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May Mobility’s Edwin Olson and Nina Grooms Lee and Toyota AI Ventures’ Jim Adler on validating your startup idea
When a founder has a work history that includes the name of the parent company of one of their key investors, you probably assume that was one of the first deals to come together. Not so with May Mobility and Toyota AI Ventures, which connected for the company’s second seed round, after May went out and raised its original seed purely on the strength of its own ideas and proposed solutions.
That’s one of the many interesting things we learned from speaking to May Mobility co-founder and CEO Edwin Olson, as well as Chief Product Officer Nina Grooms Lee and Toyota AI Ventures founding partner Jim Adler on an episode of Extra Crunch Live.
Extra Crunch Live goes down every Wednesday at 3 p.m. EDT/noon PDT. Our next episode is with Sequoia’s Shaun Maguire and Vise’s Samir Vasavada, and you can check out the upcoming schedule right here.
Meanwhile, read on for highlights from our chat with Olson, Grooms Lee and Adler, and then stay tuned at the end for a recording of the full session, including our live pitch-off.
A different approach to corporate VC
One thing Adler brought up early in the chat is that Toyota AI Ventures likely takes a different approach than most traditional corporate VCs, which are often thought of as being more incentivized by strategic alignment than by venture-scale returns. Adler says the firm he founded within the automaker’s corporate umbrella actually does behave much more like a traditional VC in some ways than many would assume.
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CEO Manish Chandra and investor Navin Chaddha explain why Poshmark’s Series A deck sings
Mayfield partner Navin Chaddha and Poshmark founder and CEO Manish Chandra met all the way back in 2003, well before Poshmark was even a glimmer in his eye. They stayed connected over the years, through Chandra’s sale of his startup Kaboodle to Hearst and after he left.
At a breakfast one morning, Chandra told Chaddha he was going to try to do everything from his iPhone for the next six months.
Over the course of that time, the idea for Poshmark started to percolate into something more concrete. Chandra, following Kaboodle, knew he wanted to do several things differently. The first was create an engagement and revenue model that was symbiotic, rather than starting with engagement and having to build out a business model later. He also knew he wanted to start with people first, and build a founding team that had deep DNA in the fashion world to pair with his technical background.
He met Tracy Sun, brought her on, and got to work.
This was back in 2011, and Chandra was absolutely adamant that he wanted Poshmark to be an app, not a website. So adamant, in fact, that during beta he actually provided 100 users with video iPods. (He recalled that he only got 20% of them back.)
“Lead with love, and the money comes.” It’s one of the cornerstone values at Poshmark. The company practiced that early on by holding IRL, and then virtual, parties, allowing users to show each other their wares and create an engagement cycle that offered instant gratification. The user base grew from 100 to 150 to 1,000 and so on.
“We still to this day use a similar kind of strategy in a much more compressed timeframe as we go to different countries,” said Chandra. “We focus on building the community first and then scale that community.”
Chaddha and Mayfield led the company’s Series A deal a decade ago. On the latest episode of Extra Crunch Live, Chandra and Chaddha sat down with us and walked us through that original Series A pitch deck (which you can check out below). They also participated in the Pitch Deck Teardown, giving their expert feedback on decks submitted by the audience. If you’d like your deck to be featured on a future episode of Extra Crunch Live, hit up this link.
Poshmark’s Series A Deck
Time stamp — 11:00
Poshmark was built on a couple fundamental premises. The first was that the iPhone would transform the way we do just about everything. The second was more pointed: That fashion, at the time underserved by technology, was a discovery process over a direct search process. A decade ago, Chandra envisioned a fashion marketplace that mimicked shopping in the real world — walk into a shop and let natural attraction do its thing — without holding any inventory.
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Ironclad’s Jason Boehmig: The objective of pricing is to become less wrong over time
In 2017, Ironclad founder and CEO Jason Boehmig was looking to raise a Series A. As a former lawyer, Boehmig had a specific process for fundraising and an ultimate goal of finding the right investors for his company.
