precursor ventures

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Precursor Ventures promotes Sydney Thomas, its first hire, to principal

In 2019, only one Black woman was named partner in venture capital, according to All Raise, a nonprofit focused on accelerating female founders and investors. The data has shown, shows, and will continue to show how the tech industry fails to invest in underrepresented women of color.

Thus, hiring the next generation of founders and decision-makers is key (and promoting them is, too).

Sydney Thomas, who was the first hire at Precursor Ventures, a seed and early-stage focused fund led by Charles Hudson, has been promoted from senior associate to principal. Thomas is joined by Hudson, analyst Ayanna Kerrison and entrepreneur-in-residence Chapman Snowden, to make up Precursor.

After graduating from the Haas School of Business at Berkeley in 2016, Thomas joined Precursor to do what Hudson says most applicants wouldn’t: the operational work of bringing a solo-GP fund, then with less than $5 million in committed capital, to a more organized place.

“The fund was basically running out of my inbox,” Hudson said. “She really helped us get to a much better place operationally.” Thomas started off as an intern, toggling time between working for a Precursor portfolio company and the fund itself, and eventually came on as a senior associate.

As a principal, Thomas will now have more discretion to do deals and make decisions for the firm. “The goal was always for her to get us to a place operationally where she wasn’t as critical,” Hudson notes. Thomas did not respond to request for comment.

Roles within venture have grown increasingly, and often intentionally, vague over time. At any given fund, there can be principals, investors, partners, investing principal partners and senior associate investors. Depending on the fund, each person could just go under the guise of “partner” and call it a day. But in action, every member on a venture team has a varying range of investment autonomy, decision-making authority and weight at the firm.

While the vagueness can balance out egos within a firm, it can often leave founders confused over who has the ability to give them money.

Hudson says he takes role differentiation seriously, and (patiently) wants to build Precursor into a place that helps people in venture get their first start. With Thomas’s promotion, she has the ability to green light investments without the mass overhead of what it means to be a partner.

“I think the only reason to make someone a principal is if you think that they could develop into a partner,” he said.

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With thousands of subscribers, The Juggernaut raises $2 million for a South Asian-focused news outlet

As paid newsletters grow in popularity, Snigdha Sur, the founder of South Asian-focused media company The Juggernaut, has no qualms about avoiding the approach entirely. In October 2017, Sur started The Juggernaut as a free newsletter, called InkMango. As she searched for news on the South Asian diaspora, she found that articles lacked original reporting, aggregation was becoming repetitive and mainstream news organizations weren’t answering big questions.

Then InkMango crossed 700 free readers, and Sur saw an opportunity for a full-bodied media company, not just a newsletter.

One year and a Y Combinator graduation later, The Juggernaut has worked with more than 100 contributors (both journalists and illustrators) to provide analysis on South Asian news. Recent headlines on The Juggernaut include: The Evolution of Padma Lakshmi; How Ancestry Test Results Became Browner; and How the Death of a Bollywood Actor Became a Political Proxy War. The network approach, instead of a single newesletter approach,aggreff is working so far: Sur says that The Juggernaut has garnered “thousands of subscribers.” During COVID-19, The Juggernaut’s net subscribers have grown 20% to 30% month over month, she said.

On the heels of this growth, The Juggernaut announced today that it has raised a $2 million seed round led by Precursor Ventures to hire editors and a full-time growth engineer, and expand new editorial projects. Other investors in the round include Unpopular Ventures, Backstage Capital, New Media Ventures and Old Town Media. Angels include former Andreessen Horowitz general partner Balaji Srinivasan; co-founder of Kabam, Holly Liu; and co-founder of sports-focused publication The Athletic, Adam Hansmann.

Currently, The Juggernaut charges $3.99 a month for an annual subscription, $9.99 a month for a monthly subscription and $249.99 for a lifetime subscription to the news outlet. It also offers a seven-day free trial (with a conversation rate to paid at over 80%) and has a free newsletter, which Sur says will remain free to bring in top-of-the-funnel customers.

The Juggernaut is part of a growing number of media companies trying to directly monetize off of subscriptions instead of advertisements, such as The Information, The Athletic, and even our very own Extra Crunch. If successful, the hope is that paid subscriptions will prove more sustainable and lucrative than advertising, which still dominates in media.

