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Blog and/or Founders Guide: Blog

Welcoming Arash Ferdowsi as our newest Visiting Partner

Posted on by jill

I’m incredibly excited to share that Arash Ferdowsi, Co-founder and former CTO of Dropbox, has joined Pear as our newest Visiting Partner! 

I’ve known Arash since 2007, when Dropbox was still just two people: Arash and his Co-founder Drew. I was immediately inspired by their vision and drive and fortunate enough to be an early backer. The first time I sat down with Arash and Drew, we didn’t talk about the ins and outs of cloud storage, but instead we just talked about becoming good long-term partners.

From left to right: Sequoia’s Mike Moritz, Arash, and myself at a small apartment that was being used as an early Dropbox office. Arash’s co-founder Drew snapped this picture.

Arash helped to grow and scale Dropbox from inception to IPO. As Co-founder and CTO, he truly accomplished so much: building and scaling a company that is used by hundreds of millions of people.

Dropbox IPO in 2018.

Arash departed the company in 2020, and since that time he’s become a successful angel investor. We’ve been fortunate to partner with him on co-investments and welcome him to Pear as a visiting speaker on a number of occasions. 

Arash at Pear’s celebration for Persians in tech

Over the last 15 years, Arash and I have truly built a great relationship on a foundation of true partnership, and I’m very excited to have him join Pear in a more official capacity. 

We’re looking forward to Arash working with Pear founders. Welcome to the family, Arash!

Honey Homes raised $9 million Series A to continue their work building a membership service for busy homeowners

Posted on by jill

Honey Homes, closed their Series A recently, led by Khosla Ventures and supported by Pear and others. To mark the occasion, we thought we’d do a little lookback of our history working with the Honey Homes team over the last few years.

We were first introduced to Honey Homes’ Founder and CEO Vishwas Prabhakara through DoorDash alums, including Evan Moore. The Khosla team knew that the Honey Homes team had a promising early idea and felt Pear would be great seed partners in shaping it into a venture-scalable business. 

Once we met the team, we were excited about backing them for a few key reasons:

  • First of all, we knew this was a massive and unsolved market opportunity. US homeowners spend $250 billion annually on their homes via a highly-fragmented vendor network. The Honey Homes team saw a big opportunity to streamline that network and create a product experience that has never existed for home owners. Most home services companies are marketplaces or managed marketplaces, so it is challenging to make the economics work and keep the quality bar high while scaling. This results in churn from both the supply and demand side. Honey Homes saw an opportunity to do things differently and build out a new model – a homeowner subscription business where they employ handy people. This changes the economics and raises the quality bar substantially.
  • Secondly, they had a clear vision for a product to meet that market demand. The Honey Homes team wanted to build a membership service for busy homeowners to manage and complete to-do lists. I was a new homeowner myself at the time, could easily relate the never ending list of tasks to maintain my home and  the difficulty of finding and keeping handymen. I found the idea of a reliable membership service really enticing. 
  • Finally, we felt that the team was really strong and perfectly suited to tackle this problem. Vishwas was Yelp’s first General Manager and he was also COO of Digit, where he gained valuable experience as an operator. He understood first hand the piecemealing that homeowners have to do for maintenance and improvement work. Avantika Prabhakara, who leads Marketing at Honey Homes, has a rich marketing background from organizations like Opendoor, Trulia, and Zillow, so she’s also deeply familiar with the challenges people face on finding reliable contractors and handyman services.
The Honey Homes app is easy-to-use for homeowners.

Khosla and Pear co-led the seed round in July 2021. Over the last two years, they’ve focused on building out the infrastructure to make this service work, growth in their initial markets, and eliminating key risks in order to raise their Series A. They grew from just a co-founding team to 12 employees and 14 handymen during this time. They also expanded across the Bay Area and Dallas and onboarded 500+ subscription customers. In total, over 20,000 home tasks have been completed for members through more than 10,000 Honey Homes visits over the last two years. 

