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A founder’s guide to effectively managing your options pool
There’s an old startup adage that goes: Cash is king. I’m not sure that is true anymore.
In today’s cash rich environment, options are more valuable than cash. Founders have many guides on how to raise money, but not enough has been written about how to protect your startup’s option pool. As a founder, recruiting talent is the most important factor for success. In turn, managing your option pool may be the most effective action you can take to ensure you can recruit and retain talent.
That said, managing your option pool is no easy task. However, with some foresight and planning, it’s possible to take advantage of certain tools at your disposal and avoid common pitfalls.
In this piece, I’ll cover:
- The mechanics of the option pool over multiple funding rounds.
- Common pitfalls that trip up founders along the way.
- What you can do to protect your option pool or to correct course if you made mistakes early on.
A minicase study on option pool mechanics
Let’s run through a quick case study that sets the stage before we dive deeper. In this example, there are three equal co-founders who decide to quit their jobs to become startup founders.
Since they know they need to hire talent, the trio gets going with a 10% option pool at inception. They then cobble together enough money across angel, pre-seed and seed rounds (with 25% cumulative dilution across those rounds) to achieve product-market fit (PMF). With PMF in the bag, they raise a Series A, which results in a further 25% dilution.
The easiest way to ensure you don’t run out of options too quickly is simply to start with a bigger pool.
After hiring a few C-suite executives, they are now running low on options. So at the Series B, the company does a 5% option pool top-up pre-money — in addition to giving up 20% in equity related to the new cash injection. When the Series C and D rounds come by with dilutions of 15% and 10%, the company has hit its stride and has an imminent IPO in the works. Success!
For simplicity, I will assume a few things that don’t normally happen but will make illustrating the math here a bit easier:
- No investor participates in their pro-rata after their initial investment.
- Half the available pool is issued to new hires and/or used for refreshes every round.
Obviously, every situation is unique and your mileage may vary. But this is a close enough proxy to what happens to a lot of startups in practice. Here is what the available option pool will look like over time across rounds:
Image Credits: Allen Miller
Note how quickly the pool thins out — especially early on. In the beginning, 10% sounds like a lot, but it’s hard to make the first few hires when you have nothing to show the world and no cash to pay salaries. In addition, early rounds don’t just dilute your equity as a founder, they dilute everyone’s — including your option pool (both allocated and unallocated). By the time the company raises its Series B, the available pool is already less than 1.5%.
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Playbyte’s new app aims to become the ‘TikTok for games’
A startup called Playbyte wants to become the TikTok for games. The company’s newly launched iOS app offers tools that allow users to make and share simple games on their phone, as well as a vertically scrollable, fullscreen feed where you can play the games created by others. Also like TikTok, the feed becomes more personalized over time to serve up more of the kinds of games you like to play.
While typically, game creation involves some aspect of coding, Playbyte’s games are created using simple building blocks, emoji and even images from your Camera Roll on your iPhone. The idea is to make building games just another form of self-expression, rather than some introductory, educational experience that’s trying to teach users the basics of coding.
At its core, Playbyte’s game creation is powered by its lightweight 2D game engine built on web frameworks, which lets users create games that can be quickly loaded and played even on slow connections and older devices. After you play a game, you can like and comment using buttons on the right-side of the screen, which also greatly resembles the TikTok look-and-feel. Over time, Playbyte’s feed shows you more of the games you enjoyed as the app leverages its understanding of in-game imagery, tags and descriptions, and other engagement analytics to serve up more games it believes you’ll find compelling.
At launch, users have already made a variety of games using Playbyte’s tools — including simulators, tower defense games, combat challenges, obbys, murder mystery games, and more.
According to Playbyte founder and CEO Kyle Russell — previously of Skydio, Andreessen Horowitz, and (disclosure!) TechCrunch — Playbyte is meant to be a social media app, not just a games app.
“We have this model in our minds for what is required to build a new social media platform,” he says.
What Twitter did for text, Instagram did for photos and TikTok did for video was to combine a constraint with a personalized feed, Russell explains. “Typically. [they started] with a focus on making these experiences really brief…So a short, constrained format and dedicated tools that set you up for success to work within that constrained format,” he adds.
