Robin raises $30M to expand its office reservation software as companies embrace hybrid work

Thanks to the pandemic, teams are more distributed than ever. For some companies, that’s led to a disconnect between lower-level employees and leadership, the latter of whom are generally skeptical of remote work. According to a survey from GoodHire, 75% of managers want workers in the office, citing the potential lack of focus and loss of company culture. But in a separate poll by McKinsey, 87% of workers said that they would embrace the opportunity to work remotely when given the choice.

Micah Remley, the CEO of Robin, argues that businesses can have their cake and eat it too by going the “hybrid” work route — that is, having employees work in-office during a portion of the week and remote for the remainder. Remley joined Robin after Brian Muse and twin brothers Sam and Zach Dunn founded the startup to help companies manage office space using reservation software.

“We want C-suite leaders, facilities, and IT teams to realize that vibrant hybrid workplaces don’t involve complicated technology or elaborate rollout plans,” Remley told TechCrunch in an email interview. “Something that resonates with every leader is that our platform removes barriers from coming into the office and creates a workplace centered on choice. When employees have a choice, returning to the office becomes less about mandates and more about connection.”

Launched in 2014, Robin began as a conference room scheduling app. But over the past 8 years, the platform has expanded to handle various aspects of desk booking, room reservation and guest management. Accessing Robin on the web or mobile, workers can request rooms, desks and equipment before they arrive at an office. Customers who opt for Robin’s guest check-in features can use the platform to have visitors submit any paperwork, like waivers and NDAs, required under the office’s policy.


Image Credits: Robin

Remley pitches Robin as a means of tracking office usage over time as well. On the back end, managers can see how people are using different spaces and tap a calculator to figure out the ideal number of seats, desks and collaborative spaces for a given floor. A newer capability, the “Global Hybrid Trends Dashboard,” shows usage statistics from other companies of the same size, sector and region, providing points of reference.

“Robin combines your favorites, your team, and the people you meet with most to deliver intelligent recommendations on when to come to the office, and takes the pain out of planning by auto-suggesting desks and spaces near your colleagues,” Remley said. “Office utilization analytics gives admins visibility on who is using the office, when they are using it, and which spaces are most commonly used. As companies’ headcount evolves over time, Robin helps customers understand how to optimize their space for the changing times.”

Some workers might not be comfortable with that level of tracking. Robin says that it anonymizes usage data, aggregating it across spaces, floors and buildings. But it’s unclear to what extent the platform does so. We’ve asked Remley for clarification.

Besides competing against office scheduling startups like Envoy, Officely and OfficeRnD, Robin’s major challenge is proving that hybrid work has staying power. According to a TinyPulse study, more than 80% of HR leaders believe hybrid setups to be more exhausting for employees than remote or entirely in-office schedules. Some segments of the workforce are less bullish about hybrid compared to others — Deloitte recently found that over half of women who combine remote and in-office work “have already experienced a lack of flexibility in their working patterns or are concerned this will happen in the future.” But many of the logistical issues around hybrid affect everyone, like balancing staff that comes into the office with the staff that stays at home.

As a piece in Computerworld points out, hybrid work can become a “minefield of unfairness,” rewarding people who are more able and willing to work in the office. In a Gartner poll, 59% of women knowledge workers — who, the poll found, are more likely than men to express a preference for remote work — think in-office employees will be seen as higher performers while 78% believe in-office workers are more likely to be promoted.


Image Credits: Robin

Remley pushes back against the notion that hybrid work is doomed to fail. Software like Robin, he asserts, can give companies the data they need to arrive at a work strategy that pleases most — if not all, admittedly — employees. In any case, the startup hasn’t had trouble lining up customers. Remley says that thousands of teams, including in militaries and governments and at brands like Toyota, Twitter, Mailchimp and Peloton, use Robin to organize their work.

In a vote of investor confidence, Robin today closed a $30 million Series C round led by Tola Capital with participation from Firstmark, Accomplice, Boldstart and Allegion Ventures. Remley says that the capital — which brings Robin’s total raised to more than $59 million — will be put toward platform development, international expansion and growing Robin’s over-190-person headcount.

“Robin has always focused on the hybrid work experience, knowing that eventually, workplaces would shift in that direction. The pandemic accelerated that shift faster than anyone could have predicted,” Remley said. “As companies focus on getting leaner, hybrid work becomes even more attractive as a cost-saving measure. Many of our clients reduced their commercial real estate footprint over the past two years and we expect that to continue. We don’t foresee a broad return to the office in the way we used to think of work … Employees don’t want that, and even in a recession environment, doing a total return to the office doesn’t make economic sense.”

Postscript takes in $65M so Shopify merchants can send more personalized texts to customers

Postscript, an SMS marketing company, raised $65 million in Series C funding and will usher in more ways for brands to personally engage with their customers.