But Sur is purposely pacing herself when it comes to expenses in the early days. The team currently has only three full-time staff, including Sur, culture editor Imaan Sheikh and one full-time writer, Michaela Stone Cross.

Snigdha Sur, the founder of The Juggernaut.

“Sometimes at media companies people over-hire and over-promise, and then don’t deliver on the profitability or return,” she said. For this reason, The Juggernaut largely works with “freelancers who would probably never join any specific publication,” Sur said. While The Juggernaut hopes to have full-time staff writers eventually, the contributor approach helps temper spending.

Beyond pace, The Juggernaut is looking to build up its subscriber base by writing stories that require deep, creative thinking. The publication intentionally does not cover commoditized breaking news, which could have the potential to bring in more inbound traffic, or anything that doesn’t have a South Asian connection.

Sur is living the stories that she is working to tell. Born in Chhattisgarh, India, she grew up in the Bronx and Queens in New York City, and spent time living and working in Mumbai, India. Since founding The Juggernaut, her goal for the publication has been to be a place for not just South Asians, but for “anyone who has a form of curiosity and appreciation” for South Asian culture.

“We try not to translate words we don’t have to do, we’re not trying to dumb this down, we’re not trying to write for the white teen,” she said. “We’re trying to write for the smart, curious person. And we’re going to assume you know stuff.”

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Businesses reducing trash and plastic consumption are beginning to look like treasure to some VCs

Zuleyka Strasner didn’t set out to become an advocate for zero-waste consumption.

The former manager of partner operations at Felicis Ventures had initially pursued a career in politics in the U.K. before a move to San Francisco with her husband. It was on their honeymoon on a small island in the Caribbean that Strasner says she first saw the ways in which plastic use destroyed the environment.

That experience turned the onetime political operative into a zero-waste crusader — a transformation that culminated in the creation of Zero Grocery, a subscription-based grocery delivery service that sells all of its goods in zero-waste packaging.

Strasner returned from Corn Island with a purpose to reduce her plastic use, and found inspiration in the social media posts and work of women like Anamarie Shreeves, the founder of Fort NegritaLauren Singer, who became known for her TedX Teen talk on living waste free and launched Package Free; and Bea Johnson, who became a social media celebrity for her work reducing consumption and living waste-free.

Following in the zero-waste footsteps of others eventually led Strasner from her home in Redwood City, California to San Francisco’s Rainbow Grocery, a food co-op dedicated to sustainable business practices. That 45-minute drive and an hour spent in a store juggling jars, bottles and shakers to perform basic shopping tasks convinced Strasner that there had to be a better way to shop zero-waste — especially for busy parents, professionals and singles.

So she built one.

“I may have had no team and no money, but I had data. I spent 6 months alpha testing the early version of Zero. I was working from my apartment (cue cliché) getting real sign-ups, servicing real customers and doing a lot of growth hacking,” Strasner wrote in a post on Medium about the company’s early fundraising efforts. “It was really janky, but going between research reports, market data and the data I was collecting from real-people, I had something tangible to put under investors noses to back up how Zero looks at scale.”

Living through COVID-19 is a literal trash heap

Strasner’s push to create alternatives to single-use plastic in grocery delivery comes as the use of single use plastics skyrockets and grocery delivery services surge — putting her new company in the enviable position of solving an obvious problem that’s becoming more apparent to everyone.

An August study from the investment bank Jefferies on single-use plastic identified the surge in plastic use and laid the blame at the feet of the pandemic.

“Bans and taxes have been rolled back, physical and chemical recycling activity has decreased, and virus concerns may have reduced consumers’ desire to minimize consumption of single-use plastics,” said the report, entitled “Drowning in Plastics,” which was quoted in Fortune.

While much of the use in home delivery and consumer goods has been offset by reductions in the use of plastics in manufacturing as industries slowed down production, the reopening of international economies means there’s the potential for renewed industrial use even as consumers renew their love affair with plastic.

Companies like Strasner’s present a way forward for consumers willing to pay a premium for the waste reduction — and she’s not alone.

Changing the supply chain for food and consumer packaged goods

Lauren Singer was already two years into operating her (profitable and cash-flow positive since “day one”) Brooklyn-based and e-commerce stores when she raised $4.5 million for her plastic free and zero-waste wares last September.