Similarly, Playbyte games have their own set of limitations. In addition to their simplistic nature, the games are limited to five scenes. Thanks to this constraint, a format has emerged where people are making games that have an intro screen where you hit “play,” a story intro, a challenging gameplay section, and then a story outro.
In addition to its easy-to-use game building tools, Playbyte also allows game assets to be reused by other game creators. That means if someone who has more expertise makes a game asset using custom logic or which pieced together multiple components, the rest of the user base can benefit from that work.
“Basically, we want to make it really easy for people who aren’t as ambitious to still feel like productive, creative game makers,” says Russell. “The key to that is going to be if you have an idea — like an image of a game in your mind — you should be able to very quickly search for new assets or piece together other ones you’ve previously saved. And then just drop them in and mix-and-match — almost like Legos — and construct something that’s 90% of what you imagined, without any further configuration on your part,” he says.
In time, Playbyte plans to monetize its feed with brand advertising, perhaps by allowing creators to drop sponsored assets into their games, for instance. It also wants to establish some sort of patronage model at a later point. This could involve either subscriptions or even NFTs of the games, but this would be further down the road.
The cutest lil sprite blob I’ve ever seen
#pixelart #gamedev pic.twitter.com/7uBRzs6ix0
— Playbyte (@PlaybyteInc) August 21, 2021
The startup had originally began as a web app in 2019, but at the end of last year, the team scrapped that plan and rewrote everything as a native iOS app with its own game engine. That app launched on the App Store this week, after previously maxing out TestFlight’s cap of 10,000 users.
Currently, it’s finding traction with younger teenagers who are active on TikTok and other collaborative games, like Roblox, Minecraft, or Fortnite.
“These are young people who feel inspired to build their own games but have been intimidated by the need to learn to code or use other advanced tools, or who simply don’t have a computer at home that would let them access those tools,” notes Russell.
Playbyte is backed by $4 million in pre-seed and seed funding from investors including FirstMark (Rick Heitzmann), Ludlow Ventures (Jonathon Triest and Blake Robbins), Dream Machine (former Editor-in-Chief at TechCrunch, Alexia Bonatsos), and angels such as Fred Ehrsam, co-founder of Coinbase; Nate Mitchell, co-founder of Oculus; Ashita Achuthan, previously of Twitter; and others.
The app is a free download on the App Store.
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Barbershop technology startup theCut sharpens its platform with new $4.5M round
TheCut, a technology platform designed to handle back-end operations for barbers, raised $4.5 million in new funding.
Nextgen Venture Partners led the round and was joined by Elevate Ventures, Singh Capital and Leadout Capital. The latest funding gives theCut $5.35 million in total funding since the company was founded in 2016, founder Obi Omile Jr. told TechCrunch.
Omile and Kush Patel created the mobile app that provides information and reviews on barbers for potential customers while also managing appointments, mobile payments and pricing on the back end for barbers.
“Kush and I both had terrible experiences with haircuts, and decided to build an app to help find good barbers,” Omile said. “We found there were great barbers, but no way to discover them. You can do a Google search, but it doesn’t list the individual barber. With theCut, you can discover an individual barber and discover if they are a great fit for you and won’t screw up your hair.”
The app also enables barbers, perhaps for the first time, to have a list of clients and keep notes and photos of hair styles, as well as track visits and spending. By providing payments, barbers can also leverage digital trends to provide additional services and extras to bring in more revenue. On the customer side, there is a search function with barber profile, photos of their work, ratings and reviews, a list of service offerings and pricing.
Omile said there are 400,000 to 600,000 barbers in the U.S., and it is one of the fastest-growth markets. As a result, the new funding will be used to hire additional talent, marketing and to grow the business across the country.
“We’ve gotten to a place where we are hitting our stride and seeing business catapulting, so we are in hiring mode,” he added.
Indeed, the company generated more than $500 million in revenue for barbers since its launch and is adding over 100,000 users each month. In addition, the app averages 1.5 million appointment bookings each month.
Next up, Omile wants to build out some new features like a digital store and the ability to process more physical payments by rolling out a card reader for in-person payments. TheCut will also focus on enabling barbers to have more personal relationships with their customers.
“We are building software to empower people to be the best version of themselves, in this case barbers,” he added. “The relationship with customers is an opportunity for the barber to make specific recommendations on products and create a grooming experience.”