Part of Boehmig’s process was to ask people in the San Francisco Bay Area about their favorite place to work. Many praised RelateIQ, a company founded by Steve Loughlin who had sold it to Salesforce for $390 million and was brand new to venture at the time.
“I wanted to meet Steve and had kind of put two and two together,” said Boehmig. “I was like, ‘There’s this founder I’ve been meaning to connect with anyways, just to pick his brain, about how to build a great company, and he also just became an investor.’”
On this week’s Extra Crunch Live, the duo discussed how the Ironclad pitch excited Loughlin about leading the round. (So excited, in fact, he signed paperwork in the hospital on the same day his child was born.) They also discussed how they’ve managed to build trust by working through disagreements and the challenges of pricing and packaging enterprise products.
As with every episode of Extra Crunch Live, they also gave feedback on pitch decks submitted by the audience. (If you’d like to see your deck featured on a future episode, send it to us using this form.)
We record Extra Crunch Live every Wednesday at 12 p.m. PST/3 p.m. EST/8 p.m. GMT. You can see our past episodes here and check out the March slate right here.
Episode breakdown:
- The pitch — 2:30
- How they operate — 23:00
- The problem of pricing — 29:00
- Pitch deck teardown — 35:00
The pitch
When Boehmig came in to pitch Accel, Loughlin remembers feeling ambivalent. He had heard about the company and knew a former lawyer was coming in to pitch a legal tech company. He also trusted the reference who had introduced him to Boehmig, and thought, “I’ll take the meeting.”
Then, Boehmig dove into the pitch. The company had about a dozen customers that were excited about the product, and a few who were expanding use of the product across the organization, but it wasn’t until the ultimate vision of Ironclad was teased that Loughlin perked up.
Loughlin realized that the contract can be seen as a core object that could be used to collaborate horizontally across the enterprise.
“That was when the lightbulb went off and I realized this is actually much bigger,” said Loughlin. “This is not a legal tech company. This is core horizontal enterprise collaboration in one of the areas that has not been solved yet, where there is no great software yet for legal departments to collaborate with their counterparts.”
He listed all the software that those same counterparts had to let them collaborate: Salesforce, Marketo, Zendesk. Any investor would be excited to hear that a potential portfolio company could match the likes of those behemoths. Loughlin was hooked.
“There was a slide that I’m guessing Jason didn’t think much of, as it was just the data around the business, but I got pretty excited about it,” said Loughlin. “It said, for every legal user Ironclad added, they added nine other users from departments like sales, marketing, customer service, etc. It was evidence that this theory of collaboration could be true at scale.”
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Felicis’ Aydin Senkut and Guideline’s Kevin Busque on the value of simple pitch decks
Even though Kevin Busque is a co-founder of TaskRabbit, he didn’t get the response he was hoping for the first time he pitched his new venture to Felicis Ventures’ Aydin Senkut. Nonetheless, he said the outcome was one of the best things that could have happened.
“I’m kind of glad that he didn’t invest at the time because it really forced me to take a hard look at what we were doing and really enabled us to become Guideline,” said Busque. “That seed round was an absolute slog. I think I spent seven or eight months trying to raise a round for a product that didn’t exist, going purely on vision.”
Eventually, that idea evolved into Guideline, which describes itself as “a full-service, full-stack 401(k) plan” for small businesses. Eventually, Senkut did write a check — Felicis led Guideline’s $15 million Series B round. Today, Guideline has more than 16,000 businesses across 60+ cities, with more than $3.2 billion in assets under management. The company has raised nearly $140 million.
This week on Extra Crunch Live, Busque and Senkut discussed Guideline’s Series B pitch deck — which Senkut described as a “role model” — and how they built trust over time.
The duo also offered candid, actionable feedback on pitch decks that were submitted by Extra Crunch Live audience members. (By the way, you can submit your pitch deck to be featured on a future episode using this link right here.)