I’ve been lucky enough to not only be an investor into Honey Homes, but also an early customer. I started using Honey Homes in March 2022, and I’ve had hundreds of tasks completed in my home ranging from fixing a frustrating leaky pond to helping us move our furniture to fixing water-damaged cracks in our ceiling to cleaning out dryer ducts. We use the service so regularly that even my daughter knows our handyman, Miguel, by name. Honey Homes has had an incredibly strong customer response: everyone who hears about it wants to join and they’ve done an excellent job retaining customers. 

We’re so proud of the team for successfully raising their Series A and cannot wait for their continued growth and success!

Welcoming Aparna Sinha as Pear’s newest Partner!

Posted on by jill

We’re excited to share that Aparna Sinha is Pear’s newest Partner! Aparna has made an outsized impact in her time with us as a Visiting Partner, and we couldn’t be more thrilled that she’s joining our team full time.

Aparna brings a strong thesis and a depth of experience in enterprise, developer, and AI to Pear and is excited to work with ambitious founders during this breakout moment in AI. “We’re in the midst of unprecedented technological advancement. AI is re-shaping our present and enabling  the most significant breakthroughs of our lifetimes. The breadth and pace of this technological shift creates an opportunity for startups to disrupt the value chain and reshape how we interact with our world,” says Aparna. “Pear’s co-founder is a female former founder with a PhD in engineering, and our work to grow top female technical entrepreneurs resonates with me,” she continued. 

Over the last six months, Aparna helped launch PearX for AI, a new track of the PearX program tailored towards AI builders. We recently welcomed six teams to the inaugural PearX for AI cohort and are excited for these founders to debut their companies with the world soon. Through the PearX for AI program, Aparna is partnering with founders to define their product, win early customers, and grow. She’s able to leverage her deep experience from Google and in enterprise software to give Pear’s portfolio companies an advantage in the market.

Aparna is also building out our AI advisor community, connecting Pear founders with industry experts from organizations like Stanford, Google, OpenAI, Hugging Face, McKinsey and more. At this moment, AI is touching every single facet of technology and she’s been working to build a top notch council of advisors to assist Pear founders on their entrepreneurial journeys.

We’re so excited to welcome Aparna. If you’re a founder looking to connect, please email her at aparna@pear.vc. 

Welcoming Naomi Chetrit Band as Head of Dorm!

Posted on by jill

Last week, we welcomed Naomi Chetrit Band to the Pear team to lead our Dorm program as a Senior Associate on the investment team. At Pear, we have a long history partnering with students to build the next wave of category-defining companies. We met the founders of companies like Affinity, Viz.ai, Nova Credit, and WindBorne when they were still in school, and we love partnering with students to build businesses from the ground up. With Naomi joining our team, we’re excited to take our program to the next level. 

Pear Garage in 2014. We’ve been investing in students since our start.

Naomi is excited to concentrate on supporting student founders. “My lifelong excitement for learning and education finds its natural home on campuses and inside classrooms. Living in Israel, surrounded by a vibrant startup ecosystem, I developed a strong inclination towards working with founders and supporting early stage startups. Being at Pear now allows me to blend both of my passions, for which I am truly grateful,” says Naomi.

Naomi joins us from the Wharton School, where she just completed her MBA. She also worked as a Pear Fellow during her time at UPenn. Naomi is also an Israeli CPA and Attorney with a career spanning EY-Parthenon, EY, and S. Horowitz & Co.

Naomi pictured with the 2022 Fellowship cohort.

Welcome to the team, Naomi! If you’re a student builder or want to learn more about our Dorm program, you can connect with Naomi on Twitter, LinkedIn, or at naomi@pear.vc. 

Welcoming Louis Corso as Finance Director at Pear

Posted on by jill

Louis’ journey to finance and accounting began with his life-long card playing hobby. He loves working with numbers and rules, and describes himself as quietly a very competitive person. During high school and college, Louis was a professional-caliber Magic: the Gathering player, peaking as a top 300 player in the world while he was in graduate school, but his first love is cribbage, which he grew up playing with his family.

Professionally speaking, Louis is an expert at VC finance. Prior to Pear, Louis worked across finance, tax, and fund accounting at firms like Emergence, Ohana Real Estate Investors, and Foundation Capital. At Pear, Louis’ role involves managing the financial functions of the firm and working across our four funds. He closely monitors budgeting and operating finances, portfolio valuations, LP reporting, and manages the annual tax and audit process. He’s also focused on helping Pear build scalable finance processes that will meet Pear’s needs as we continue to grow.

