How to pick the right Series A investors

Early-stage startup founders who are embarking on a Series A fundraising round should consider this: their relationship with the members of their board might last longer than the average American marriage.

In other words, who invests in a startup matters as much — or more — than the total capital they’re bringing with them.

It’s important for founders to get to know the people coming onto their board because they’ll likely be a part of the company for a long time, and it’s really hard to fire them, Jake Saper of Emergence Capital noted during TechCrunch’s virtual Early Stage event in July. But forging a connection isn’t as easy as one might think, Saper added.

The fundraising process requires founders to pack in meetings with numerous investors before making a decision in a short period of time. “Neither party really gets to know the other well enough to know if this is a relationship they want to enter into,” Saper said.

“You want to work with people who give you energy,” he added. “And this is why I strongly encourage you to start to get to know potential Series A leads shortly after you close your seed round.”

Here are the best methods to meet, win over and select Series A investors.

Identify industry experts

Saper recommends extending the typically short Series A time frame by identifying a handful of potential leads as soon as a founder has closed their seed round. Founders shouldn’t just pick any one with a big name and impressive fund. Instead, he recommends focusing on investors who are suited to their startup’s business category or industry.

The story behind Rent the Runway’s first check

When Rent the Runway co-founders Jennifer Fleiss and Jennifer Hyman got their first term sheet, it had an exploding clause in it: If they didn’t sign the offer in 24 hours, they would lose the deal.

The co-founders, then students at Harvard Business School, were ready to commit, but their lawyer advised them to pause and attend the meetings they had previously set up with other investors.

Twelve years later, Rent the Runway has raised $380 million in venture capital equity funding from top investors like Alibaba’s Jack Ma, Temasek, Fidelity, Highland Capital Partners and T. Rowe Capital. Fleiss gave up an operational role in the company to a board seat in 2017, as the company reportedly was eyeing an IPO.

But the shoe didn’t always fit: Earlier this year, Rent the Runway struggled with supply chain issues that left customers disgruntled. Then, the pandemic threatened the market of luxury wear more broadly: Who needs a ball gown while Zooming from home? In early March, the business went through a restructuring and laid off nearly half of its workforce, including every retail employee at its physical locations.

In 2009, Fleiss and Hyman were successful Harvard Business School students. Hyman’s father knew a prominent lawyer who agreed to advise them on a contingency basis in exchange for connecting them with potential investors.

Still, fundraising “was extremely hard,” Hyman said. “We were in the middle of a recession and we were two young women at business school who had never really done anything before.”

Fleiss said venture capital firms often sent junior associates, receptionists and assistants to take the meeting instead of dispatching a full-time partner. “It was clear they weren’t taking us very seriously,” Fleiss said, recounting that on one occasion, a male investor called his wife and daughter on speaker to vet their thoughts.

In an attempt to test their thesis that women would pay to rent (and return) luxury clothing, Fleiss and Hyman started doing trunk pop-up shows with 100 dresses. On one occasion, they rented out a Harvard undergraduate dorm room common hall and invited sororities, student activity organizations and a handful of investors.

Only one person showed up, said Fleiss: A guy “who was 30 years older than anyone else in the room.”

Old-fashioned meets nontraditional

SaaS securitization will disrupt VC’s biggest returns this coming decade

SaaS investing has been on fire the past decade and the returns have been gushing in, with IPOs like Datadog, direct listings like Slack and acquisitions like Qualtrics (which is now being spun back out) creating billions of wealth and VC returns. Dozens more SaaS startups are on deck to head toward their exits in the same way, and many VC funds — particularly those with deep portfolios in the SaaS space — are going to perform well.

Yet, the gargantuan returns we are seeing today for SaaS portfolios are unlikely to repeat themselves.

The big threat in the short term is simply price: SaaS investing has gotten a lot more expensive. It may be hard to remember, but just a decade ago the business model of “Software as a Service” was revolutionary. Much in the way that it took years for cloud infrastructure to take hold in corporate IT departments, the idea that one didn’t license software but paid by user or by usage over time was almost heretical.

For VCs willing to make the leap into the space, prices were (relatively) cheap. Investor attention a decade ago was intensely centered on consumer web and mobile, driven by Facebook’s blockbuster IPO in May 2012 and Twitter’s IPO the following year. While every investor was chasing deals like Snap(chat), the smaller population of investors targeting enterprise SaaS (or even more exotic spaces like, gulp, fintech) got great deals on what would later become the decade’s biggest unicorns.

Extra Crunch Live: Join our Q&A tomorrow at noon PDT with Y Combinator’s Geoff Ralston

From Airbnb to Zapier, and Coinbase to Instacart, many of the tech world’s most valuable companies spent their earliest days in Y Combinator’s accelerator program.