We’ve included highlights below as well as the full video of our conversation.
We record new episodes of Extra Crunch Live each Wednesday at 12 p.m. PST/3 p.m. EST/8 p.m. GMT. Check out the February schedule here.
Episode breakdown:
- How they met: 1:30
- Building trust: 11:30
- Inside Guideline’s Series B deck: 16:00
- Pitch deck teardown: 33:00
How they met
Senkut and Busque met nearly a decade ago, when Busque was still at TaskRabbit. Several years later, Busque launched out on his own and went fundraising for his original idea. Even though he got a no from Senkut, it wasn’t an easy decision.
Looking back, Senkut said he had much more freedom to follow his instincts while angel investing.
“As an institutional fund with LPs, we were feeling the pressure of checking all the checkmarks,” explained Senkut. “It’s amazing how, sometimes, being more structured or analytical actually does not always lead you to make better decisions.”
When Busque came back around after the pivot, looking to raise a Series B, Senkut called it a “no-brainer,” particularly because of the type of CEO Busque is.
“My opinion of Kevin as a person is that he’s an excellent wartime CEO, but also he’s a product visionary,” said Senkut. “We call them ‘missionary CEOs.’ There are mercenary CEOs who can extract every ounce of dollar from a rock, but we are gravitating much more toward CEOs like Kevin who are focused on product first. People who have a really acute vision of what the problem is, and. a very specific vision for how to solve that problem and ultimately turn it into a long-term scalable and successful company.”
Busque said he was drawn to Senkut based on his level of conviction, explaining that Senkut doesn’t always have to go by the book.
“If he wants to write a check because the founder is great or the product is great, he does it,” said Busque. “It’s not necessarily that he has to see a certain metric or growth pattern.”
Building trust
Obviously, years of staying connected and communicating (and not just about Guideline) laid the foundation for building a relationship. Busque said the honesty in their conversations, including Senkut’s initial rejection, lended itself greatly to the trust they have.
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Lightspeed’s Gaurav Gupta and Grafana’s Raj Dutt discuss pitch decks, pricing and how to nail the narrative
Before he was a partner at Lightspeed Venture Partners, Gaurav Gupta had his eye on Grafana Labs, the company that supports open-source analytics platform Grafana. But Raj Dutt, Grafana’s co-founder and CEO, played hard to get.
This week on Extra Crunch Live, the duo explained how they came together for Grafana’s Series A — and eventually, its Series B. They also walked us through Grafana’s original Series A pitch deck before Gupta shared the aspects that stood out to him and how he communicated those points to the broader partnership at Lightspeed.
Gupta and Dutt also offered feedback on pitch decks submitted by audience members and shared their thoughts about what makes a great founder presentation, pulling back the curtain on how VCs actually consume pitch decks.
We’ve included highlights below as well as the full video of our conversation.
We record new episodes of Extra Crunch Live each Wednesday at 12 p.m. PST/3 p.m. EST/8 p.m. GMT. Check out the February schedule here.
Episode breakdown:
- How they met — 2:20
- Grafana’s early pitch deck — 12:25
- The enterprise ecosystem — 26:00
- The pitch deck teardown — 33:00
How they met
As soon as Gupta joined Lightspeed in June 2019, he began pursuing Dutt and Grafana Labs. He texted, called and emailed, but he got little to no response. Eventually, he made plans to go meet the team in Stockholm but, even then, Dutt wasn’t super responsive.
The pair told the story with smiles on their faces. Dutt said that not only was he disorganized and not entirely sure of his own travel plans to see his co-founder in Stockholm, Grafana wasn’t even raising. Still, Gupta persisted and eventually sent a stern email.
“At one point, I was like ‘Raj, forget it. This isn’t working’,” recalled Gupta. “And suddenly he woke up.” Gupta added that he got mad, which “usually does not work for VCs, by the way, but in this case, it kind of worked.”