“I am excited to be at Pear because we are working with founders at the very start of their journey. It’s so fun to be with them from day one, with a ton of excitement and opportunity in front of them. I am also excited to be working with such a humble, collaborative team. It’s fun to feel like we’re all pushing in the same direction, building something together,” Louis says.

Outside of work, Louis lives in the Bay Area with his wife, two young children, and two cats. Questions for Louis? You can reach him at louis@pear.vc or find him on LinkedIn.

PearX S20 alum Federato raised $25 million in Series B funding to accelerate their work running a RiskOps platform for property and casualty insurance

Posted on by jill

Last week, PearX S20 alum Federato announced their $25M Series B round led by Caffeinated Capital and joined by Pear and Emergence Capital. 

We first met Federato’s Co-founders Will Ross and William Steenbergen in March 2020, when they were first year grad students at Stanford’s Graduate School of Business. They were winners of the 2020 Pear Competition and we also invited them to join PearX, our early-stage bootcamp for founders. 

The early Federato team.

When we met Will and William, they only had a product concept and some initial customer validation. But even though they didn’t have solid proof yet, we decided to partner with them in building Federato for a few key reasons:

  • First, we saw a big market opportunity. New risks like climate change, cyber security, and social inflation were changing the landscape. In the insurance industry, risk is the opportunity, and it’s a really hard problem to solve. Insurers operating processes are unable to accommodate emerging risks, but Federato brought a solution to the table to help insurers take on risks of under utilized data assets. We knew at the time that climate change was already affecting the insurance industry in dramatic ways. The elevated frequency of damaging weather events drove more than $100B in uninsured losses between 2018-2019 alone, and this number has only continued to grow since then. 
Elevated frequency of weather events drove more than $100B in uninsured losses in 2018-2019. Read more: SwissRe “Closing the Protection Gap Together”

  • Second, even though they were early in their journey, the founders had a clear vision. We believed in their vision to bring AI into how insurance companies manage the risks associated with an ever-changing world, including the elevated frequency of damaging weather events caused by climate change. They concluded that the best way to achieve this was through a federated learning mechanism (hence the name Federato) that would allow insurance companies to benefit from their own data, as well as other entities’ and insurance companies’ data, safely. We also appreciated that their solution delivered a simple, convenient, and beautiful UX experience, where every interaction was optimized for the user. 
  • Third, we believed in the team from the get go. In their early days, they described themselves as “two deeply passionate, data science/product people who came together to do something about climate change with machine learning.”  Will conceived of the concept behind Federato when he was an Associate at Venrock and William built ML models for the insurance industry at his prior startup, Building Blocks. Together, they researched and deeply understood the space. They didn’t just bring us an idea on a slide deck, but instead they brought a thoroughly thought out plan with multiple in-depth customer interviews, a light proof of concept built on publicly available data, and a clear understanding of the end user and end buyer. We could see that this was a team with a clear analytical mind and a bias for action, which is a rare occurrence.

During PearX, the team coined the term RiskOps, which is about realizing that risk cannot be priced without taking distribution into account. This is a tricky concept to explain clearly, but we worked closely with them to articulate this vision at Demo Day. We also partnered closely with Will and William in developing the first version of their operational underwriting software that continuously monitors risk at every underwriting decision, rather than only a few times per year. Arash and I remember working together to create hand drawn mockups of their initial software over long Zoom meetings during the height of Covid lockdowns. 

Federato’s Co-founder Will presented to thousands of investors during PearX’s first ever virtual Demo Day at the height of the COVID pandemic in 2020.

Shortly after presenting at Pear’s S20 virtual Demo Day, Federato closed a Seed round led by Caffeinated Capital. Between their Seed and Series A rounds, we worked with them on important company-building milestones, like refining the product, building a strong company culture, and navigating long sales cycles through acquiring their first few customers. 

We also helped the Federato team prepare for a successful Series A raise through our Series A Bootcamp. They successfully raised their Series A from Emergence in 2022. 

Federato sharing their vision and progress with Pear’s team and investors in 2022.