Steering the ship at Y Combinator today is its president, Geoff Ralston . We’re excited to share that Ralston will be joining us on Extra Crunch Live tomorrow at noon pacific.

Extra Crunch Live is our virtual speaker series, with each session packed with insight and guidance from the top investors, leaders and founders. This live Q&A is exclusive to Extra Crunch members, so be sure to sign up for a membership here.

Ralston took on the YC President role a little over a year ago shortly after Sam Altman stepped away to focus on OpenAI.

In the months since, Y Combinator has had to reimagine much about the way it operates; as the pandemic spread around the world, YC (like many organizations) has had to figure out how to work together while far apart. In the earliest weeks of the pandemic, this meant quickly shifting their otherwise in-person demo day online; later, it meant adapting the entire accelerator program to be completely remote.

While still relatively new to the president seat, Ralston is by no means new to YC. He joined the accelerator as a partner in 2012, and his edtech-focused accelerator Imagine K12 was fully merged into YC’s operations in 2016.

How to time your Series A fundraise

When founders start fundraising is as important as how they make their pitch to investors.

Timing matters and it’s more complicated than founders might realize, but it’s not just about picking the right month or time of day. Finding the right time to fundraise requires a micro- and macro-level strategy, according to Jake Saper of Emergence Capital, who joined TechCrunch’s virtual Early Stage event last week.

“There are really two angles to think about,” Saper said. The first is the macro perspective that takes into account the general flow of deals in the industry. Then there’s the micro timing that is specific — and different — for every startup, he added.

While Saper was particularly focused on giving advice to startup founders who have already raised a seed round and are preparing to raise a Series A, he said that most of his guidance can be applied to companies at a variety of funding stages. Let’s get started with the basics.

Peak pitch deck

The reality is that founders fundraise in all times of the year. However, there are certain times of the year when investors are more actively reviewing pitch decks.

January and February, followed by September, are the most active months for investors, based on data from DocSend that measured visits per pitch deck sent out by entrepreneurs each month.

Emergence Capital pitch deck data Early Stage

Image Credits: Jake Saper/Emergence Capital

This fits with Emergence’s anecdotal evidence. The firm sees founders who spend a lot of December preparing for a big launch or fundraise in January and February, Saper said. By the time founders begin sending decks out in January, VCs are back from holiday vacations or other tech-related events, like CES. The same rhythm begins in summer with founders using these months to prep for fundraising in the fall.

While this is a common time to pitch VCs, keep in mind that you’re also fighting for their attention, Saper said.

Six things venture capitalists are looking for in your pitch

Founders pitch venture capitalists at every available chance, which is why most of them quickly develop the skills required to identify whether someone is offering them an opportunity or wasting their time.

At TechCrunch Early Stage, I chatted with NFX Managing Partner James Currier about how founders can find the right investors and what they need to show to win an investment. Currier has been on both sides of the deal table and founded several startups before devoting himself to early-stage investing, where he has backed companies like Lyft, Houzz and Houseparty .

“One of the ways that investors are similar is that whenever they look at all the companies coming to them, most of them get into a quick ‘no’ situation, some of them get into the ‘maybe’ and very few get into the quick ‘yes,’ ” Currier says.

He shared six reasons investors might give a founder the rare and highly coveted “quick yes,” an effort to lock down a deal that’s either perfect for them or too enticing to pass up. Realizing what exactly investors are seeking can help founders understand how to pitch at the first meeting and what they should leave for follow-ups. For those who couldn’t virtually attend TechCrunch Early Stage, check out the link below.

This interview has been lightly edited for clarity. 

1. Traction

“So the first thing that they’re looking for is traction. Look, even if they don’t like you, if they don’t like the market, but you’re making a ton of money, what are they going to say? Like if it’s growing really quickly and you’re profitable, you’ve got high margins and everyone wants to work for you, and there’s this buzz around you. What are they going to say? They’re gonna have to invest because you’ve got traction.”

Lo Toney’s product manager playbook for pitch deck success

The cold email worked — you’ve landed a meeting with your dream investor. Hell, you even set aside $40,000 for a pitch deck consultant to make sure your presentation looks suave.

One thing to figure out before you pick out a Zoom background: what information actually goes into those slides?

Lo Toney, founding managing partner at Plexo Capital, has advice for founders looking to raise money: think like a product manager while crafting your pitch deck. Toney has helped shape products at Zynga, Nike and eBay, and currently serves as both a GP and an LP at Plexo Capital, which invests in funds and startups. He’s done a ton of pitching and gotten pitched himself, which is why we invited him to TechCrunch Early Stage 2020.

“The framework of product management is very similar to the same playbook used by an early-stage investor and early-stage investors in the absence of an abundance of data,” Toney said. “They’re really thinking very similar to a product manager to evaluate an opportunity.”