When they finally met, they got along. Dutt said they were able to talk shop due to Gupta’s experience inside organizations like Splunk and Elastic. Gupta described the trip as a whirlwind, where time just flew by.
“One of the reasons that I liked Gaurav is that he was a new VC,” explained Dutt. “So to me, he seemed like one of the most non-VC VCs I’d ever met. And that was actually quite attractive.”
To this day, Gupta and Dutt don’t have weekly standing meetings. Instead, they speak several times a week, conversing organically about industry news, Grafana’s products and the company’s overall trajectory.
Grafana’s early pitch deck
Dutt shared Grafana’s pre-Series A pitch deck — which he actually sent to Gupta and Lightspeed before they met — with the Extra Crunch Live audience. But as we know now, it was the conversations that Dutt and Gupta had (eventually) that provided the spark for that deal.
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Greylock’s Asheem Chandna on ‘shifting left’ in cybersecurity and the future of enterprise startups
Last week was a busy week, what with an election in Myanmar and all (well, and the United States, I guess). So perhaps you were glued to your TV or smartphone, and missed out on our conversation with Asheem Chandna, a long-time partner at Greylock who has invested in enterprise and cybersecurity startups for nearly two decades now, backing such notable companies as Palo Alto Networks, AppDynamics and Sumo Logic. We have more Extra Crunch Live shows coming up.
Enterprise software is changing faster this year than it has in a decade. Coronavirus, remote work, collaboration and new cybersecurity threats have combined to force companies to rethink their IT strategies, and that means more opportunities — and challenges — for enterprise founders than ever before. In some cases, we are seeing an acceleration of existing trends, and in others, we are seeing all new trends come to the forefront.
All that is to say that there was so much on the docket to talk about last week. Chandna and I discussed what’s happening in early-stage enterprise startups, whether vertical SaaS is the future of enterprise investing, data and no-code platforms, and then this rise of “shift left” security.
The following interview has been edited and condensed from our original Extra Crunch Live conversation.
What’s happening today in the early-stage startup world?
Chandna has been a long-time backer of startups at their earliest stages, with some of his investments being literally birthed in Greylock’s offices. So I was curious how he saw the landscape today given all that prior experience.
TechCrunch: What sort of companies are exciting for you today? Are there particular markets you’re particularly attuned to?
Asheem Chandna: One is digital transformation. Every company is trying to figure out how to become more digital, and this has been accelerated by COVID-19. Second is information technology today and its journey to the cloud. I would say we might be about 10% or 15% of the way there. Some of the trends are clear, but the journey is actually still relatively early, and so there’s just a ton of opportunity ahead.
The third one is leveraging data for better predictability along with analytics. Every CEO is looking to make better decisions. And you know, most leaders make decisions based on gut instinct and a combination of data. If the data can tell a story, if the data can help you better predict, there’s a lot of potential here.
I view these as three macro trends, and then if one was to add to that, I would say cybersecurity has never been more important than it is today. I’ve been around cyber for over two decades, and just the prominence and importance and priority has never been more important than today. So that’s kind of another key area.
I want to dive into your first category, digital transformation. This is a phrase that I feel like I’ve heard for a decade now, with “Data is the new oil” and all these sorts of buzzwords and marketing phrases. Where are we in that process? Are we at the beginning? Are we at the end? What’s next from a startup perspective?
Due to COVID-19 and because of the way people are working today, digital’s become the primary medium. I would still say we’re early, and you can literally look sector by sector to see how much more work there is to do here.
Take enterprise sales itself, which is early in what I consider digitalization. It’s even more important today than it was a year ago. I’m using video to basically communicate, and then the next piece would basically be trialing of software. Can I allow even complex software to be self trials and can I measure the customer journey through that trial? Then there’s the contracting of the software, and we go to the sale process, can all that be done digitally?