In less than a year following the Series A raise, Federato proved itself even more. They truly became an economically efficient marketplace that connects data to the value it can actually create in underwriting. In this year, Federato team tripled their customer base, doubled their spend with existing customers, and entered new segments. 

Riding off of this strong momentum, they just closed their Series B round from Caffeinated, Emergence, and Pear, and we’re excited to continue working with Will, William, and the entire (growing!) Federato team on their mission to modernize the insurance industry!

Generative AI Tech Stack

Posted on by vivien

We recently launched a dedicated AI track to the PearX program and have received a great response. Founders often ask us for guidance on how to build a moat for their AI startup. There are many aspects to this question but to kick things off, we are sharing a presentation I gave at SF Tech Week that covers background on the emergence of Generative AI, the highest priority areas of application particularly in enterprises, and what we believe enables a ‘moat’ for AI startups.

Generative AI Tech Stack Presentation at SF Tech Week

Generative AI is a game changing technology for humanity. A quote from one of my heroes, Professor Fei Fei Li at Stanford, and also was head of AI at Google Cloud for a while captures the excitement well:

“Endowing machines with generative capabilities, has been a dream for many generations of AI scientists” 

Seminal technologies which have led to the recent Generative AI breakthroughs include Cloud computing and within that advancements in GPUs, Kubernetes and open source frameworks like PyTorch provide an efficient and widely accessible substrate for model training and inference.

Research breakthroughs on the transformer neural network, its use on internet scale datasets and recent advancements in AI alignment are at the heart of most of the Generative AI capabilities today.

By no means are we at a peak yet, as research continues to improve efficiency at the hardware, software and services layers. Most interestingly to increase context lengths and optimize AI application architectures for accuracy, latency, and reliability. We cover some of these topics in depth in our Perspectives on AI fireside series.

It is clear that Generative AI techniques apply to multiple modalities. There has been a steady stream of models, both open source and proprietary in the major areas of NLP, Image, Video, Voice and also physical synthesis of Proteins.

Applications to both consumer and enterprise software abound and are already starting to change the shape of what software can do. We highlight some of the opportunities to build vertical and horizontal applications as well as tooling and infrastructure.

Of course there is hype when it comes to Generative AI, and in some sense it is almost too easy to create new functionality by building a thin layer over a foundation model that somebody else has built. While there are some businesses to be built in that way, for a venture scale business, we posit that a deeper moat is required to build. A large business that benefits rather than crumbles from rapid evolution of technology at the lower layers of the AI stack requires several moats.

Our thesis is that Applications will be composed of ensembles of specialized models, not just foundation models, but specialized models that are customized via fine tuning or in-context learning or a range of other techniques to complete part of a use case or workflow. These specialized models should utilize proprietary data specific to a domain and help to personalize the output of the application as well as ensure accuracy. A by product may also be lower cost to serve. Overall such an architecture will be a way to build lasting value and be more immune to disruption.

Tooling and infrastructure supporting the development of new applications of this kind is second part of our investment thesis. In particular, data and tooling companies to evaluate and ensure safety, accuracy, and privacy of these applications will be in demand. Lastly a few new infrastructure companies and capabilities will advance the development of these applications. We see emerging companies at every layer of the AI stack (slide 9). With that thesis in mind,  building a moat is fundamentally not that different in AI than in any other emerging space (slide 10).

Enterprise readiness for adoption of AI is arguably higher than it has ever been with the widespread acceptance of cloud computing, API integrations, and existing investments in data analytics teams and software. The hurdles to enterprise adoption are also not new, these are the same requirements that any cloud service has to meet, with perhaps a stronger need for ease of use and simplicity given the lack of existing AI/ML talent.

We conclude by quoting what many others have already said, that this is a great time to start a company!

PearX alums WindBorne closed a $6 million round to improve forecasts and mitigate the climate crisis with smart weather balloons

Posted on by jill

Last week, PearX S19 alum WindBorne Systems announced their $6M seed round led by Footwork Ventures and joined by Pear, Khosla Ventures, and others. We love WindBorne’s founding story as it embodies everything we believe at Pear about mission-driven, high perseverance founders. 

