different medium from written text, and it takes a certain finesse to translate into text the charisma and humility of vocal banter. Hoffman and the authors thus certainly shine brighter in some stories than others, leaning heavily on a repeated, yet effective storytelling arc throughout the text: introduce problem, present aha moment, offer solutions and share universal lessons.

I read the book over a weekend; I recommend the same move for any aspiring entrepreneur, techie or startup journalist looking to pick up a copy. Reid and the coauthors will do a fantastic job connecting the dots of over 70 entrepreneurs for you, but the real magic will come from what happens when you pause in between the stories — either to Google a founder you resonate with, to change up your interview style or to finally start working on the idea you one day may just blitzscale.

Equity Monday: Women’s employment drops, as Delta’s drama continues

Hello and welcome back to Equity, TechCrunch’s venture capital-focused podcast where we unpack the numbers behind the headlines.

This is Equity Monday, our weekly kickoff to catch up on weekend news and prep for the days ahead. We’re here on Tuesday this week since us folks in the United States had off for labor day. You can follow the show on Twitter here, and while you’re at it, throw me a follow too.

  • Jobs report: Over the weekend, the US government posted the Jobs Report. It wasn’t ideal, with a sharp drop in percentage of women rejoining the workforce. I give you the startup angle, and talk about a somewhat poetic unicorn.
  • Instacart, meet Instagram: WSJ reports that new Instacart CEO Fidji Simo is expanding the grocery delivery store’s consumer-product advertising business, with a goal of hitting $1 billion in revenue next year. I riff on why this makes sense and what challenges the business make come up against.
  • Behemoths, beware: The largest Series A within Africa just closed, and it’s not even close. Wave is taking on telecom-led mobile money, now with four-big name backers. It’s not the only startup trying to take on a behemoth. I also gave a shout out to Glass, which wants to take on Instagram as a new go-to destination for photographers to share their content.

And that’s a wrap. I have a fun edtech piece coming out on Extra Crunch this week, so keep your eyes out for it.

Equity drops every Monday at 7:00 a.m. PST, Wednesday, and Friday at 6:00 a.m. PST, so subscribe to us on Apple PodcastsOvercastSpotify and all the casts!

What 377 Y Combinator pitches will teach you about startups

Along with a cadre of other TechCrunch folks, I spent this week extremely focused on one event: Y Combinator. The elite accelerator announced a staggering 377 startups as its Summer 2021 cohort. We covered every single on-the-record startup that presented and plucked out some favorites:

There’s something quite earnest and magical about spending literally hours hearing founder after founder pitch their ideas, with one minute, a single slide and a whole lot of optimism. It’s why I like covering demo days: I get tunnel vision into where innovation is going next, what behemoths are ripe for disruption and what founders think is a witty competitive edge versus a simple baseline.

That said, I will share one caveat. While YC is an ambitious snapshot, it’s not entirely illustrative of the next wave of decision-makers and leaders within startups — from a diversity perspective. The accelerator posted small gains in the number of women and LatinX founders in its batch, but dropped in the number of Black founders participating. The need for more diverse accelerators has never been more obvious, and as some in the tech community argue, is Y Combinator’s biggest blind spot.

This in mind, I want to leave you with a few takeaways I had after listening to hundreds of pitches. Here’s what 377 Y Combinator pitches taught me about startups:

  1. Instacart walked so YC startups could stroll. Instacart, last valued at $39 billion, is one of Y Combinator’s most successful graduates — which makes it even more spicier that a number of startups within this summer’s batch want to take on the behemoth. Instead of going after the obvious — speed — startups are looking to enhance the grocery delivery experience through premium produce, local recipes and even ugly vegetables. It suggests that there may be a new chapter in grocery delivery, one in which ease isn’t the only competitive advantage.
  2. Crypto’s pre-seed world is quieter than fintech. YC feels more like a fintech accelerator than ever before, but when it comes to crypto, there weren’t as many moonshots as I’d expect. We discussed this a bit in the Equity podcast, but if anyone has theories as to why, I’m game to hear ‘em.
  3. Edtech wants to disrupt artsy subjects. It’s common to see edtech founders flock to subjects like science and mathematics when it comes to disruption. Why? Well, from a pure pedagogical perspective, it’s easier to scale a service that answers questions that only have one right answer. While math may fit into a box that works for a tech-powered AI tutoring bot, arts, on the other hand, may require a little bit more human touch. This is why I was excited to see a number of edtech startups, from Spark Studio to Litnerd, focusing on humanities in their pitches. As shocking as it sounds, to rethink how a bookclub is read is definitely a refreshing milestone for edtech.
  4. Sometimes, the best pitch is no pitch at all. One pitch stood out simply because it addressed the elephant in the room: We’re all stressed. Jupe sells glamping-in-a-box and the profitable business likely benefited from COVID-19. I remember that because the founder used a portion of his pitch to tell investors to breathe, because it’s been a long two days. Being human, and more importantly, speaking like one, is what it takes to stand out these days.

On that note, exhale. Let’s move on to the rest of this newsletter, which includes nostalgic nods to Wall Street, public filings and my favorite new podcast. As always, you can find and support me on Twitter @nmasc_ or send me tips at [email protected].

A return to old school Wall Street

With so many new funds, solo-GPs and alternative capital sources on the market these days, founders are confused. Funding may have moved away from three dudes on Sand Hill Road, but it’s also become more fragmented, which means entrepreneurs need to be even more sophisticated in how they fill up their cap tables. This week, I interviewed one recently venture-backed startup that proposed a solution: a return to old school Wall Street. 

Here’s what to know: Hum Capital wants to help investors allocate their resources to ambitious businesses, perfectly. The startup seeks to emulate the world of old school Wall Street, which helped ambitious business owners find the best financing option for their goal, instead of today’s dance of startups trying to prove worthiness for one type of capital. In my story, I explained more about the business.

At this stage, Hum Capital’s product is easy to explain:

It uses artificial intelligence and data to connect businesses to the available funders on the platform. The startup connects with a capital-hungry startup, ingests financial data from over 100 SaaS systems, including QuickBooks, NetSuite and Google Analytics, and then translates them to the some 250 institutional investors on its platform.

From Hum to mmhmm:       

IPO filings & other hubbub

Image Credits: ansonmiao / Getty Images

When the pandemic began to impact startups, Toast was top of the list. The restaurant tech startup had a series of deep layoffs as many of its clients in the hospitality industry had to shut down. Months later, Toast reentered headlines with a dramatically different message: It’s going public, and here’s all of our financial data.

Here’s what you need to know: This week, Toast published its S-1, offering a portrait into how the startup was impacted by the COVID-19 pandemic and answering questions on why it’s going public now. After ripping apart the Warby Parker S-1, Alex had five takeaways from the Toast S-1. My favorite excerpt? Toast was smart to diversify beyond its hardware, hand-held payment processors:

Toast’s two largest revenue sources — software and fintech incomes — have posted constant growth on a quarter-over-quarter basis. Hardware revenues have proved slightly less consistent, although they are also moving in a positive direction this year and set what appears to be an all-time record result in Q2 2021.

Toast would have had a much worse second quarter last year if it didn’t have software revenues. And since then, its growth would not have been as impressive without payments revenues (its fintech line item, speaking loosely). The broad revenue mix that Toast built has proved to limit downside while opening lots of room for growth.

Butter or jam:

Around TC

You already bought your tickets to Disrupt right? If not, here’s the link, with a fancy discount from yours truly.

Now that that’s out of the way, I want you to listen to Found, TechCrunch’s newest podcast that focuses on talking to early-stage founders about building and launching their companies. Recent episodes include:

Across the week

Seen on TechCrunch

Seen on Extra Crunch

Talk next week,

N