The image of the years’ worth of waste she claimed to be able to fit into a single jar had made her a viral sensation on Instagram and she’d managed to turn that post, and her celebrity, into a business. She wasn’t alone. Bea Johnson, another star of the zero-waste movement, wrote the book on going zero-waste and has turned that into a business of her own.

At Package Free, products range from a line of plastic-free and zero-waste lifestyle products like bamboo toothbrushes and mason jars, to natural tooth powder alongside natural pacifiers, and a dog shampoo bar. The company’s packaging is composed of 100% up-cycled post-consumer boxes with paper wrapping and paper tape, according to the company.

Meanwhile, another New York-based startup, Fresh Bowl, raised $2.1 million in January to bring zero-waste packaging and circular economic principles to the bowl business. The company, founded by Zach Lawless, Chloe Vichot and Paul Christophe, uses vending machines around New York that can hold roughly 220 prepared meals with a five-day shelf-life. Those meals are distributed in reusable containers that customers can return for a refund of a deposit.

Before the pandemic hit in the early months of the company’s financing, each of its machines were on track to bring in $75,000 in revenue — and roughly 85% of the company’s containers were being returned for re-use, according to a January interview with chief executive officer Zach Lawless.

Roughly 40% of landfilled material is food or food packaging, Lawless said. “For consumers it’s hard to make that trade-off between convenience and sustainability,” he said. Companies like Fresh Bowl and Strasner’s Zero Grocery are each trying to make that tradeoff a little easier.

Designing a zero-waste delivery service

Zero Grocery currently counts around 850 unique items in stock and expects to be over 1,000 items at the end of the year — and all delivered in reusable or compostable packaging, according to Strasner.

“Our aim is to not create anything that would go into the landfill and really limit what would need to be recycled. For the products that are single use… they are banded toilet rolls and they’re wrapped in a single sheet of paper. It’s all compostable,” said Strasner. 

Zero Grocery’s current operations are confined to the Bay Area, but the company saw its growth triple when the pandemic hit in March and then grow 20X over the ensuing months, according to Strasner. And unlike companies like Singer’s and Lawless’, Strasner didn’t have the luxury of reaching out to a handful of investors for a small cap table.

“I have continuously raised throughout this period to get to this moment in time. Initially I believed that we would have a more typical round structure, maybe myself misunderstanding that I’m an atypical founder,” Strasner said. As a Black, trans woman, the path to “yes” from investors involved more than 250 pitches and an undue amount of “nos.” 

An early champion was Charles Hudson, the founder of Precursor Ventures, who helped lead a seed round for the company back in 2019. Hudson’s investment allowed the company to launch its first service, an exclusive, à la carte, home delivery service. It was basically Strasner wheeling a cart brimming with produce, grains and compostable items into customers’ homes and filling their own jars.

Zero Grocery chief executive Zuleyka Strasner on an early delivery run for her company. Image Credit: Zero Grocery

Ultimately untenable, the first service gave Strasner a view into the ways in which grocery delivery worked, and allowed her to create the second version of the service.

That was more like a latter-day milkman service, where the company would deliver next-day, door-to-door delivery of more than 100 zero-waste products. These were pre-packaged goods that the company just dropped off and then had customers return (a similar thesis to Fresh Bowl’s retail strategy).

That was around November 2019, when the company launched publicly across the Bay Area with a new offering. The initial traction allowed Strasner to raise another $500,000 from existing investors, as well as new firms like Chingona Ventures and Cleo Capital.

“At that point we had 60 members on the platform and had done four figures of revenue of that month,” Strasner said.

Then COVID-19 hit the Bay Area and sales started soaring. To meet the needs of a strained supply chain — since the company doesn’t use any third-party services for delivery and involves a heavy bit of sanitization of containers so they can be re-used — Zero Grocery raised another $700,00 from Incite.org, Gaingels, Arlan Hamilton and MaC Ventures.

As Strasner wrote in a Medium post:

When COVID-19 hit the US, our team was among the first companies to go into lockdown. By late February, only essential personnel were on the warehouse floor for order preparation and delivery in head-to-toe PPE. Soon after that, the Bay Area went into full shelter-in-place.