As part of the investment, Leadout founder and managing partner Ali Rosenthal joined the company’s board of directors. She said Omile and Patel are the kind of founders that venture capitalists look for — experts in their markets and data-driven technologists.
“They had done so much with so little by the time we met them,” Rosenthal added. “They are creating a passionate community and set of modern, tech-driven features that are tailored to the needs of their customers.”
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Startups should look to state-of-the-art tech to tackle diseases affecting women
Startups devoted to reproductive and women’s health are on the rise. However, most of them deal with women’s fertility: birth control, ovulation and the inability to conceive. The broader field of women’s health remains neglected.
Historically, most of our understanding of ailments comes from the perspective of men and is overwhelmingly based on studies using male patients. Until the early 1990s, women of childbearing age were kept out of drug trial studies, and the resulting bias has been an ongoing issue in healthcare. Other issues include underrepresentation of women in health studies, trivialization of women’s physical complaints (which is relevant to the misdiagnosis of endometriosis, among other conditions), and gender bias in the funding of research, especially in research grants.
For example, several studies have shown that when we look at National Institutes of Health funding, a disproportionate share of its resources goes to diseases that primarily affect men — at the expense of those that primarily affect women. In 2019, studies of NIH funding based on disease burden (as estimated by the number of years lost due to an illness) showed that male-favored diseases were funded at twice the rate of female-favored diseases.
Let’s take endometriosis as an example. Endometriosis is a disease where endometrial-like tissue (‘‘lesions’’) can be found outside the uterus. Endometriosis is a condition that only occurs in individuals with uteruses and has been less funded and less studied than many other conditions. It can cause chronic pain, fatigue, painful intercourse and infertility. Although the disease may affect one out of 10 women, diagnosis is still very slow, and the disease is confirmed only by surgery.
There is no non-invasive test available. In many cases, a woman is diagnosed only due to her infertility, and the diagnosis can take up to 10 years. Even after diagnosis, the understanding of disease biology and progression is poor, as well as the understanding of the relationships to other lesion diseases, such as adenomyosis. Current treatments include surgical removal of lesions and drugs that suppress ovarian hormone (mainly estrogen) production.
However, there are changes in the works. The NIH created the women’s health research category in 1994 for annual budgeting purposes and, in 2019, it was updated to include research that is relevant to women only. In acknowledging the widespread male bias in both human and animal studies, the NIH mandated in 2016 that grant applicants would be required to recruit male and female participants in their protocols. These changes are slow, and if we look at endometriosis, it received just $7 million in NIH funding in the fiscal year 2018, putting it near the very bottom of NIH’s 285 disease/research areas.
It is interesting to note that critical changes are coming from other sources, and not so much from the funding agencies or the pharmaceutical industry. The push is coming from patients and physicians themselves that meet the diseases regularly. We see pharmaceutical companies (such as Eli Lilly and AbbVie) in the women’s healthcare space following the lead of their patients and slowly expanding their R&D base and doubling efforts to expand beyond reproductive health into other key women’s health areas.
New technological innovations targeting endometriosis are being funded via private sources. In 2020, women’s health finally emerged as one of the most promising areas of investment. These include (not an exhaustive list by any means) diagnostics companies such as NextGen Jane, which raised a $9 million Series A in April 2021 for its “smart tampon,” and DotLab, a non-invasive endometriosis testing startup, which raised $10 million from investors last July. Other notable advances include the research-study app Phendo that tracks endometriosis, and Gynica, a company focused on cannabis-based treatments for gynecological issues.
The complexity of endometriosis is such that any single biotech startup may find it challenging to go it alone. One approach to tackle this is through collaborations. Two companies, Polaris Quantum Biotech and Auransa, have teamed up to tackle the endometriosis challenge and other women’s specific diseases.
Using data, algorithms and quantum computing, this collaboration between two female-led AI companies integrates the understanding of disease biology with chemistry. Moreover, they are not stopping at in silico; rather, this collaboration aims to bring therapeutics to patients.
New partnerships can majorly impact how fast a field like women’s health can advance. Without such concerted efforts, women-centric diseases such as endometriosis, triple-negative breast cancer and ovarian cancer, to name a few, may remain neglected and result in much-needed therapeutics not moving into clinics promptly.