So even when you take something as very mundane as enterprise sales, it’s being transformed. Winning teams, winning software entrepreneurs, they understand this well, and they’d be wise to examine every step of this process, and instrument it and digitize it.
Vertical versus horizontal plays in enterprise
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Join Yext’s Howard Lerman for a Q&A October 13 at 2 pm ET/11 am PT
Heading into the third quarter and earnings season, TechCrunch is excited to announce that Yext CEO Howard Lerman will join us for a live Q&A next Tuesday as part of our continuing Extra Crunch Live series.
The series recently hosted pairs of investors from Accel and Index Ventures and has hosted business leaders, from Mark Cuban to Roelof Botha. Lerman will be one of the few guests who is the CEO of a public company.
But Lerman is no regular public CEO — his company debuted at a TechCrunch event back in 2009, quickly raising capital after the pitch. Yext’s 2017 IPO was therefore an event of interest here at TechCrunch.
What will we talk about? There are a number of things that come to mind, but we’ll certainly get into the impact of COVID-19 on small businesses and how Yext is handling an uneven market. We’ll dig into search, a rising product and revenue area for the company, and how Yext has managed to broaden its product mix without diluting its focus.
We’ll also discuss what changes for a tech CEO heading into the public markets and what advice he might have for companies either considering, or actively going public in 2020. It has been a busy year for startup liquidity, pushing a great number of startups into the public sphere with varying results.
And we’ll riff on where Lerman is seeing the most interesting startups being built, along with your questions. As with all Extra Crunch Live sessions, we’ll snag a few questions from the audience. So make sure your Extra Crunch Live subscription is live and prep your thoughts.
Details follow after the jump. See everyone Tuesday!
Details
Below are links to add the event to your calendar and to save the Zoom link. We’ll share the YouTube link on the day of the discussion:
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Accel VCs Sonali De Rycker and Andrew Braccia say European deal pace is ‘incredibly active’
The other week TechCrunch’s Extra Crunch Live series sat down with Accel VCs Sonali De Rycker and Andrew Braccia to chat about the state of the global startup investing ecosystem. Given their firm’s broad geographic footprint, we wanted to know what was going on in different startup markets, and inside a number of business-model varietals that we are tracking, like API-focused startups and low-code work.
As with all Extra Crunch Live episodes, we’ve included the full video below, along with a number of favorite quotes from the conversation.
Above the paywall, I wanted to share what De Rycker said about the European startup ecosystem: It’s been stuck in my head for the last day, because her comments points to a future where there is no single center of startup gravity.
Instead, considering her bullishness on her local scene, we’re going to see at least three major hubs, namely North America with a locus in the United States, Asia with a possible capital in India, and Europe, with a somewhat distributed layout.
Here’s De Rycker from our chat, responding to my question about how active the European venture and startup scene is today (transcript has been lightly edited for clarity):
What has surprised me even more [than change in the European startup scene over time] is the acceleration in the last couple of years. And I think it’s continued in the last few months, despite the COVID environment.
And that’s really because Europe isn’t just one location, right? It’s a collection of different ecosystems, different locations, different hubs. At any point in time there are 15 to 20 cities that are relevant, and they’ve all sort of reached this tipping point. And together, Europe is at this inflection point, in terms of the quality of entrepreneurs, [and] the number of opportunities. And it feels like it’s all come together with the digitization that’s going on that we’re all, you know, very much believing in right now. And the fact that there’s a ton of capital around. So I would say that we’re seeing a pretty frenetic pace, more than, candidly, pre-COVID, which is not something we expected. […]
But I would say that overall, Europe is incredibly active [regarding] deal pace, deal count, I wouldn’t say it’s very different from what I understand to be the situation in the U.S.
Undergirding what De Rycker said above, TechCrunch recently reported on the financial results of TransferWise, a European fintech unicorn that grew 70% in the last year, to £302.6 million in revenue. Toss in Adyen’s epic run as a public European tech company and there’s lots to celebrate from the continent, even if we don’t read enough about here in the States.
