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UpCounsel Connects Businesses With the Best Lawyers For the Job

October 2, 2013

If you Google “lawyer jokes” you’ll be told there are roughly 18.4 million results, of which we’re guessing very few are complimentary. What UpCounsel realized is that it’s not lawyers who should be the butt of those jokes but the process of finding and working with one. Quality and pricing are traditionally very opaque for a business looking to contract for legal services. The result? The likelihood of higher costs and lower quality work. But use UpCounsel to find legal support and you’ve got expert, affordable assistance and not another “did you hear the one about the lawyer…” UpCounsel help independent lawyers manage their practices and connects them with small businesses seeking legal advice. As part of Homebrew’s Bottom Up Economy focus, we love startups that use technology to help small and medium-sized businesses access resources that were previously expensive and largely available only to larger companies. Here’s why we invested in UpCounsel:

Who: UpCounsel CEO Matthew Faustman was a lawyer at a prestigious firm when he realized that the traditional structure was undergoing disruption. No longer would clients pay for overpriced work from associates. And no longer would the smartest young lawyers want to wait around 20 years to make partner, obsessing over billable hours and not delivering the client service or completing the variety of work which drew them to the profession in the first place. So Matt decided to do something about it and teamed up with his friend (and CTO) Mason Blake to offer an alternative. Not Faustman, Blake & Associates, but UpCounsel.

What: UpCounsel helps top independent lawyers run their businesses and identify new small business client opportunities. Matt and Mason saw the end of the brick & mortar firm, foretold by lawyers who were already striking out on their own. At the same, small and medium-sized businesses were struggling to find, research and request bids from top quality lawyers. Instead of calling their accountant, brother-in-law or college buddy for recommendations, why couldn’t they just go to one place online to connect with the best professional for the job?

How: UpCounsel begins with an expanding suite of software services for independent lawyers, including invoicing and billing management. This “virtual backoffice” helps UpCounsel attorneys replace some of the infrastructure they left behind when they struck out on their own. Businesses looking to hire these lawyers visit UpCounsel and submit details of their legal needs. Lawyers respond, usually within 24 hours, and the hiring business can review ratings, costs and expertise to pick the best professional for the job.

To test this approach, UpCounsel bootstrapped to a California launch of its services. After serving more than 1,000 small and medium-sized businesses over the past 14 months, they’ve established a deep understanding of the marketplace’s needs and are beginning national expansion.

Why: Matt left behind the “safe” path to disrupt his own industry. That perked our ears - sometimes the most disruptive forces come from within. However, this disruption wasn’t tinged with contempt or disdain. We saw that UpCounsel believed lawyers could be heroes to their clients if there were simply better ways to connect to and service them. If you’re going to create the world’s largest on-demand legal workforce, you need to understand the legal profession. Matt and Mason combine an entrepreneur’s willingness to take big risks with a personal commitment to the market they service ─ a killer combination.


We’re excited to support many years of UpCounsel growth and to contribute to the decline in those unfair lawyer jokes!

Shyp Makes Shipping Stuff Simple

September 27, 2013

Styrofoam peanuts. Bubble wrap. Searching for the starting point on the roll of packing tape. Losing time from your business to drop off packages or coordinate pickups. How miserable is the shipping experience? Shyp is more like a teleportation device than a mobile app. You just press a button and poof! Whatever you want to send will be picked up, packaged and delivered. Across town or country. Now consumers, makers and small businesses don’t need a third party fulfillment or logistics service. They just need Shyp, which is why we’re proud to lead the financing round announced today. As part of Homebrew’s Bottom Up Economy focus, we love startups that use technology to disrupt long established markets. Shyp is dramatically reducing friction in shipping and logistics. Here’s why we invested in Shyp:

Who: “These guys are just going to find a way to do it.” That’s what we kept feeling after every conversation with the Shyp team. Early on, Kevin Gibbon and Joshua Scott talked about their quiet customer development work in the Bay Area. But soon they were also telling us about bringing on Jack Smith as the Hustler they needed to complete their Hacker and Designer founding team, hiring a great Operations manager and bringing together an incredible syndicate for the financing round, which we’re thrilled to lead. Homebrew looks for a combination of attitude and aptitude in founding teams. Kevin, Joshua and Jack have both in spades.