We previously checked in on the company last year when it took in $35 million in Series B funding to continue helping Shopify stores stay in touch with customers via SMS. We also profiled Postscript when it raised $4.5 million in 2019.

In 2021, the company had 61 employees with over 3,500 customers. Today, that has grown to 230 employees and its brand base on Shopify has more than doubled to over 8,500 brands, company CEO Adam Turner told me. It now includes brands like Brooklinen, Homesick, Native, Spikeball and Kopari. In addition, the company more than doubled its revenue.

On average, customers see a 25-time return on their investment using Postscript, Turner said. One of the biggest days the company looks at for traction is Black Friday, but this year, Memorial Day became the company’s largest SMS sending day. He says between 30 and 40 million texts were sent compared to an average of between 5 and 10 million.

He went on to explain that while merchants are worried about a recession, Postscript’s return, essentially $25 for every $1 they put in, enables them to lean into the SMS strategy. For example, merchants who have been using this approach for the past 1 or 2 years are driving 40% of the gross merchandise volume for their stores, he added.

“Merchants are having success, even as Facebook advertising costs increase, and are seeing customer lifetime values stay high,” he added. “They are also more sophisticated and are using SMS as a two-way platform to reply to customers to create a purchase. That creates more value to the end user because it is not just a billboard, but an interaction channel where you can reply and get support for your purchase.”

The company went after new funding after seeing that e-commerce sales via SMS in the United States account for 16% compared to sales via communication systems, like WeChat, where it is 26%, Turner said. “We want to bring the U.S. into the modern times of e-commerce and retail by helping merchants develop relationships and other channels outside their websites,” he added.

Postscript will continue working with Shopify merchants, but the new funding also gives it an opportunity to work with some of its best customers on other platforms. Turner also intends to deploy the funding across sales and marketing, go-to-market and product engineering.

There is still a challenge to provide personalized experiences to customers, but Turner believes that Postscript is creating the best possible approach for using SMS marketing and will continue to build more features with those customers in mind.

Dick Costolo’s venture firm 01 Advisors led the new investment that included participation from Twilio Ventures, Expanding Capital and m]x[v Capital and existing investors at Greylock, Accomplice, Elephant and OpenView. In total, Postscript raised over $100 million in venture-backed funding since the company was founded in 2019.

“In the same way texting changed the way people communicate with each other, Postscript transformed how brands communicate with their customers,” said Costolo in a written statement. “We invest in companies with strong product market fit that are focused on further innovation and scale to bring them into their next phase of growth, and Postscript is the epitome of this profile. They are the future of commerce.”

Fetcher raises $27M to automate aspects of job candidate sourcing

Reflecting the growing investor interest in HR technology startups, Fetcher, the talent acquisition platform formerly known as Scout, today closed a $27 million Series B funding round led by Tola Capital with participation from G20 Ventures, KFund, and Accomplice. The new money — $7 million in debt and $20 million in equity — brings the startup’s total capital raised to $40 million, which co-founder and CEO Andres Blank says is being put toward international expansion and building out the Fetcher platform with new applicant tracking system (ATS) integrations and customer relationship management capabilities.

Fetcher was co-launched in 2014 by Blank, Chris Calmeyn, Javier Castiarena, and Santi Aimetta as a professional networking app called Caliber. After a few years, the founding Fetcher team decided to pivot into recruitment, leveraging some of the automation technology they’d built into Caliber.

“Hiring high-quality, diverse candidates had always been a pain point for me. At one of my prior startups, I personally experienced this issue, and after bringing on a recruiting team to help scale hiring efforts, I saw that their time was also too valuable to be spent on the manual, repetitive tasks that come with sourcing candidates,” Blank told TechCrunch in an email interview. “Rather than relying on expensive staffing fees, I thought there must be a better way to keep sourcing in-house, without it taking up too much time and energy on the talent acquisition teams and hiring managers.”

Through a Chrome extension, Fetcher’s platform ties in with ATS products as well as Gmail and Outlook to allow recruiters to source candidates directly from LinkedIn. Fetcher filters jobseekers into prebuilt email workflows, offering analytics including progress toward diversity goals at the individual, team, position, and company levels.


The Fetcher candidate directory.

Fetcher also performs predictive modeling, automatically gauging the interest of job candidates from their replies, and “automated sourcing,” which runs in the background to push applicants through vetting processes via automated emails.

“A great candidate experience is essential for any company, and part of that experience comes from building long-term relationships with candidates over time. Fetcher’s candidate directory allows companies to remarket to qualified candidates, set up reminders for future connections, and add additional outreach emails to the automated sequences,” Blank said. “Overall, the goal is to make it simple for companies to store, update, and connect with great candidates over time, messaging them about future job opportunities, milestones at the company, and more.”