Using state-of-the-art technologies on complex women’s diseases will allow the field to advance much faster and can put drug candidates into clinics in a few short years, especially with the help of patient advocacy groups, research organizations, physicians and out-of-the-box funding approaches such as crowdfunding from the patients themselves.
We believe that going after the women’s health market is a win-win for the patients as well as from the business perspective, as the global market for endometriosis drugs alone is expected to reach $2.2 billion in the next six years.
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Online learning platform CLASS101 bags $26M Series B to support growth
Everything is switching from offline to online mode, spurred by the pandemic, and that also has turned around things for the creative economy. Creative professionals continue to look for ways to monetize their talents and knowledge through online education platforms like CLASS101 that bring stable incomes and improve opportunities.
CLASS101, a Seoul-based online education platform, announced today it has closed $25.8 million (30 billion won) Series B funding to accelerate its growth in South Korea, the U.S. and Japan.
The Series B round was led by Goodwater Capital, with additional participation from previous backers Strong Ventures, KT Investment, Mirae Asset Capital and Klim Ventures.
In 2019, the company raised a $10.3 million (12 billion won) Series A round led by SoftBank Ventures Asia along with Mirae Asset Venture Investment, KT Investment, Strong Ventures and SpringCamp.
Co-founder and CEO of CLASS101 Monde Ko told TechCrunch that the company will use the proceeds to focus on hiring more talent, as well as expanding domestic business and overseas markets in the U.S. and Japan.
Ko and four other co-founders established CLASS101 in 2018, which was pivoted from a tutoring service platform that was founded in 2015, Ko said. It has 350 employees now.
“We will keep supporting creators to monetize their talents and we will also allow creators to expand their revenue streams by selling their goods, digital files and more products via our platform,” Ko said.
When asked about what differentiated it from other peers, CLASS101 provides and ships all the necessary tools and material “Class Kit”, Ko said.
The company offers more than 2,000 classes within a raft of categories, with drawing, crafts, photography, cooking, music and more. It also provides about 230 classes in the U.S. and 220 classes in Japan. There are approximately 100,000 registered creators and 3 million registered users as of August 2021.
CLASS101 launched its platform in the U.S. in 2019 and entered Japan last year. The company opened online classes for kids aged under 14 in 2020.
“CLASS101 is a company that combines the advantages of Patreon and YouTube, offering tailored support for creators while fulfilling users’ learning needs,” co-founder and managing partner at Goodwater Capital Eric Kim said, adding that it is the fastest growing company “in an economic phenomenon in which individuals follow their passions and do what they really enjoy while also making a living from it.”
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Explosion snags $6M on $120M valuation to expand machine learning platform
Explosion, a company that has combined an open source machine learning library with a set of commercial developer tools, announced a $6 million Series A today on a $120 million valuation. The round was led by SignalFire, and the company reported that today’s investment represents 5% of its value.
Oana Olteanu from SignalFire will be joining the board under the terms of the deal, which includes warrants of $12 million in additional investment at the same price.
“Fundamentally, Explosion is a software company and we build developer tools for AI and machine learning and natural language processing. So our goal is to make developers more productive and more focused on their natural language processing, so basically understanding large volumes of text, and training machine learning models to help with that and automate some processes,” company co-founder and CEO Ines Montani told me.
The company started in 2016 when Montani met her co-founder, Matthew Honnibal in Berlin where he was working on the spaCy open source machine learning library. Since then, that open source project has been downloaded over 40 million times.
In 2017, they added Prodigy, a commercial product for generating data for the machine learning model. “Machine learning is code plus data, so to really get the most out of the technologies you almost always want to train your models and build custom systems because what’s really most valuable are problems that are super specific to you and your business and what you’re trying to find out, and so we saw that the area of creating training data, training these machine learning models, was something that people didn’t pay very much attention to at all,” she said.
The next step is a product called Prodigy Teams, which is a big reason the company is taking on this investment. “Prodigy Teams is [a hosted service that] adds user management and collaboration features to Prodigy, and you can run it in the cloud without compromising on what people love most about Prodigy, which is the data privacy, so no data ever needs to get seen by our servers,” she said. They do this by letting the data sit on the customer’s private cluster in a private cloud, and then use Prodigy Team’s management features in the public cloud service.