Much like other companies in the grocery delivery space, our demand skyrocketed. To keep up, we grew our team in half the time we anticipated and launched features that were half-baked. Customer experience is tantamount, and our underdog team fought tooth-and-nail to preserve that despite long hours, little sleep, and no time for planning. We abandoned our notions of roles and split up the responsibilities of customer service, order packing, feature development, and more.

Strasner’s experiences as an immigrant, Black, trans founder mean that she thinks about sustainability not just in environmental terms, but also social sustainability. That’s why she works with the staffing service R3 Score to provide opportunities for people who had criminal records. The service provides a risk analysis for employers of job applicants who have a criminal record, to give employers a better sense of their viability as an employee.

As she told Fast Company, “This is a highly capable, untapped labor force who is ready to work and is actively looking for opportunities… This is not merely a COVID stopgap measure for us; it’s something we’re incorporating into our business for the long-term.”

More money, fewer problems?

Zero Grocery now counts many thousands of customers on its service and has just raised another $3 million, led by the investment firm 1984, to grow the business. The company charges $25 for a membership that includes free deliveries and collects empty containers. Non-members pay a $7.99 delivery fee for groceries priced competitively with Whole Foods and other higher-end grocery options.

Right now, Zero Grocery operates as the only fully zero-waste online grocery store in the U.S., and its numbers are growing quickly.

But that kind of success can breed competition, and there are certainly no shortage of would-be competitors waiting in the wings.

Already some of the largest consumer packaged goods companies in the U.S. have rolled out a version of zero-waste delivery services for their products. These are companies like Procter & Gamble and Froneri, the owner of ice cream brand Häagen-Dazs (and others). In April, their reusable, no-waste delivery service Loop launched nationwide to provide customers across the country with recyclable and reusable packaged containers.

The commercialization of new kinds of packaging technologies from companies like NotPla, Varden and Vericool mean that compostable material packaging could become a wider solution to the waste dilemma.

Still, these solutions to packaging waste come with their own issues, like the sustainability of the supply chain used to make them and the carbon footprint of the manufacturing processes. In instances like these, reducing the need to manufacture new material is likely the most sustainable option.

And, in many cases, companies like Zero Grocery help their vendors do a lot of the work to reduce the footprint of their own supply chains.

“A lot of work is to enable them to exist within a plastic-free supply chain using our technology,” said Strasner, of the work she’d done with vendors. 

“I started Zero to make zero-waste grocery shopping effortless and empower people to protect the planet while shopping conveniently,” she said. That’s a notion everyone can treasure. 

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Founders can raise funding before launching a product

It’s possible to raise VC funding even if you haven’t built a real product, according to Charles Hudson, founder and managing partner at seed-stage firm Precursor Ventures. It’s just very, very difficult.

I interviewed Hudson during TechCrunch Early Stage, our virtual event for startup founders. He gave a short talk titled “How to sell an idea when you don’t have a product,” then answered questions from me and from attendees watching at home.

Hudson said Precursor invests in about 25 startups every year and that a majority are pre-launch and pre-traction. So when he’s considering startups where there “isn’t any evidence or traction,” he and other investors are basically considering two things: How well the founder knows the industry, and how well the investors know the founder.

Of course, if you’ve already had success and you know everyone on Sand Hill Road, it might not be that hard to get that first check. But what about everyone else?

Below, I’ve quoted some highlights from Hudson’s thoughts about how to raise money pre-product. You can also watch the full presentation/conversation at the end of this post.

‘You need to have a unique and durable insight that will still be true in 12 to 18 months’

You need to have a unique and durable insight that will still be true in 12 to 18 months … The unique part is important because you still haven’t launched your product yet. And so whatever it is that you’re doing, if it’s not unique, if it’s a really obvious insight, you’ll probably have 10 or 12 competitors that are launched in the market by the time you get your product out.

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Extension rounds help some startups play offense during COVID-19

The venture capital world is constantly changing, and its evolution can sometimes flip pieces of conventional wisdom on their heads. For example, a recent flurry of extension rounds from Silicon Valley’s hottest startups like Stripe and Robinhood seem to signal that the investment type has suddenly become cool.

Extensions evolving from unloved to hot is not the first time that a type of VC deal has gained, or lost luster. In past times, for example, raising consecutive rounds from the same lead investor was often perceived as a negative signal; why couldn’t the startup find a new, different lead investor? Today, in contrast, venture capitalists are using inside rounds to double-down on winning startups, a way of helping ensure returns for their own backers.