The reliance on algorithms is a bit concerning, given the potential for bias — Amazon infamously scrapped a recruitment algorithm that favored male engineers and New York City recently placed restrictions on the use of AI in hiring. When asked about it, Blank asserted that the platform’s automation technologies allow for “a more diverse group of prospects” to push through the hiring funnel. He also highlighted Fetcher’s outreach policy, noting that people who don’t wish to be contacted about opportunities via Fetcher can send data deletion requests.

“[O]ur secret sauce here at Fetcher is combining both machine and human intelligence in order to minimize the biases that exist on both sides,” Blank said. “Beyond this, we also have diversity metrics on each search (visible on our platform to the client too), which keeps us in check. If we’re over- or under-indexing anywhere on the gender or demographics front, the platform can course correct. Finally, we remove selection biases from the client. The way we do this is that once a client trusts that the search is heading in the right direction (after vetting a handful of candidates upfront), they place the search on full automation. This means that going forward, they are no longer vetting every candidate, but simply reaching out to all qualified candidates that are found for [a given] open role.”

Blank linked to case studies from customers like, which recently used Fetcher to hire employees mostly from underrepresented groups. But biases can enter at many different, often unpredictable stages of the pipeline. As Harvard Business Review’s Miranda Bogen writes: “For example, if [a] system notices that recruiters happen to interact more frequently with white men, it may well find proxies for those characteristics (like being named Jared or playing high school lacrosse) and replicate that pattern. This sort of adverse impact can happen without explicit instruction, and worse, without anyone realizing.”


Image Credits: Fetcher

The risk doesn’t appear to be dissuading recruiters. Fetcher currently has over 350 customers (growing 10% month-over-month) including Behr Paint, Albertson’s, Foursquare, and Shutterstock., and annual recurring revenue tripled in the last 12 months.

Beyond the strong top-line numbers, Fetcher is benefiting from the broader boom in the HR tech segment, which has seen high venture capital activity over the past few months. According to Pitchbook, HR tech startups collected more than $9.2 billion in venture capital funding globally from January 2021 to October 2021 — a 130% jump from 2020’s total.

“Fetcher is uniquely positioned as one of the only software-as-a-service recruiting platforms to automate both candidate sourcing and email outreach efficiently,” Blank said. “Rather than using a straight database model, Fetcher is the only sourcing solution that can truly automate the sourcing process for companies, based on its unique combination of ‘machine learning with human intelligence.’ This model allows for what feels like a 24/7 sourcer to work in the background for each client. By automating both the sourcing and outreach sides of recruiting, Fetcher can reduce the number of internal sourcers and recruiters a company needs, as well as significantly reduce the budget being spent on outside recruiting firms, agencies, or consultants.”

Fetcher employs 45 people, currently, and plans to double that number by the end of the year.

AngelList Venture takes on rare capital at a $4 billion valuation

After seven years since its last financing round, AngelList Venture has raised new capital, according to sources familiar with the matter. The company announced in a blog post today that it has raised a $100 million Series C led by Tiger and Accomplice at a $4 billion valuation. TechCrunch has reached out for further comment.

AngelList Venture is also opening up a community round, raised on the platform itself, for GPs who have made an investment with them over the past year, the blog post stated.

The fresh capital comes after a massive launch spree from the company, which spent the pandemic beefing up its founder-focused services through rolling funds, roll-up vehicles, AngelList Stack and even a new $25 million fund to back startups solely based on hiring velocity. Plus, it’s adding more capital as it supports more capital. Per data provided by the company, the startup supported 11,300 startup investments last year, up from 3,800 the year prior. It also grew to hold $10 billion in assets, up from $3 billion the year prior.

A question I’ve had for AngelList, for years now, is why not raise venture to meet demand amid growing competition and burgeoning startup formation across the world? It’s the exact question I posed to CEO Avlok Kohli last month when we spoke. He responded with their thesis on hiring.

Kohli said that the company has intentionally kept headcount small so as to limit red tape, and continue to prioritize a high employee to impact ratio.

“We’re growing very, very quickly and our expenses are growing linearly, so we actually have very strong leverage on the financing,” Kohli then said. “That’s the reason why we’ve been in a very different position to be able to continue to grow without needing to take on VC funding.”

He added: “We haven’t had to raise another round of funding, but to be clear, there’s nothing wrong with it: some companies just need capital, sometimes they’re in a race to grow very quickly because it’s a winner take all mentality and the characteristics of that market.”

A counterpoint to his answer is that raising venture isn’t just used for race purposes, it is also used to pursue new opportunities and acquire competitive intelligence. Kohli said he wasn’t compromising, he was just focused on keeping AngelList Venture at a high shipping velocity.