Today, they have 500 companies using Prodigy including Microsoft and Bayer in addition to the huge community of millions of open source users. They’ve built all this with just six early employees, a number that has grown to 17 recently (they hope to reach 20 by year’s end).
She believes if you’re thinking too much about diversity in your hiring process, you probably have a problem already. “If you go into hiring and you’re thinking like, oh, how can I make sure that the way I’m hiring is diverse, I think that already shows that there’s maybe a problem,” she said.
“If you have a company, and it’s 50 dudes in their 20s, it’s not surprising that you might have problems attracting people who are not white dudes in their 20s. But in our case, our strategy is to hire good people and good people are often very diverse people, and again if you play by the [startup] playbook, you could be limited in a lot of other ways.”
She said that they have never seen themselves as a traditional startup following some conventional playbook. “We didn’t raise any investment money [until now]. We grew the team organically, and we focused on being profitable and independent [before we got outside investment],” she said.
But more than the money, Montani says that they needed to find an investor that would understand and support the open source side of the business, even while they got capital to expand all parts of the company. “Open source is a community of users, customers and employees. They are real people, and [they are not] pawns in [some] startup game, and it’s not a game. It’s real, and these are real people,” she said.
“They deserve more than just my eyeballs and grand promises. […] And so it’s very important that even if we’re selling a small stake in our company for some capital [to build our next] product [that open source remains at] the core of our company and that’s something we don’t want to compromise on,” Montani said.
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YouTravel.Me packs up $1M to match travelers with curated small group adventures
YouTravel.Me is the latest startup to grab some venture capital dollars as the travel industry gets back on its feet amid the global pandemic.
Over the past month, we’ve seen companies like Thatch raise $3 million for its platform aimed at travel creators, travel tech company Hopper bring in $175 million, Wheel the World grab $2 million for its disability-friendly vacation planner, Elude raise $2.1 million to bring spontaneous travel back to a hard-hit industry and Wanderlog bag $1.5 million for its free travel itinerary platform.
Today YouTravel.Me joins them after raising $1 million to continue developing its online platform designed for matching like-minded travelers to small-group adventures organized by travel experts. Starta VC led the round and was joined by Liqvest.com, Mission Gate and a group of individual investors like Bas Godska, general partner at Acrobator Ventures.
Olga Bortnikova, her husband Ivan Bortnikov and Ivan Mikheev founded the company in Europe three years ago. The idea for the company came to Bortnikova and Bortnikov when a trip to China went awry after a tour operator sold them a package where excursions turned out to be trips to souvenir shops. One delayed flight and other mishaps along the way, and the pair went looking for better travel experiences and a way to share them with others. When they couldn’t find what they were looking for, they decided to create it themselves.
“It’s hard for adults to make friends, but when you are on a two-week trip with just 15 people in a group, you form a deep connection, share the same language and experiences,” Bortnikova told TechCrunch. “That’s our secret sauce — we want to make a connection.”
Much like a dating app, the YouTravel.Me’s algorithms connect travelers to trips and getaways based on their interests, values and past experiences. Matched individuals can connect with each via chat or voice, work with a travel expert and complete their reservations. They also have a BeGuide offering for travel experts to do research and create itineraries.
Since 2018, CEO Bortnikova said that YouTravel.Me has become the top travel marketplace in Eastern Europe, amassing over 15,900 tours in 130 countries and attracting over 10,000 travelers and 4,200 travel experts to the platform. It was starting to branch out to international sales in 2020 when the global pandemic hit.
“Sales and tourism crashed down, and we didn’t know what to do,” she said. “We found that we have more than 4,000 travel experts on our site and they feel lonely because the pandemic was a test of the industry. We understood that and built a community and educational product for them on how to build and scale their business.”
After a McKinsey study showed that adventure travel was recovering faster than other sectors of the industry, the founders decided to go after that market, becoming part of 500 Startups at the end of 2020. As a result, YouTravel.Me doubled its revenue while still a bootstrapped company, but wanted to enter the North American market.