I was lucky to meet the founders of WindBorne back in the spring of 2019, when they were undergraduate students at Stanford University. They showed up to my office hours with a balloon in tow, similar to the one pictured below. 

Early prototype of a WindBorne balloon

I had no idea that the homemade-looking device was a low cost, highly durable weather balloon that could fly at a wide range of altitudes. They called this balloon ValBal for (Vent to sink, Ballast to rise).

We decided to partner with WindBorne for two reasons:

  • First, we believed in the founding team. They had demonstrated a clear mission, a strong passion, and an incredible ability to execute. They’d been addicted to this idea since they were freshman at Stanford as members of the Stanford Student Space Initiative. Constrained by a student budget, they used ingenuity and engineering to build weather balloons that would fly for a few hours and then pop. Over the years, they kept adding sensors and extending flight time, steadily improving their product. By the time I met them, they had already completed 26 test flights and broken four world records. 
Map of flight tests the WindBorne team conducted while in college
  • Second, they were capturing data that no one else was capturing. At the time, we were not 100% sure of the value of such data, but after making a few calls, we discovered potential customers were interested in learning more about what the balloons could do. 
WindBorne team testing balloons during their time at Stanford

With that, we invited WindBorne to join PearX’s Summer 2019 cohort, where we partnered closely with the founders to understand the most attractive market opportunity to go after. Through customer interviews, they discovered a massive data gap: only about 15% of the Earth’s surface has regular in-atmosphere observations, but weather is a global system. To better predict the weather, you need better weather data. Existing technologies couldn’t plug that gap, because the laws of physics prevent satellites from collecting the most critical weather observations. That’s where balloons come in: they’re able to collect data where satellites can’t.

Kai during PearX Summer 2019

Investors were convinced of the potential, and following S19 Demo Day, Windborne closed a successful seed round led by Khosla and Ubiquity Ventures. They spent the last four years growing the company: from iterating on their go-to-market strategy to team building to customer interviews to strategy sessions and more. We had the privilege to work side-by-side with John, Kai, Joan, Andre, and the entire WindBorne team every step of the way.

WindBorne team at PearX 2019 Demo Day

Last fall, the WindBorne team went out to begin raising their next round, in the midst of a tough economic climate. As PearX alums, we invited them to participate in our PearX S22 Demo Day, where Kai shared the latest happenings with thousands of investors in the Pear network. We’re so proud of the entire team for this next step in their journey.

PearX S22 Demo Day Presentation

I recently visited the new WindBorne HQ in Palo Alto, just a few weeks after the team moved in, and I left with a smile on my face. The offices were scrappy, the team was as determined as ever, and they were telling me all about the new advances with their product. I couldn’t help but look back and remember the first time they ever walked into my office as Stanford students and feel proud of how far they’ve come. I know this is just the beginning for WindBorne. We are so excited to continue to partner with them and to welcome Footwork and others to the team. 

Recapping 2023 SF and LA Tech Weeks

Posted on by jill

San Francisco and Los Angeles Tech Weeks are now complete, and we were excited to be a part of the celebration again this year! We hosted four events this year. Thank you to the founders and entrepreneurs who joined us at our events. Here’s a quick recap of our Tech Week events:

Hiring your first engineer

To kick us off, Pear’s Talent Partner Matt led a presentation and discussion on hiring your first engineer. Matt shared the strategy and process behind what hiring looks like for a first time founder – sharing advice and insight on timing, what to look for, and how to attract, find, assess and close your first hire. 

Enterprise opportunities in generative AI 

We pushed the capacity limits in our quaint SF office with nearly 100 guests for our Generative AI talk, led by Aparna. She presented on the latest trends, technologies, and applications in generative AI, specifically as it pertains to early founders. 

The Gusto founding story

For our final SF Tech Week event, Pear’s Founding Managing Partner, Pejman, sat down with Gusto’s CEO and Co-founder, Josh Reeves. They discussed the journey building Gusto from the ground up into a platform for 300,000+ businesses that is worth $10B today. Josh’s biggest piece of advice is to always focus on the customer first and foremost. 

What Apple Reality Pro means for XR

Last week we moved south for LA Tech Week, where Pear’s Partner Keith held a discussion in sunny Santa Monica exploring Apple Reality Pro and the ripple effects it will have on XR. It was great to meet so many XR founders, builders, and enthusiasts of the space!