“I think ultimately, companies that raise typically also increase headcount pretty significantly,” he said. “You get slower as you grow, and that’s actually really tough for a technology company, because if your entire focus is on shipping velocity and shipping great product, growing headcount is actually counter to that.”

So, if the capital isn’t for headcount, what is it for? AngelList has told me that they’ve considered taking on some acquisitions in the past, but talks have never gotten to a serious point. It could be for research and development, new funds or, heck, if they want me to stop guessing and just tell me, they should feel free.

Givz raises $3M in seed funding to make donations a marketing tool for businesses

Givz, which has developed an API-powered platform that gives brands a way to convert discounts into donations, has raised $3 million in seed funding.

Eniac and Accomplice co-led the financing for the New York-based startup. Additional investors include Supernode Ventures, Claude Wasserstein of Fine Day, Phoenix Club and Dylan Whitman.

Givz was founded in 2017 to make charitable giving more accessible and convenient for the masses. In March 2020, right before the COVID-19 pandemic hit, the company pivoted from B2C to B2B and used the technology rails it had built to create the e-commerce marketing platform that Givz is today.

The company aims to drive “full-price purchasing behavior” by giving consumers the ability to convert the money they would be saving if getting a discount, and donating it to their favorite charities. 

Prior to the funding, Givz had been working with more than 80 enterprise, mid-market and SMB retail and e-commerce clients such as H&M, Tom Brady’s TB12, Seedlip and Terez, and accumulated more than 40,000 individual users. Since the shift last year, the company has helped drive more than $1 million to 1,100 charities, according to CEO and founder Andrew Forman.

It just launched on Shopify, which Forman says will give the startup access to the 1.7 million retailers that use Shopify as their e-commerce platform.

Givz operates under the premise that “donation-driven marketing” consistently outperforms discounts and costs less, “making it an attractive addition” to corporate marketing.

“We are creating a new marketing category and generating the largest sustainable charitable giving platform in the process,” he told TechCrunch. 

An example of a company using Givz can be found in Tervis, which offered customers “For every $50 you spend, you’ll receive $15 to give to the charity of your choice.” 

“They used Givz technology to allow consumers to choose the charity of their choice and make a turnkey disbursement to hundreds of charities,” Forman explained. “They saw a 20% lift in website conversion and a 17% increase in average order value as a result of this offer.”

Image Credits: Givz

Currently, Givz has eight employees with plans to more than double that number over the next year.

The company plans to use the new capital toward that hiring, and to do some marketing of its own.

“We also want to explore the full potential around the consumer behavior data we collect,” Forman said.

In the short term, Givz is focused on “Shopify growth” with direct to consumer brands.

“But we have successful use cases and huge potential with enterprise retailers and financial institutions,” Forman told TechCrunch. “In the future, we have our sights set on restaurants, the gaming industry and global expansion. I believe that using personalized donations to incentivize consumer behavior has endless application across industries, verticals and continents.”

Eniac partner Vic Singh said that there’s been a trend of brands experimenting with different ways to target the socially conscious consumer. 

“We believe Givz’s donation-driven marketing platform offers brands the best way to attract the socially conscious consumer while elevating their brand, moving more inventory and driving increased order value rather than simplistic traditional discounting,” he added.

Accomplice’s TJ Mahony said that both he and Singh believed SMS would emerge as a new marketing category, which led to early investments in Attentive and Postscript, respectively.

“We both saw a similar opportunity with Givz,” he wrote via e-mail. “Discounting is a well worn marketing muscle, but it’s detrimental to the brand, margins and customer expectations. We believe continuous impact marketing becomes the alternative to discounting and marketers will begin to build teams and budget around thoughtful and persistent giving strategies.”

FreshBooks reaches $1B+ valuation with $130.75M for its SMB-focused accounting platform

FreshBooks, a Toronto-based cloud accounting software company focused on SMBs, announced today it has secured $80.75 million in a Series E round of funding, as well as $50 million in debt financing.

Existing backer Accomplice led the equity financing, which the company described as “an inside round” that propelled FreshBooks to unicorn status with a valuation of “over $1 billion.” 

J.P. Morgan, Gaingels, BMO Technology & Innovation Banking Group and Manulife also participated in the equity investment, along with platform partner and new backer Barclays. With the new capital injection, FreshBooks has now raised a total of more than $200 million in funding over its lifetime.

FreshBooks has built a cloud-based accounting software platform designed to make things like invoicing, expenses, payments, payroll and financial reporting easier for small business owners and self-employed people (and their clients). The company, which says it has served more than 30 million people in over 160 countries, was bootstrapped for the first decade of its life.