The recent phenomenon of extensions becoming vogue is a tale of the times, in which the best startups get to play offense, and startups that can’t show accelerating growth are left behind. Let’s explore what has changed.

A series of fortunate extensions

TechCrunch first wrote about the new extension-round trend after seeing what felt like a wave of the deals crop up. Some were large, like MariaDB’s huge $25 million add-on to its Series C, or Robinhood’s biblical $320 million addition to its Series F.

But most were smaller events like Sayari adding $2.5 million to its Series B, or CALA adding $3 million to its seed round. Even more recently, Eterneva raised another $3 million on top of its seed round, and also out this week was a million pounds more for Edinburgh-based Machine Labs’ seed round.

One reason for the growth of extension rounds in 2020 has been runway — making sure that a startup has enough. Upstarts often raise on an 18-month cadence. But because of COVID-19 and its constituent economic disruptions, many have reduced costs in a bid to bolster how long they have until their cash stores reach zero.

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Hear Charles Hudson explain how to sell an idea (without a product) at Early Stage

Startups often dance between selling dreams and building products, and we’ve enlisted the help of noted investor Charles Hudson to help founders sell an idea before they’ve built a product. Hudson is speaking at TechCrunch’s inaugural virtual event, TechCrunch Early Stage. The two-day event runs July 21 and 22 and will feature sessions targeting all aspects of building a startup.

Hudson has seen a lot of startups over his career as an investor and knows what it takes to sell an idea when there isn’t yet a product. As he’ll explain, this is often a tough skill to learn, and it takes practice to craft the correct message that shows obtainable goals while putting the investor at ease.

Charles Hudson is a managing partner at Precursor Ventures, where he focuses on pre-seed investments in companies building B2B and B2C software applications. Before this role, he was an investor at Uncork Capital (formerly SoftTech VC) and In-Q-Tel, the VC arm of the U.S.’s Central Intelligence Agency. Along the way, he’s held various executive and board positions at startups and organizations.

Hudson’s session at TC Early Stage is a must-watch for early-stage founders. Startups begin as an idea, and often that idea needs funds to turn into a product. Hudson will help show founders how to get an investor to buy into the concept before the product is built.

TC Early Stage takes place over two days in July and features 50+ experts across startup core competencies, such as fundraising, operations and marketing. The virtual event features some of the best operators, investors and founders in the startup world. Hear from Ann Miura-Ko on how to find a product-market fit. Ali Partovi is set to talk about how to hire early engineers, and Caryn Marooney’s session will explore how to make your brand stand out.

What’s more, most of the speakers, who happen to be investors, are participating in TechCrunch’s CrunchMatch, our program that connects founders to investors based on shared interests.

Here’s the fine print. Each of the 50+ breakout sessions is limited to around 100 attendees. We expect a lot more attendees, of course, so signups for each session are on a first-come, first-serve basis.

Buy your ticket today, and you can sign up for the breakouts we are announcing today, as well as those already published. Pass holders will also receive 24-hour advance notice before we announce the next batch. (And yes, you can “drop” a breakout session in favor of a new one, in the event there is a schedule conflict.) 

Get your TC Early Stage pass today and jump into the inside track on the sessions we announced today, as well as the ones to be published in the coming days.

Possible sponsor? Hit us up right here.

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Precursor Ventures’ Charles Hudson on ‘the conversation no one has during an upmarket’

For pre-seed startups, precarious times are baseline until they secure their first customer, first hire and first check. But no matter how built-in turbulence might be for a pre-seed founder, we’re entering a period where stresses are amplified and outlooks are unpredictable.

In light of the new market conditions, a harder fundraising market and slower expected growth, Charles Hudson (founder and general partner of Precursor Ventures) is urging his portfolio companies to reassess their futures with a refreshingly human question: “Are you excited and prepared to run this company for the next two years?

If not, you might want to do something else. Why? Because if a super early-stage company manages to survive the COVID-19 era, making it out the other end, it’s not clear that they’ll be venture-ready when markets recover. As Hudson put it, “there’s never been a better time to maybe fold.” That’s because, he explained, startups that merely survive won’t be judged merely against their peers that also survived; they will also compete with brand-new startups for capital and companies that didn’t need to hunker down during lean times.