The new funding will be deployed into marketing in the U.S., hiring and attracting more travel experts, technology and product development and increasing gross merchandise value to $2.7 million per month by the end of 2021, Bortnikov said. The goal is to grow the number of trips to 20,000 and its travel experts to 6,000 by the beginning of next year.
Godska, also an angel investor, learned about YouTravel.Me from a mutual friend. It happened that it was the same time that he was vacationing in Sri Lanka where he was one of very few tourists. Godska was previously involved in online travel before as part of Orbitz in Europe and in Russia selling tour packages before setting up a venture capital fund.
“I was sitting there in the jungle with a bad internet connection, and it sparked my interest,” he said. “When I spoke with them, I felt the innovation and this bright vibe of how they are doing this. It instantly attracted me to help support them. The whole curated thing is a very interesting move. Independent travelers that want to travel in groups are not touched much by the traditional sector.”
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Pixalate tunes into $18.1M for fraud prevention in television, mobile advertising
Pixalate raised $18.1 million in growth capital for its fraud protection, privacy and compliance analytics platform that monitors connected television and mobile advertising.
Western Technology Investment and Javelin Venture Partners led the latest funding round, which brings Pixalate’s total funding to $22.7 million to date. This includes a $4.6 million Series A round raised back in 2014, Jalal Nasir, founder and CEO of Pixalate, told TechCrunch.
The company, with offices in Palo Alto and London, analyzes over 5 million apps across five app stores and more 2 billion IP addresses across 300 million connected television devices to detect and report fraudulent advertising activity for its customers. In fact, there are over 40 types of invalid traffic, Nasir said.
Nasir grew up going to livestock shows with his grandfather and learned how to spot defects in animals, and he has carried that kind of insight to Pixalate, which can detect the difference between real and fake users of content and if fraudulent ads are being stacked or hidden behind real advertising that zaps smartphone batteries or siphons internet usage and even ad revenue.
Digital advertising is big business. Nasir cited Association of National Advertisers research that estimated $200 billion will be spent globally in digital advertising this year. This is up from $10 billion a year prior to 2010. Meanwhile, estimated ad fraud will cost the industry $35 billion, he added.
“Advertisers are paying a premium to be in front of the right audience, based on consumption data,” Nasir said. “Unfortunately, that data may not be authorized by the user or it is being transmitted without their consent.”
While many of Pixalate’s competitors focus on first-party risks, the company is taking a third-party approach, mainly due to people spending so much time on their devices. Some of the insights the company has found include that 16% of Apple’s apps don’t have privacy policies in place, while that number is 22% in Google’s app store. More crime and more government regulations around privacy mean that advertisers are demanding more answers, he said.
The new funding will go toward adding more privacy and data features to its product, doubling the sales and customer teams and expanding its office in London, while also opening a new office in Singapore.
The company grew 1,200% in revenue since 2014 and is gathering over 2 terabytes of data per month. In addition to the five app stores Pixalate is already monitoring, Nasir intends to add some of the China-based stores like Tencent and Baidu.
Noah Doyle, managing director at Javelin Venture Partners, is also monitoring the digital advertising ecosystem and said with networks growing, every linkage point exposes a place in an app where bad actors can come in, which was inaccessible in the past, and advertisers need a way to protect that.
“Jalal and Amin (Bandeali) have insight from where the fraud could take place and created a unique way to solve this large problem,” Doyle added. “We were impressed by their insight and vision to create an analytical approach to capturing every data point in a series of transactions — more data than other players in the industry — for comprehensive visibility to help advertisers and marketers maintain quality in their advertising.”
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3 tips to align your values with your startup’s culture
You’ve heard the phrase “leading by example,” but what about “leading with values”?
I’ve always led by example by using my values as my guide. Still, it wasn’t until I founded my first company that I fully understood the importance of embedding those values into the company, too.
Integrity, individuals, impact and innovation are the “4 I values” that drive my decisions and the actions of those at my company each day. These are not just words on a wall at our HQ or on a mousepad for our remote crew, but values that everyone in the company lives and breathes. Over the last two years, these four values became even more important and continued to guide me, my family and the leaders at our company.
As organizations map out their “return to the workplace” (NOT “return to work,” because we never stopped working) plans, we should not simply go back to how things were before. Instead, let’s all take a moment to redesign something that sets everyone up for success, with values as the compass. I think you’ll find this approach helps people not only survive, but thrive in the workplace.