As in the case of many startups, FreshBooks was started to solve a pain point for one of its founders. In 2003, FreshBooks’ co-founder Mike McDerment was running a small design agency. When it came to billing clients, he found Word and Excel frustrating to use and felt like they weren’t built to create professional-looking invoices. So he coded his own solution that became the foundation of what is now FreshBooks. The company was self-funded until 2014, when McDerment decided to bring on outside investors and raised $30 million from Oak Investment Partners, Accomplice and Georgian Partners.

In 2019, Don Epperson joined FreshBooks as executive director before transitioning to the role of CEO this year. McDerment, who previously held the position, remains as executive chair of the company.

FreshBooks has 500 employees in Canada, Croatia, Mexico, the Netherlands and the United States — hiring over 100 people in the past year. Also in the last year, the company entered the LatAm market after acquiring Mexico-based e-invoicing company Facturama in September 2020 in an effort to expand its audience in Spanish-speaking markets.

FreshBooks plans to use its new capital toward sales and marketing, research and development and additional strategic acquisitions. 

The company will also use its new funding toward investing in markets that are becoming more regulated and helping owners manage their finances through “simplistic workflows,” according to Epperson.

For example, he said, more business owners are working to become digitally enabled to meet local tax and invoice compliance systems. 

“The need for owners to manage their business digitally has accelerated, and this has changed how small business owners work with bookkeepers and accountants,” Epperson told TechCrunch. “The funding comes as an injection of confidence in our mission to digitally enable small businesses.”

Image Credits: FreshBooks

When it comes to growth metrics like year-over-year revenue percentage growth, the exec was tight-lipped, saying only that FreshBooks has “seen significant growth” in the number of new customers since last year, in part fueled by a pandemic-driven increase in new small businesses.

The pandemic also uncovered the need for us to understand how seismic events affect our customers, Epperson said. 

“After analyzing FreshBooks’ own proprietary data, we learned that businesses owned by women were taking three times longer to recover in the U.S. versus businesses owned by men,” Epperson said. “This stat laid the foundation for conducting more research into how the pandemic was affecting businesses across multiple industries and entering into data-sharing partnerships with local governments to help policymakers enact change in the support available to small business owners.”

Jeff Fagnan, founder and managing partner at Cambridge, Massachusetts-based Accomplice, is clearly bullish on FreshBooks’ potential, saying of his firm’s continued investments in the Canadian company over the past seven years: “With more people choosing self-employment, the FreshBooks team fundamentally believes in the growth of small businesses, and the importance of helping these businesses scale. As insiders, we have better context for how the company is scaling and how the market is growing, and this is why FreshBooks is our largest investment to date.”

FreshBooks is the latest in a growing number of Toronto-based unicorns. Late last month, 1Password raised $100 million in a Series B round of funding that doubled the company’s valuation to $2 billion. 1Password first became a unicorn in 2019.

A conversation with Bison Trails: the AWS-like service inside of Coinbase

Coinbase shares tumbled today to their their lowest point since the company began trading publicly on April 14. The market often moves in mysterious ways, but several drivers could be at play, including Coinbase’s high opening price at the time of its direct listing, its reliance on margins that are all but certain to drop owing to growing competition, and the lack of a lock-up period, meaning more insiders might now be offloading some of their highly valued shares, driving down their price in the process.

Whether Coinbase’s shares fall further still is an open question, but one early investor, Garry Tan, believes what outsiders misunderstand about Coinbase is its potential going forward. Indeed, Tan has said previously that a major revenue driver for the company could ultimately tie to a startup called Bison Trails (also backed by Tan) that Coinbase quietly acquired late last year for an estimated $80 million in stock and that Tan recently likened to an AWS inside of the cryptocurrency exchange.

Curious to learn more, we talked recently with Joe Lallouz, the cofounder and CEO of Bison Trails, which raised $35 million from investors and is now being run as an independent product line by Coinbase. We asked Lallouz — who previously cofounded and sold a company to Etsy — about the opportunity he’s chasing and how his 70-person team fends off what appears to be a growing number of direct competitors. Our conversation has been edited for length below. To listen to our full conversation, including more specifics about Bison’s operations, you can do that here.

TC: Your last company connected hardware makers with buyers. What led you to start a crypto infrastructure business?

JL: First, I often speak in the plural we because I have a co founder [Aaron Henshaw] who I’ve worked with on every company for about 20  years. Prior to Bison Trails, the company that was acquired by Etsy was a pretty large marketplace and I [remained] on the leadership team for a few years, and it was actually there that my interest in crypto and Bitcoin and the blockchain space was really piqued — mostly in the form as an investor. I do have a technical background, I’m an engineer. Aaron is an engineer. And so this idea of programmable money was really interesting to me, and I start doing some angel investing, and suddenly, some of the weirdest and smartest people I’ve ever met were switching careers and focusing on building blockchains or blockchain technology. And [Aaron] and I couldn’t get away from this idea that blockchains and the technology that powers blockchains —  crypto protocols — were going to be super influential in every piece of software that’s built over the next 20 years.