What: Solving the First Mile shipping problem for consumers and small businesses is an enormous opportunity. Pickup, packaging and delivery to the appropriate carrier (USPS, FedEx, UPS, etc) is unnecessarily painful. Yet, the First Mile has been an underexamined friction in commerce. Countless hours spent waiting in line or on the phone to coordinate shipping; ecommerce items unordered because returning them is cumbersome; overpaying for yet another roll of packaging tape to seal a box. Large corporations can set up shipping departments or contract out to third party logistics services, but consumers and small-medium sized businesses are left holding the bag (or box). That’s where Shyp comes in.

How: Shyp elegantly solves the three major painpoints of small-batch shipping:

  • Pickup - Using the Shyp mobile app, you can easily request pickup at your home, office or any other location.
  • Packing - Your Shyp Hero arrives promptly, transports your item temporarily in a Shyp container and then offsite, professionally packages your item for shipping.
  • Shipping - Based on where your package is going and how fast you want it to arrive, Shyp will select the best option from a number of national carriers, and off your item goes.

There are some other bells and whistles behind the scenes that make Shyp work, but at the end of the day, they’re taking a frustration and turning it into something you no longer have to worry about. Whether you’re mailing a birthday gift, a dozen eBay items or 25 items a day for your Shopify store, Shyp can help.

Why: Sometimes great companies are built from the scars of previous experience. Kevin and Jack were eBay powersellers who knew all about the challenges of running what was effectively a small business from their homes. When this international trio came together (two Canadians and a Brit), they saw the problem had only increased in magnitude over the years. Combining personal history with keen market insights and a “get it done” mentality, we saw mission-driven founders with a long roadmap in their heads.


As Shyp’s Who, What, How and Why unfolded we were increasingly excited about what Kevin, Joshua and Jack can accomplish. We’re looking forward to many years of success and shipping delight.

Plaid Launches the “Modern API for Banking Data”

September 19, 2013

Homebrew has made several investments since the fund’s inception earlier this year and we’re excited that Plaid.io is the first to publicly announce its financing. Software/service as an API is a key component of the Bottom Up Economy, our fund’s focus. Putting data or unbundled functionality in the hands of developers results in new types of services, faster innovation and more affordable applications. We’ve seen this firsthand via Jeff Lawson, CEO and founder of Twilio, who is an active advisor to Homebrew and its companies. Here’s an overview of our investment thesis for Plaid:

Who: Plaid founders Zach Perret and William Hockey kicked off our first meeting with a question: “What is a transaction?” They then proceeded to dissect this seemingly simple inquiry into a number of arcane and nuanced components. Working together at Bain, both founders spent time in the plumbing of financial services systems. Today, those experiences help them navigate the mishmash of financial data upon which they have developed Plaid.

What: Plaid is the first modern API for banking and credit card data, providing developers with a clean, categorized view of user transactions and account balances. Simple, right? Only in the final output. The input is a hodgepodge of siloed data, bank-specific data formats and a host of other legacy structural issues that make data inputs messy.

A world without Plaid leaves merchants, consumers and marketers fumbling around in the dark to access, structure and match financial data from many different sources.

A world with Plaid enables:

  • A B2B lending application that helps identify early spending indicators for when businesses may default on their loans.
  • Accounting software that does a business’s books for them ‘on-the-fly’ as expenses and income are generated.
  • A nonprofit marketing tool that allows donors to track and understand where their donations go.
  • A tax application that scans historical purchases to identify deductible expenses.