Leading with values is, in my experience, the best leadership position to take, and there are three ways to accomplish this goal.
Leave behind old-school mentalities on workplace hierarchy
The tone of the company’s culture comes from the top. The culture you envision for your company will only come about if your employees believe in the practices that you are asking them to implement.
At some point in your career — probably right out of school, a few years in or somewhere in the middle — you experienced a company where treating lower-level employees with less respect is just “a part of the job.” Companies with this type of “paying your dues” mentality tend to work these lower-level employees like grunts until they burn out and leave.
Or they eventually crawl their way up into management-level positions, and the cycle perpetuates itself as they deride the newer crop of employees, eroding any semblance of a healthy culture.
This is not the way.
As a leader, if you want your work environment to indicate inclusivity, support, collaboration and have the essence of a team mentality, you must set the precedent right away. This means stripping away the hierarchy that accompanies work titles and making it clear that your company values contribution based on merit, regardless of position. You are one team, united in your purpose to deliver on your mission, based on your values. This level setting ensures that everyone has skin in the game, and no one has the leeway to treat people poorly.
Don’t get caught in an ivory tower mindset
Early on in my career, I began sharing an office when I could. Those office spaces were purposely not what anyone would consider cool or nice “digs” — not the furniture and certainly not the view. Even as CEO now, I’ve had someone on the team describe my current office as a closet. But it gets the job done.
Simple signals like this send a powerful message, and the signal must remain consistent. Don’t take a limo; rent a cheap car. Don’t fly first class; fly coach. These may seem like minor details, but one of the biggest pitfalls any CEO can encounter is falling victim to an ivory tower mindset — when you become so out of touch with the people you manage, your employees start to notice.
Make a cognizant effort to know your people. Implement a “management by walking around” strategy. Don’t sit in your office all day; get out on the floor among your people. Drop by their desks and ask them how their day is going. Eat lunch in the break room. Put in the effort to attend new hire onboarding.
Not physically back in the office? Drop into Slack channels and Zoom meetings. I once “Zoom bombed” a baby shower for one of our crew members just to hear all the well wishes, and it made my day and theirs. Overall, just be present and humanize your workspace. It pays off in spades.
Be thoughtful and consistent with workplace practices
The tone of the company’s culture comes from the top. The culture you envision for your company will only come about if your employees believe in the practices that you are asking them to implement. More importantly, you will not grow a solid culture if you don’t give these initiatives and practices 100% of your own effort.
For example, one new initiative we rolled out last year is a campaign we call “Free2Focus.” Twice a week, the SailPoint crew is asked to avoid booking meetings for a couple of hours during Free2Focus time. Not only does this address Zoom fatigue, it also gives our crew the chance to catch their breath whichever way suits them best — whether that’s taking a walk, helping with their children’s schooling or just turning off the camera for a bit.
If I want my team to show themselves some grace during the week, I’ve found that I need to apply the same practice. This means not setting up meetings during Free2Focus, not sending emails all hours of the day and night and not judging people for taking breaks when they need them. I trust my team to get the job done largely on their own time and own their own terms. I promise, your employees’ performance will be better because of it.
Being a CEO is more than building on a vision, a product or an idea. It’s about leading your people with values to accomplish mutual goals in a way that doesn’t zap them of their morale or dignity. It’s easy to get caught up in all the things that come with a job, but if you don’t put in the effort to immerse yourself and your values into the entire company, you’ll end up too big for your own good — and certainly too big for your company’s good.
It won’t happen overnight, but remember, the smallest things are often the ones that have the biggest impact. If you’re the leader, lead by example. It’s the only way to build teams that stand the test of time.
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Bright Cellars lands more funding to personalize its subscription-based wine collection
Bright Cellars, a six-year-old subscription-based wine seller has, like many upstarts, evolved over time. While it once sent its club members third-party wines that fit their particular profiles, Milwaukee, Wisconsin-based Bright Cellars says it’s now amassing enough data about its customers that it no longer sells wines made by other brands. Instead, while some of its “original” offerings are admittedly sold by other labels under different names, it is increasingly finding success by directing its winemaker partners to tweak the recipe, so to speak.