It’s possible to make it through, but it won’t be an easy path.

TechCrunch spoke with Hudson earlier this week as part of our ongoing Extra Crunch Live series that brings leading founders and investors to our (virtual) stage. Between our editors and journalists and the best questions from the audience, we’re working with guests to understand the new world that we find ourselves in. That we’re hosting these events virtually instead of in-person is testament to our changed reality.

But the chat was far from all gloom; Hudson is bullish on a number of things. Niche publications with subscription economics? Yes. Social services targeting particular audiences? Yep! Precursor is still cutting checks into net-new deals, and while it’s wrapping up its second main fund and first opportunity fund, the firm is also raising a new, larger capital pool.

The conversation ran the full hour we had set aside for it, meaning we had to condense some later discussions about fintech and the new trade-off between growth and profit, but we did get to diversity in venture and startups in the future, and what impact a recession might have on both (it’s a bigger possible impact than you’re considering).

Hit the jump for the best Hudson takeaways and the full audio recording from the session. Head here if you need Extra Crunch access; there are some trials for just a few bucks, so everyone can access the chat. Let’s go!

Raising a fund in the COVID-19 era

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Extra Crunch Live: Join Charles Hudson for a look at today’s seed-stage landscape right now

Earlier this week, we kicked off our Extra Crunch Live series with an interesting chat with Cowboy’s Aileen Lee and Ted Wang. Today, we will be back at 3 p.m. PST/6 p.m. EST/10 p.m. GMT with a new guest: Charles Hudson, the general partner of Precursor Ventures.

Extra Crunch members will find an AddEvent link below to drop the details directly into their calendar and folks who want to participate directly can hit up the Zoom link (also below). We’ll ask as many audience questions as we can, so please make them sharp — no pitches, please.

Charles Hudson founded Precursor Ventures to invest in pre-seed and seed-stage companies. Earlier this year, the firm filed paperwork to put together a $40 million third fund after previously raising two main funds and one $10 million “opportunity” fund.

As we await hard and accurate numbers on how COVID-19 is impacting fundraising, we’ll ask Hudson to walk us through the changes he has seen and will cover some basics: The best way to pitch him, what his to-do list looks like these days and if the pandemic has made Precursor newly bullish or bearish on certain sectors.

Then, we’ll get much nerdier: Will we see the number of party rounds fall further now that it’s harder to gather investors in real life? Do you think we’ll see pre-seed raises ask for more ownership terms? And what is the latest with the wacky world of early-stage valuations?

There’s a lot to talk about. And we haven’t even mentioned YC’s pro rata change yet.

After Hudson, we have a stacked lineup of Extra Crunch live guests, including Mitch and Freada Kapor, Mark Cuban, Roelof Botha and Kirsten Green, with more to be announced soon.

You can find information below with details for joining today’s discussion, as well as an AddEvent link to put the details directly onto your calendar.

Sign up for Extra Crunch to get access to all these episodes where you can view the talks live, participate in the Q&A with industry leaders and watch later on-demand if you can’t make the live timing. You can also see the chat via YouTube below. Talk soon!

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Pepper’s bra wants to solve the woes of small-chested women

Ask any woman and she will tell you that most of her bras do not fit her optimally. In fact, a majority of women end up wearing the wrong size. A large part of the problem is that sizing is standardized, unlike women’s bodies. With every passing year, more people are also shopping online, meaning fewer opportunities to actually try on bras — a trend that’s only accelerating given the shutdown the world is experiencing right now.

One particular problem, and a widespread one, according to entrepreneurs Jaclyn Fu and Lia Winograd, is that bras are generally too big for small-chested women. It’s the reason the former co-workers came together to found Pepper, a three-year-old, Denver-based startup that’s expressly focused on creating bras that fit smaller cup sizes.

As Fu explains it, most bra companies use a size, say 36C, then apply that same design to other bra sizes, like a 32A. While the step is logistically sound — applying a standard base design to other sizes — it doesn’t translate well into actual fit.

“It means a person who is a 32A is wearing a design that was intended for a 36C, causing fit issues like cup gaps,” says Fu.