TC: What was the next step?

JL: It was a lot of a whole lot of experimentation. [Aaron and I] built probably each built about three or four different products that weren’t Bison Trails before we built Bison Trails. For one reason or another, they probably weren’t valuable or viable as products but they did give us an incredible amount of insight into what the blockchain ecosystem needed. There was a huge gap in the blockchain market in the infrastructure space. Just really simple things like connecting to a blockchain network, reading from the blockchain network, writing to that blockchain network, doing very blockchain-native things like staking and mining — all that stuff that you may have heard about or read about, it just took a tremendous amount of time.

TC: So you created this company to make it easier for folks to not have to spend time on those things. But you’re not alone. Last week, a company called Alchemy raised money from Coatue and Addition to do something similar. Are you direct rivals?

J: Not exactly. This isn’t a zero sum community. Everyone who’s focused on building blockchain products — whether they’re new blockchains, or infrastructure, or companies around it — is incredibly collaborative.

I do know Alchemy and another company that does similar stuff called Infura and a couple other companies that maybe haven’t raised financing recently so [haven’t been in the news] but are doing really great work in the space to make it easier for people to build. And this isn’t uncommon in a nascent technology space, where companies come in and say, ‘This is a really hard piece of technology to work.’ With blockchains, in particular, we need to make it easier, and different companies are doing that from different angles.

TC: Whose life are you making easier?

JL: We’ve seen a lot of success in supporting the world’s biggest crypto companies. Prior to Coinbase acquiring Bison Trails, we’d announced partnerships with Coinbase to help power their staking nodes proof-of-stake protocols, which is a paradigm shift in the blockchain space. But we’ve also been helping a lot of the other companies that are getting into the space, everyone from that one person who has a smart contract and a dream, all the way to the world’s biggest financial institutions that are building new crypto new products. Whether banks or neobanks, all of them are trying to build on top of these blockchains and a lot of them have been Bison Trail customers for years.

TC: You mentioned the shift to proof of stake from proof of work. Proof of work centers on mining cryptocurrency and proof of stake sounds a little like tenured voting, meaning people are getting rewarded for holding on to currencies longer than others and having a bigger position in them. Is that anywhere near accurate?

JF: It’s almost simpler than that. At its core, the blockchain is a ledger, and a whole lot of people who don’t work together maintain that ledger, which is how mining works. Proof of stake works the same way, but if you hold currency in that blockchain, you vote on what the state of the ledger is. So rather than relying on complex mining algorithms and these large mining operations like Bitcoin does, it relies on people who are incentivized for the state of the blockchain to be right to be correct, because they hold the currency to vote. So really all it is, is a mechanism to incentivize everyday holders of any token to vote on the blocks that are being produced.

TC: And this is is already happening.

JL: So it’s already happening. One of the major blockchains that’s in the middle of this shift is Ethereum 1.0 to Ethereum 2.0. Ethereum has obviously become a very popular blockchain because it was one of the first to enable very intricate, smart contracts, which enables folks to build applications on top of it. And the reason Ethereum has been making the shift is to help it scale. The process of proof of work — mining — can bog down the scalability of a blockchain, meaning how fast it is, how expensive it is, how easy it is to post transactions, and to update the ledger and to maintain the ledger. So this has been a pretty serious trend because it enables blockchains to reach more people and power more intricate applications. It’s a really key piece to blockchain adoption.

TC: And to underscore what Bison Trails is offering to do, what are the features exactly that you’re promising your customers, and do you charge a conventional monthly subscription for these features and services?

JL: We’re a platform not unlike Google Cloud or an AWS where if you’re a builder or someone who wants to participate in a chain, you come to us and instead of needing a team of engineers to spin up nodes and run those and make sure that they’re up and running so that, say, your wallet app is able to connect to a blockchain or that you can take on a new chain or stake on Ethereum; you can instead just click a few buttons in our interface and do that really easily.

The business model is really what we call crypto native SaaS, so folks will pay us in a combination of U.S. dollars, or the crypto equivalent — in some cases like a stablecoin. But also each of the proof-of-stake protocols, as you participate in them, you’re rewarded for participating them, and Bison Trails as a company takes a small cut of that reward.

Again, for more of this conversation, including a look at which nascent crypto startups Lallouz is backing as an investor, you can hear it in its entirety here.

Spearhead launches $100M fourth fund to transform founders into top-notch VC investors

Venture capital continues to get a founder makeover.

Two years ago, I profiled Spearhead, a new program and fund created by Jeff Fagnan at Accomplice and Naval Ravikant, the co-founder of AngelList, to mentor leading founders into becoming the next-generation of angel and seed investors. The premise is and remains simple: offer founders with great networks and hustle $1 million in capital to go out and start writing angel checks and build their own portfolio. Provide a bit of infrastructure and support to guide their decisions, but otherwise, empower founders to learn the craft of investing, and in the process, perhaps even improve their own fundraising prowess.