Extra Crunch Live continues with some really damn fun stuff coming up (including a few more that I am hosting). So, make sure you’re in and ready for the next edition as we dig deeper into season two.
Hit the jump for the full chat and some further bits from the transcript.
Sonali De Rycker and Andrew Braccia
Here’s the full video:
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Index Ventures’ Nina Achadjian and Sarah Cannon: ‘There’s basically an infinite bid’ for growth-stage startups
The venture world is swimming in capital these days, and the flood doesn’t appear to be abating.
That’s changing the game for venture capitalists and their firms, which transformed from solo practitioners focused on one stage and a single geographical area to covering all startups in all geos in all industries in just a handful of years.
One firm that has navigated those changes for decades is Index Ventures, one of the first funds to launch in Europe that has evolved into a multi-stage firm in recent years. The firm last raised a total of $2 billion this past April to continue doubling down on all the deals springing up across the world.
This week on Extra Crunch Live, I interviewed Nina Achadjian and Sarah Cannon, two SF-based partners at Index, to discuss what they are seeing in the market, how VC fundraises have changed and continue to change and how they are adapting to the rise of rolling funds and other new seed vehicles. This was the first time that the two came together for a panel, and our conversation was a real blast.
Here’s an edited and condensed version of the conversation, with highlights of the best insights from the panel.
“It’s not easy to just sit on the sidelines and wait till things sort themselves out.”
TechCrunch: September is traditionally a time for fundraises to kick off for the fall, but in this COVID-19 world, everything is different. Who is fundraising right now and what do you see going on?
Nina Achadjian: Well, there are two things. One, there was an incredible pull from the market for technology tools. So many businesses that had put off buying technology or investing in technology really all of a sudden found themselves in a digitally-first world or a digital-only world and therefore, there was a massive pull for technology products. It’s the reason why companies like Shopify and others in the public markets have had just amazing, record quarters.
The second thing is, in venture when we raise these funds, we have a certain time period to deploy them, usually anywhere from two years to five years. So for us as investors, it’s not easy to just sit on the sidelines and wait till things sort themselves out.
So actually, a lot of venture investors have piggybacked off of this incredible pull from the market side and have been investing, I would say, at the same pace, or even a faster pace than we were before.
“There’s basically an infinite bid for these companies.”
Are those paces the same for all stages?
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Extra Crunch Live: Join us today at 2pm EDT/11am PDT to discuss the future of startup investing with Index Ventures VCs Nina Achadjian and Sarah Cannon
The venture capital world is rapidly changing, and thank heavens we have two of the smartest VCs on the future of investing, productivity tools and remote work joining us today to make sense of all the noise.
On Extra Crunch Live today, Sarah Cannon and Nina Achadjian, two VC partners based in Index Ventures’ SF office, will talk about these subjects and more. Plus, we will be taking questions from the audience, so come prepared. Login details are below the fold for EC members, and if you don’t have an Extra Crunch membership, click through to sign up.
As I wrote when we announced the slate last week:
First, we have Nina Achadjian, who officially joined Index Ventures several years ago out of the firm’s SF office and was promoted to partner earlier this year. Achadjian has been searching for and investing into some of the most interesting new collaborative companies that are rebuilding the enterprise from the ground up (which happens to have been a brilliant move given our remote-work world this year). Her investments include such companies as product-management service productboard, sales performance platform Gong, executive assistant marketplace Double and real estate services platform ServiceTitan.
Second, we have Sarah Cannon, who joined Index in 2018 from CapitalG, and who is also based officially out of SF. Cannon made a splash earlier this year with her bullish bet on note-taking and team productivity wunderkind Notion, and has also invested in productivity tools like collaborative presentation software Pitch and smart team messaging app Quill.
Join us today at 2 p.m. EDT/11 a.m. PDT/6 p.m. GMT.
Event Details
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