Usually, women try to resolve the problem by tightening their bra straps or changing sizes, but Pepper’s solution is to create its own, smaller cup molds from a factory in Medellin, Colombia, where Winograd grew up.

Fu made the first prototype for Pepper based on her own chest size. Since then, she’s gone to customers’ houses to conduct fittings and research. Beyond cup size, Pepper also addresses underwire woes, making its products less curved and shorter to follow the natural size of a smaller-chested woman.

To increase customer engagement, Pepper started virtual one-to-one fit sessions for customers who are buying a bra online for the first time, and like other companies has a “fit quiz” for people to take online, too.

Pepper now sells a wide variety of sizes, all the way from from 30A to 38B, and prices range from $48 to $54.

Pepper certainly isn’t the only startup trying to fit into the bra industry. Companies like Kala, SlickChicks and ThirdLove all tout comfort and inclusivity in sizing and fitting.

The biggest of the three is ThirdLove, a San Francisco DTC bra and underwear company that has raised $68.6 million in known venture capital to date, per Crunchbase. ThirdLove brands itself as a brand that sells a “bra for every body” with inclusive sizes, and is now expanding into retail, international markets and swim and athletic wear. The company was last valued at more than $750 million.

It’s unclear how many new brands the market can support, or that can survive this pandemic. Even companies with meaningful market share and fresh capital are struggling to stay afloat as shoppers reduce their spend right now. Earlier this month, ThirdLove laid off 30% of its staff, citing COVID-19’s impact on business.

Even still, Pepper’s founders remain optimistic. Pepper’s Kickstarter $10,000 launch campaign — staged in 2017 — was separately funded in less than 10 hours, Fu notes.

The success of that campaign just helped the company secure $2 million in seed funding from investors, including Precursor Ventures, New York University Innovation Fund and Denver Angels. Others participating include the co-founder of MyFitnessPal, Albert Lee.

Fu adds that the company, which employs three people, is “close to profitability” on a $3 million revenue run rate. In 2019, most of its sales came directly from consumers on their site — a good sign that its growth ties to user loyalty versus relying on partnerships with retailers.

The nuance of buying a bra has long been an in-person ordeal. But now, because of COVID-19’s spread and the resulting shut down of many brick-and-mortar stores, those who need a new bra might have to turn online for the very first time. It’s an opportunity for companies like Pepper to prove that they can master fit without measuring tape and a changing room.

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Raising VC in Silicon Valley as a female POC

Nathan Beckord
Contributor

Nathan Beckord is CEO of Foundersuite.com, a software platform for raising capital and managing investors that has helped entrepreneurs raise over $2 billion since 2016. He is also the host of Foundersuite’s How I Raised It podcast.

As the world grows increasingly digital, the craving for face-to-face connections is surging. Squad, an invite-only community and app, is trying to fill the need for offline connections by curating tight-knit events for Gen Z and Millennials.

“It mimics building relationships in real life,” says founder and CEO Isa Watson.

It’s an idea that investors are already backing: Squad closed a $3.5 million seed round and plans to raise its Series A in early 2020, but the road to securing that round was anything but easy. During a conversation on the How I Raised It podcast, Watson shared the ups and downs of her unique path to fundraising.

Establish credibility for a few years before fundraising

She started by putting some of the earliest capital into the business herself with support from her family. She then worked her way through more than 200 meetings in Silicon Valley to build up her credibility as a founder — a step that she can’t stress enough — before Squad even started its official seed round.

“Despite the fact that I went to MIT, despite the fact that I managed a billion-dollar product at JPMorgan Chase and even built a huge digital product, I was still a Silicon Valley outsider,” Watson says.

People sometimes have the perception that being an alumni at a top U.S. university will mean they can go to Silicon Valley and just be “in,” Watson explains, but that’s not quite how it works.

“It takes a lot of work and a lot of credibility building,” she says. “That’s what I was doing for a few years before we actually did our official seed round. By the time I did it, it was like my reputation preceded me and there was enough familiarity with me.”

isa watson squad ceo

Isa Watson, Squad founder and CEO

Don’t do the cold outreach thing — warm introductions only

Despite taking more than 200 meetings in her efforts to crack Silicon Valley, Watson never took a cold meeting.

“Cold outreach is a tactic that I see a lot of founders using,” she says, “whereas I would argue that the more effective introduction comes from someone who knows someone.”