How: Plaid works with banks and other transaction data providers to support consumer-authenticated access to spending data. Next they perform *magic* - scrubbing, standardizing, and adding contextual metadata to the transaction. Data can’t be big or valuable if it’s dirty and siloed. Clean data is then made accessible to developers via a simple RESTful API.

Why: The story of Plaid began with the founders brainstorming a new type of local consumer app. At the design stage, they realized that the data they wanted wasn’t readily accessible. So after acquiring and cleaning up the data that is now contained within Plaid they thought that it might also be exceptionally valuable to other companies. They asked other startups. They asked the largest social local apps. They asked financial services companies. Everyone said “Yes, but where do we get that data? We’d absolutely love to use it.” So Zach and William decided to turn Plaid from an app into an API.

At Homebrew we love companies where the Who, What, How and Why all tell a cogent story. We are thrilled to be a part of the Plaid story and look forward to helping William and Zach build the company that they envision.

Hello from Homebrew

July 17, 2013

At Homebrew we believe in the Bottom Up Economy, the idea that as technology keeps getting cheaper, more flexible, more accessible, it can be increasingly leveraged by customers and industries that historically haven’t been able to take advantage of it. And it’s clear this adoption of technology is happening faster and more broadly than ever before.

Our investment philosophy draws us towards products and platforms are supporting the Bottom Up Economy. This includes, for example, new types of commerce, productivity tools, financial services, labor marketplaces and the future of work. The Bottom Up Economy holds great promise for industries old and new. We’ve made investments in companies that are representative of this trend. They operate across a diverse set of markets, including financial technology, AI-driven software, marketplaces, autonomy, agriculture and aerospace. The common thread is the Bottom Up Economy - technology democratizing access to information, products and service, customers and revenue without requiring the specialized skills, substantial resources and significant time needed in the past. These companies also have key characteristics that we look for in our investments: strong network effects, rich data assets, scalable go-to-market strategies and long-term defensibility.


Homebrew’s Focus

Why does Homebrew have a focus on the Bottom Up Economy? It’s a combination of our personal experiences, a conviction about the investment potential of the theme and the nature of Bottom Up founders.


  • Personal Experience: We’ve each spent nearly 25 years working on and investing in these concepts. For Hunter, Second Life, AdSense and YouTube were all about putting tools in the hands of people to help them build audience, community and economic returns from their creativity. And as both an operator and venture capitalist, Satya helped bring products that empowered individuals and small businesses to the mainstream, including AdSense and Twitter. We voted with our feet even before we started voting with Homebrew dollars.
  • Investment Thesis: Growing, profitable companies control their own destinies, and that’s what we hope to help founders build. The transition from a Top Down to Bottom Up Economy will create many innovative companies that will lead their industries for years to come. We also believe that as software eats the world, leaders in every business vertical find themselves facing “buy, build or partner” decisions with innovative upstarts. This dynamic creates fantastic strategic opportunities for founders in countless industries - retail, financial services, transportation, business software, media, etc. - as every leader and company will be paying attention to new companies disrupting their markets.
  • Founder Mentality: We’ve observed that Bottom Up founders are disproportionately mission-driven in their work. Their business models rely on creating real, tangible value for their customers. They believe the problems they solve are empowering people. We believe that being mission-driven is a competitive advantage for an entrepreneur. Mission-driven founders are better recruiters - they can explain the “why” not just the “what” and “how” of their vision. Their convictions make them better leaders, and their employees more loyal, through the ups and downs of startup life. Their passion adds energy to every room and every team and carries them through the ups and downs of building a company. And we just plain like hanging out with them.

Come Talk to Us

If you’re building a startup for the Bottom Up Economy please come chat with us. If you want to work at a Bottom Up Economy, let us know. Want to discuss how the Bottom Up Economy is going to change your existing successful company? Yup, contact us. Interested in debating our thinking - actually, especially if you want to debate - please get a hold of us.


Homebrew is open for business.

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