Well, a lot has changed in the early-stage world, both broadly and with Spearhead over the past nearly three years.

In the last few months (partly driven by AngelList’s push), rolling funds have erupted to completely transform the solo and first-time capitalist world. Rolling funds allow newly-minted VCs to raise smaller amounts of money over time rather than raising a whole fund first, which dramatically lowers the barriers to begin startup investing. How does Spearhead fit into such a world? That’s where the program’s new fund comes into play.

Spearhead announced today that it has raised $100 million for its fourth fund. The basic outline of the program remains the same, but what’s changed is what happens after the formal Spearhead program has finished. “Top-performing founders” will now get $5 million to stake a follow-on rolling fund, as determined by an LP committee. Half the fund is dedicated to follow-on investments, which means that $50 million will be invested in the pro-rata stakes of Spearhead investments. In an interview, Ravikant said “we’re scaling the dollars but we’re reducing the classes” and Fagnan chimed in saying “deeper, fewer bets.”

Applications for the fourth class of Spearhead founders are now open.

Jeff Fagnan and Naval Ravikant of Spearhead. Photo via Spearhead.

Spearhead isn’t built around formal lectures or material, but instead is designed to be an active community that helps train founders for two years and more to learn the art of investing. “We write down the guidelines on how to invest — the stuff that can be taught — on one sheet of paper,” Ravikant said. “And it’s pretty basic stuff … there’s no rocket science here. The work is in the actual day-to-day execution.” The real learning takes place around live deals where it’s all about the discussions between the partners and the other Spearhead participants and alumni.

Spearhead shared some data about where the program stands after about three years. Across three classes, 56 founders have joined the program (with eight unicorns represented), funding 380 startups with $18 million in capital. Among the founders in the program are Alexandr Wang of Scale AI (which was just offered funding at a $3 billion valuation according to The Information), Laura Behrens Wu of Shippo (which raised its Series C earlier this year) and Peter Reinhardt of Segment, which was just bought by Twilio for $3.2 billion.

“We’re an investor, we’re not running a scout program,” Ravikant said. “We are the first and most value-added limited partner in a new GPs career, and just like Y Combinator is sort of pulling these companies into existence, from school kids who otherwise would not have gotten the time of day, we are pulling these funds into existence by helping the founders who until now have been dabbling in angel investing and knew that down the road, they’d have to learn how to be a VC or an angel.”

As Spearhead has matured, the team has learned which founders have succeeded, and what their blind spots are. “The most successful founders in my mind that are Spearhead leads are people who did not consider themselves an angel investor before joining the program,” Fagnan said.

The challenge though has been, ironically for these people, ambition. “The main issue has just been investing too little,” Ravikant said. “They’ve been very timid starting out — as angels they’re used to writing 25 or 50K checks and the idea of writing a 100K or 200K or 500K check is very intimidating.” So, “the mistake so far has been just investing too little, but the quality of that is very very high.”

With Spearhead’s new follow-on financing, the duo hope that they can guide founders toward making bigger bets on riskier projects. They want founders not to have five successes across their five checks, but one mega-success and four failures. “What we’re trying to infuse in them is: we are risk capital and conviction capital [and] we really want them to be taking risks,” Fagnan said.

Unsurprisingly though, Ravikant is a long-term believer. “I personally now invest my own capital into every single Spearhead fund,” he said. “I think it’s basically one of the best deals in venture.”

As funding slows in Boston, its early-stage market could shine

Chris Lynch, a founder and former general partner at Boston-based seed-stage fund Accomplice, remembers “VC Mountain in Waltham.”

Back then, entrepreneurs on funding quests would visit a building overlooking the Waltham Reservoir near Boston where they pitched to a few investors: Matrix Partners, Charles River Ventures and Highland Capital Partners.

“And if they didn’t invest in you, you weren’t getting money to start your company,” Lynch said.

Since then, Lynch has watched the area’s startup ecosystem reach the point where seed-stage firms are ubiquitous, but in a city populated with firms waiting to make first bets, the scene is unsurprisingly undergoing a funding drought. Crunchbase data indicates that the city’s Q2 venture capital pace slowed dramatically, with April seeing far fewer rounds and dollars invested in 2020 than in 2019.

Boston saw just seven known equity funding rounds in April, investments worth a hair under $60 million. In the year-ago April, Boston recorded 24 equity funding rounds worth more than $500 million.

Yet, while the numbers are slow, some Boston tech leaders think seed startups will continue to thrive thanks to accelerators and a healthy base of local early-stage investors. And Lynch, who left Accomplice in 2017, says the venture slowdown might help firms recalibrate their appetite for new deals to a more healthy pace.