Leveraging the connections she built was critical in connecting Watson to her eventual funders. “They’re all referring you to the next three people to talk to,” Watson says. “It becomes like tree branches and then a network that’s growing in a multiplicative fashion.”

One of Squad’s earliest investors was Steven Aldrich, who at the time was working as chief product officer at GoDaddy . Both Aldrich and Watson grew up in North Carolina, and Steven’s father shared hometown roots with her, which helped her make the initial connection.

“It was about consistently making connections like that,” she says. “Steven introduced me to three people, and then those three other people introduced me to two people. And that’s essentially how I got the ball rolling.”

Not all meetings need to be about meeting for coffees or lunches, either — Watson took plenty of calls while expanding her network, as well. But the important step was making those connections, which was “a really hard hustle and grind, head down,” for the first two years.

Be really specific when asking for advice

When meeting people in Silicon Valley or expanding her network of prospective funders, Watson didn’t tease future funding rounds or send off vague meeting requests.

In trying to build out her network, she first researched a couple of key things: who did she need to know in order to build a really strong product, and who did she need to know in order to have solid distribution or growth marketing? Once she identified those folks, she would reach out to them individually and ask them for specific advice in their area of expertise.

“People always say, ‘When you want money, ask for advice. If you want advice, ask for money,’” Watson says. “Being super-explicit in the ask and explaining how you’ll spend their time and their brain space is super important.” No one has time for a generic request like, “Hey, can I pick your brain?”

When you’ve connected with someone, you should always ask them for recommendations for experts in specific areas — like growth marketing, product, etc. If they volunteer a few names, ask if you can send an email that they could forward on to introduce you to those individuals.

Following the introductions, it’s important to remember that it’s not just a “one and done,” as she says. Once you’ve met with someone through an introduction, follow up: let them know how the meetings went and thank them again.

“It’s like really, really intense relationship management, and it’s something that people with the highest EQ do best,” says Watson. “I would identify my needs, make specific asks … and then I would make sure to explicitly ask if they did not offer for three other intros for people that could be helpful, that would be excited about what we’re doing.”

Secret weapon: your fundraising quarterback

When she realized it was time to start raising money for Squad, her first move was to identify her “quarterback for fundraising” — in this case, Charles Hudson from Precursor Ventures. It’s helpful, according to Watson, to not have “too many cooks in the kitchen,” or else you’ll end up with far too many opinions that don’t align.

Hudson had already invested a small amount of money in Squad at the time, but he quickly became the person Watson went to for feedback on her pitches. He counseled her on other aspects of running a process.

“One thing Charles tells me is that, with fundraising, you’re likely only going to be successful if that’s your core focus at that time,” Watson says. “It’s not something you can do passively.”

So Hudson and Watson sat down and came up with a list of 35 target venture capitalists. He introduced her to five who she didn’t expect to be a good fit. They first went with the ones they didn’t expect would be a perfect match so she could gather feedback and see if Squad was actually ready to raise capital.

Of those first five meetings, one or two “were complete dings” and turned Squad down outright — but Watson made it to partner meetings in the three other meetings, a sign that VCs were seriously considering Squad.

Based on that feedback, Hudson introduced Watson to 10 more VCs — and shortly after, she met Michael Dearing at Harrison Metal, who led Squad’s seed round.

Choose your seed funders carefully

After Dearing offered up a term sheet of $3 million, Watson quickly had offers from other VCs.

“It’s funny because it took me deliberately being in the market for fundraising for like two and a half months to get that ‘yes’ from Michael. Before that, I had no cash really committed,” she says. “And then after just a few days of letting people know I had a term sheet for $3 million, I had like $6 million on a table. VCs are such followers.”

With that many offers on the table following Dearing’s lead, Watson was in the enviable position of needing to pick who she’d let into the seed round. So how did she choose?

“The first thing is value add,” Watson says. She asked herself: “did I feel like I had the right assortment of value? I maybe want someone in there who’s really strong on product; I may want someone who’s really strong at growth, strong at marketing.”

Her second criteria for making the decision was a less resume-focused. Simply put, she went with her gut.

“One thing that founders really, really underestimate is — is this person a good human being? I went with the people that I had felt most comfortable with, the people who I felt I could trust based on my interactions with them, and who were just supportive along the way.”

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