“We’re optimizing wine like you might optimize a more digital product,” says co-founder and CEO, Richard Yau, a San Francisco native whose startup entered into a regional accelerator program early on and stayed, though the company is now largely decentralized.
We talked earlier today with Yau about that shift, which investors are supporting with $11.2 million in Series B funding, led by Cleveland Avenue, with participation from earlier backers Revolution Ventures and Northwestern Mutual. (The company has now raised roughly $20 million altogether).
Yau also talked about industry trends that he’s seeing because of all that data collection.
TC: You’re building a portfolio of wines. What does that mean?
RY: We don’t own any land. We’re working primarily with suppliers [as do big companies like Gallo and Constellation], but at a larger scale than before, so we now get to shape what wines taste like and look like, and we can optimize across variables like how sweet should this wine be? How acidic? What do we want its color and brand and label to look like and which segment of our customers will really enjoy this wine the most?
TC: What’s one of your concoctions?
RY: We have a sparkling wine that’s produced in the Champagne method — not a Champagne wine; it’s a domestic wine — using grape varietals that no one uses for sparkling wine, and it’s one of the top-rated wines on our platform. Sparkling wine has been really good for us.
TC: How many subscribers do you have?
RY: We can’t share that, but we saw an acceleration in not just new subscribers throughout the pandemic but also in terms of seeing a larger share of [customers’] wallets going to D2C, and that impacted us pretty positively. Even as things eased up over the summer, we saw that people were cooking and eating at home more [and drinking wine].
TC: What’s the average price of a bottle of wine on the platform?
RY: $20 to $25.
TC: Where are your grape suppliers?
RY: A lot are on the West Coast, in Washington and California, but we also have grape suppliers internationally, including in South America and Europe.
TC: How many wines do you offer, and how long do you trial a wine?
RY: We’ve tested around 600, and at any given time, we’ll have 40 to 50 wines on the platform. We don’t stock everything forever; those that don’t do as well, we basically eliminate.
TC: A lot of D2C brands eventually branch into real-world locations. You aren’t doing that. Why not?
RY: It’s possible that we might at some point, but we like being D2C and it makes a lot of sense in a world where our members now work from home and are home to receive packages. It lines up with e-commerce trends in general. If you’re not buying your groceries at the store anymore, you aren’t buying wines at the store, either.
TC: From where are these bottles shipped?
RY: From a variety of places, but primarily from Santa Rosa [in the Bay Area].
TC: Have you seen the impact the weather is having on California winemakers, some of whom are now spraying sunscreen on their grapes to protect them?
RY: [Climate change] has certainly affected the wine industry. One of the fortunate things about us is we have flexibility in the suppliers we’re working with, so from a business-health perspective, we haven’t been as affected by that. Because a lot of our operations are in California, we did a couple of years ago have some interruptions with distribution where we weren’t able to ship some days; we were also impacted by warm temperatures. But fortunately, so far for this year, we haven’t had any operational or supply-chain disruptions.
TC: Have you been approached by one of legacy firms about a partnership or acquisition?
RY: We’ve had conversations, more in terms of partnerships because we have lots of data and can help them. For example, we can launch a new wine and get feedback almost like a focus group to figure out who likes what. We can split test two different blends for a wine and figure out which does better. That’s where conversations with legacy wine companies have happened.
TC: So they’d pay you for your data.
RY: We’re not opposed to selling data in the future, but we’ve approached it more like, here’s an opportunity to learn about how innovation works at a larger wine company. We don’t expect to be able to do what Constellation does well — with its large salesforce and distributors in every state — but what we can do in a complementary way is understand the consumer.
TC: What have you learned that might surprise outsiders?
RY: Petite sirah [offerings] do as well, if not better than, cabernet and pinot noir on the platform. Cab and pinot are fully 50 times the market size of petite sirah, but we see that our members really like it.
People also like merlot a lot more than they think — pretty much across all demographics. People like to hate merlot, but when we look at red blends that do well . . .
TC: What do people have against merlot?
RY: [Laughs.] Have you ever seen “Sideways?” That has something to do with it, still. Meanwhile, pinot noir remains popular, but people don’t like it as much as [other wine sellers] think.
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