“The advantage of more access to capital without a proportional increase in great ideas really waters down the fort,” he said, referring to upmarkets. “A lot of money has been invested in companies before they even proved their ideas were right, and I think even I fell into a trap of competing so hard for deals that I lost sight of a good deal.” He estimates that in our COVID-19 world, investors will start to again take three months for due diligence on a deal, versus three weeks to a signed term sheet.

If Boston’s seed investors becomes more conservative, that means that accelerators — homes of the brightest founders, often before they even have their first customer — will be pressed to react.


Venture Lane, a co-working space and startup incubator for early-stage companies, was nearing its one-year anniversary in the heart of Boston when COVID-19 hit the city.

The incubator, which traditionally hosts 10 startups at a time, made its whole program virtual and reworked existing content to help navigate the climate. Plus, per founder Christian Magel, its tips and workshops were opened up to any early-stage founder, not just the ones enrolled with Venture Lane. Hundreds have signed up, he said.

Edtech notches a win as Teachable is acquired by Hotmart

Edtech has been a hot category for investors for some time. Surging demand for better classes globally from new entrants to the knowledge economy has pushed revenues to new highs. Now, coupled with the rapid propagation of coronavirus forcing dozens of colleges and universities to shut down and move entirely online, the sector is even further in the limelight.

New York-based Teachable rode that wave since its founding in 2013 as Fedora, creating a marketplace for teachers to sell their online courses and build up their own classroom businesses. I covered the startup’s $2 million seed round way back in 2015, and TechCrunch also covered the company’s $4 million series A in 2018.

Now, I get to cover the company’s acquisition by Amsterdam-headquartered Hotmart, a global platform for online courses with deep penetration in the Brazil and global Portuguese and Spanish markets. Sources with knowledge of the transaction said that the acquisition was for around a quarter-of-a-billion dollars, which, if roughly true, would be well above Teachable’s last disclosed valuation of $134 million in 2018.

Teachable has seen prodigious GMV growth on its platform since launch. In total, CEO and founder Ankur Nagpal told me that the platform has driven half a billion in earnings for teachers on its platform, with nearly half of that sum coming in the past year.

That growth has also driven revenues to the bottom line. Unlike some online education marketplaces, Teachable is a SaaS revenue business, and teachers pay a monthly or annual subscription to sell and manage their classrooms (unless they are on the company’s “Basic” plan, in which a 5% revenue fee is also taken). Currently, its “Professional” plan is priced at $99 per month or $948 ($79/month) if billed annually, which includes unlimited students and five admin user accounts.

Nagpal said that the company hit $21 million in revenue in 2019, and is currently on a $25 million run rate, compared to $14 million in the prior year. The company is not profitable, but its losses were “under $2 million” according to him. The company states that over 20,000 students are taught every day across the classrooms on Teachable.

A photo of Teachable’s team. Photo via Teachable.

Explaining the rationale behind selling to Hotmart, Nagpal said that he liked the fact that Hotmart and Teachable have similar missions but very divergent markets, with Teachable focused on the English-language market and Hotmart proving competitive in the Portuguese and Spanish markets. “Synergistically, it just made a ton of sense … we instantly become one of the most valuable online education companies.”

Hotmart is a private company that’s approaching a decade in operation. The company recently received an infusion of cash from Singapore’s GIC and General Atlantic in disclosures last year. Teachable is a smaller company than its new parent, with offices in New York and Durham, North Carolina, but together, the combination of platforms, GMV, and revenues will likely make it a major competitor in the online course space.

Today, that market includes companies like Udemy, which has raised $223 million in venture capital since its founding a decade ago, and Pluralsight, which went public in 2018 on Nasdaq after raising $192 million in VC and is currently valued at approximately $1.40 billion (experiencing the same public market headwinds as every other company these days). Those VC fundraise numbers are from Crunchbase.

Teachable has never raised that level of VC dollars, which makes its exit look much more financially favorable than is typical for edtech companies. Crunchbase has a total of $12.5 million in VC across a couple of rounds, with lead investor Accomplice being one of the presumed major winners in the acquisition, along with Naval Ravikant and Learn Capital. Most of these investors will cash out, except with Accomplice taking a stake in Hotmart to continue its journey with Teachable.

In the other direction, Nagpal himself has also invested as part of Accomplice’s Spearhead fund, in which founders are given small checkbooks to seed invest in promising startups.

Teachable is not changing its branding, mission, or strategy, but hopes to use the leverage from a larger parent company to expand into more international markets and to cross-promote each other’s products. Nagpal will stay on as CEO of Teachable, reporting to the CEO and co-founder of Hotmart, João Pedro Resende.