Thanks to all who joined us for SF and LA Tech Weeks. We are so grateful to our community near and far! 

Looking to connect with someone from the Pear team? Head over to our team page and feel free to reach out, we’d love to hear from you. If you’d like to join us at a future event, keep an eye on our events page. 

Dorm room to board room: key learnings from Pear VC’s masterclass in pre-seed investing with Stanford founders

Posted on by jill

Last month, I had the immense privilege of helping judge Pear VC’s Stanford student Competition. The event highlighted the brightest student founders from Stanford vying for their first check. The Pear Competition has a history of identifying and nurturing exceptional talent, supporting unicorn companies such as Viz.ai and other breakout companies including Nova Credit, Federato, Conduit Tech, and Wagr.

Pre-seed is a notoriously hard stage to invest, as startups often lack any metrics, product, traction, or proven revenue model. The excitement and challenge lies in the ability to identify hidden gems despite the uncertainty, requiring a skillset that combines intuition, experience, and a deep understanding of market landscapes across a wide range of industries.

With the invaluable experience of judging and doing diligence on close to 100 founders alongside renowned investors and proven operators, Mar Hershenson and Ilian Georgiev, I wanted to share 5 key takeaways in pre-seed investing from one of the best early-stage VCs:

1. Passion and Market Insight

Impressive founders had a deep understanding of their market, derived from a unique blend of professional experience, customer interviews, and thorough research. They could clearly pinpoint “hair on fire” problems and delve into pain points along the customer journey in excruciating detail, ultimately laying the foundation for a compelling vision for the problem they aim to solve.

These founders masterfully answered highly nuanced follow-up questions, while still demonstrating a humbling awareness of what they still needed to learn.

2. High Learning Rate

Another exciting key trait of founders was a demonstrated “high rate of learning”. These founders were unafraid to openly discuss assumptions and hypotheses that were proven wrong, providing insights into how their understanding of the market and potential solutions continually evolved. This grounded reflection illustrated their willingness to pivot when necessary, ensuring they could navigate the inevitable uncertainties of the startup journey.

3. Execution Velocity

Several founders stood out with their relentless drive to move fast. They leveraged no-code tools, pounded the pavement to connect with customers, and used smokescreen tests to gauge demand. These tenacious entrepreneurs consistently found ingenious, low-cost, and scrappy ways to rapidly test hypotheses, never allowing a single obstacle to halt their progress. They made do with what they had, not waiting on “ideal” resources or the “perfect team”.

4. Commitment

High commitment and perseverance was another trait we looked for in founders. Despite the glamour of eye-catching TechCrunch headlines, the reality is that the founder journey is an uphill marathon. Most startups must navigate the treacherous “pit of despair” for an average of 18 months before achieving product-market fit. A demonstrated ability to weather these upcoming challenging times after the initial excitement fades is a vital asset to tackle the inevitable hurdles of entrepreneurship. 

Some of these founders had a history of starting previous businesses, often grappling with numerous setbacks and pivots. They could detail stories of struggles and challenges they faced in their founding journey, demonstrating a balance of grit and determination to continually refine their craft. 

5. True Meaning of a “No”

Perhaps the most insightful lesson was that a “no” from a VC often does not mean that the founder or the business wasn’t exceptional. Many factors can contribute to a “no” despite an impressive company, such as a competing investment, the market size, or a mismatch with the VC’s sector focus. Founders often forget that building an outstanding business and securing funding from a specific VC are distinct pursuits. Never let a single “no” derail your founding journey. Embrace the challenge, learn from the feedback, and keep building. Success is not solely defined by the checks you secure but by the impact you create through the relentless pursuit of your vision.

In essence, the art of pre-seed investing lies in recognizing founders who possess a unique combination of passion, adaptability, and resilience. These entrepreneurs are driven by their vision and demonstrate an uncanny ability to navigate uncertainty, making them invaluable assets in the early-stage startup ecosystem, and proving that success is ultimately measured by the tenacity to transform a compelling idea into a lasting impact.

Guest post written by Alex Wu, a Pear Fellow at Stanford.