Crafting a solid pitch deck is critical to the success of a startup seeking venture capital. Investors, however, spend less than four minutes on average per deck, and some even tell you that you have half that much time (so either talk fast or pick your favorite slides). Even if you have the business to prove that you’re the next Stripe, if you butcher the story behind the numbers, you could lose the potential to get the capital you need.

Toney said adopting a product manager mindset helps refine what that story looks and feels like.

“The story is not your product. It’s not your company, and it’s not the entrepreneur. It’s how your customer’s world is going to be better when your product has solved their problem,” he said, quoting Rick Klau from GV.

In action, Toney broke down the framework into four key slides: problem, market, solution and, of course, team.

Problem

First up, most investors say they want to see the problem you’re trying to solve up high. Toney is no different.

“I like to see an entrepreneur describing the desired outcome first, and then what are some of those roadblocks that come along the way to that desired outcome?” he asked. Similar to a product manager, founders could illustrate the different challenges that could come to executing a solution on a specific problem.

Watch the first TechCrunch Early Stage ‘Pitch Deck Teardown’

Have you ever taken something apart, like a clock or a motor?

The method is particularly useful when it comes to learning how things work — or how they don’t, in some cases.

During TechCrunch’s Early Stage event, two venture capitalists took pitch decks and evaluated them with a critical eye on content, presentation and overall messaging. If you missed it the first time through, watch it below in its entirety.

The session was a blast. This was the first time we’ve hosted this event, but we’re working on bringing this session to TechCrunch’s main event, Disrupt, this September.

Accel’s Amy Saper and Bessemer’s Talia Goldberg gave great advice as we clicked through each deck. First impressions are everything, and pitch decks are often the first glimpse of companies by potential investors and business partners. It’s critical that these decks properly present and illustrate in a concise and effective manner the goals and potential of a company.

Ann Miura-Ko’s framework for building a startup

As an early-stage investor, Floodgate’s Ann Miura-Ko looks for two breakthroughs in order to invest in a startup: The first happens in the value-seeking stage of a startup’s journey and the second occurs in its growth-seeking phase.

“There are really two stages to building a company,” Miura-Ko said at the TechCrunch Early Stage virtual event earlier this week. “One is what we call value-seeking mode, and this is where you’re really trying to figure out what the company actually looks like, including what’s the product? Who are you selling to? How do you price it? All of these things are still being discovered in the value-seeking mode.”

After founders have answered those questions, they can move into growth-seeking mode, she said. That’s the point when startups are trying to attract as many customers as possible.

Throughout these two distinct stages, Miura-Ko says she looks for the two breakthroughs: the inflection insight and product-market fit.

Inflection insights

The idea of an inflection insight, Miura-Ko said, is a relatively new framework Floodgate is exploring. Often times, she said founders need to ride some massive, exponential curves that allow their businesses to grow sustainably and scale.

These inflections have two parts to it: cause and impact. The causes are generally either technological (cloud, 5G), regulatory (GDPR, AV regulation) or societal (belief or behavior shifts). On the impact side, products and distribution may become cheaper or faster, while also presenting new use cases or customers, she said.

“Or even more interesting, you have something that was impossible that now is possible,” she said. “And that is an exponential impact that you could ride on.”

But simply finding that inflection insight doesn’t mean you should create a business. What founders must do next is determine if the insight is right and nonconsensus.

A recapitalization reckoning

If you’re an angel who invested in a startup that was meant to go public in 2014, you might be getting a little bit impatient. High-risk, high-reward investing has lost its shine in this environment: the stock market is a mess these days, and you want your cash back.

Enter recapitalization events, where startups restructure their entire cap table to squeeze out old investors, bring on new ones and shift the way equity and debt is managed. For investors, it’s a killer way to enter a company on friendlier terms than normal (read: desperation), and a nice way to get liquidity on a startup you’re betting on.

For founders, it’s rarely good news, as departing investors is not a metric they’re going to add to the pitch deck. As one investor said on background, the spur of coronavirus-related recapitalization events shows “hella dilution for desperate times.”

That’s what makes Workhuman’s transparency with its recent recapitalization event all the more enticing.

Last year, the human-resources platform brought in $580 million in revenue from customers like LinkedIn, Cisco, J&J and other clients. In April, business grew 40%. Co-founder and CEO Eric Mosley says business has grown five times in size since the company pulled back from its 2014 plans to IPO. Workhuman hasn’t raised a single venture round since 2004 (and doesn’t plan to any time soon).

Being conservative has paid off; although Workhuman has operated for nearly two decades, Mosley says he thinks the company is still at the “tip of the iceberg.” The company recently had a recapitalization event to sell the stakes of its earliest investors, who cut a $200,000 check more than 20 years ago.