Personal blog of Yzmir Ramirez

Trust wants to give smaller businesses the same advantages that large enterprises have when marketing on digital and social media platforms. It came out of beta with $9 million in seed funding from Lerer Hippeau, Lightspeed Venture Partners, Upfront Ventures and Upper90.

The Los Angeles-based company was started in 2019 by a group of five Snap alums working in various roles within Snap’s revenue product strategy business. They were building tools for businesses to fund success with digital marketing, but kept hearing from customers about the advantage big advertisers had over smaller ones — the ability to receive good payment terms, credit lines, as well as data and advice.

Aiming to flip the script on that, the group created Trust, which is a card and business community to help digital businesses navigate the ever-changing pricing models to market online, receive the same incentives larger advertisers get and make the best decision of where their marketing dollars will reach the furthest.

Trust dashboard

Trust does this in a few ways: Its card, built in partnership with Stripe, enables businesses to increase their buying power by up to 20 times and have 45 days to make payments on their marketing investments, CEO James Borow told TechCrunch. Then as part of its community, companies share knowledge of marketing buys and data insights typically reserved for larger advertisers. Users even receive news via their dashboard around their specific marketing strategy, he added.

“The ad platforms are walled gardens, and most people don’t know what is going on inside, so our customers work together to see what is going on,” Borow said.

The growth of e-commerce is pushing more digital marketing investments, providing opportunity for Trust to be a huge business, Borow said. E-commerce sales in the U.S. grew by 39% in the first quarter, while digital advertising spend is forecasted to increase 25% this year to $191 billion. Meanwhile, Google, Facebook, Snapchat and Twitter all recently reported rapid growth in their year-over-year advertising revenues, Borow said.

The new funding will go toward increasing the company’s headcount.

“We have active customers on the platform, so we wanted to ramp up hiring as soon as we went into general release,” he added. “We are leaving beta with 25 businesses and a few hundred on our waitlist.”

That list will soon grow. In addition to the funding round, Trust announced a strategic partnership with social shopping e-commerce platform Verishop. The company’s 3,500 merchants will receive priority access to the Trust card and community, Borow said.

Andrea Hippeau, partner at Lerer Hippeau, said she knew Borow from being an investor in his previous advertising company Shift, which was acquired by Brand Networks in 2015.

When Borow contacted Lerer about Trust, Hippeau said this was the kind of offering that would be applicable to the firm’s portfolio, which has many direct-to-consumer brands, and knew marketing was a huge pain point for them.

“Digital marketing is important to all brands, but it is also a black box that you put marketing dollars into, but don’t know what you get,” she said. “We hear this across our portfolio — they spend a lot of money on ad platforms, yet are treated like mom-and-pop companies in terms of credit. When in reality Casper is outspending other companies by five times. Trust understands how important marketing dollars are and gives them terms that are financially better.”

Small and medium enterprises have become a big opportunity in the world of B2B technology in the last several years, and today a startup that’s building tools aimed at helping them manage their teams of workers is announcing some funding that underscores the state of that market.

Homebase, which provides a platform that helps SMBs manage various services related to their hourly workforces, has closed $71 million in funding, a Series C that values the company between $500 million and $600 million, according to sources close to the startup.

The round has a number of big names in it that are as much a sign of how large VCs are valuing the SMB market right now as it is of the strategic interest of the individuals who are participating. GGV Capital is leading the round, with past backers Bain Capital Ventures, Baseline Ventures, Bedrock, Cowboy Ventures and Khosla Ventures also participating. Individuals include Focus Brands President Kat Cole; Jocelyn Mangan, a board member at Papa John’s and Chownow and former COO of Snag; former CFO of payroll and benefits company Gusto, Mike Dinsdale; Guild Education founder Rachel Carlson; star athletes Jrue and Lauren Holiday; and alright alright alright actor and famous everyman and future political candidate Matthew McConaughey.

Homebase has raised $108 million to date.

The funding is coming on the heels of strong growth for Homebase (which is not to be confused with the U.K./Irish home improvement chain of the same name, nor the YC-backed Vietnamese proptech startup).

The company now has some 100,000 small businesses, with 1 million employees in total, on its platform. Businesses use Homebase to manage all manner of activities related to workers that are paid hourly, including (most recently) payroll, as well as shift scheduling, timeclocks and timesheets, hiring and onboarding, communication and HR compliance.

John Waldmann, Homebase’s founder and CEO, said the funding will go toward both continuing to bring on more customers as well as expanding the list of services offered to them, which could include more features geared to frontline and service workers, as well as features for small businesses who might also have some “desk” workers who might still work hourly.

The common thread, Waldmann said, is not the exact nature of those jobs, but the fact that all of them, partly because of that hourly aspect, have been largely underserved by tech up to now.

“From the beginning, our mission was to help local businesses and their teams,” he said. Part of his inspiration came from people he knew: a childhood friend who owned an independent, expanding restaurant chain, and was going through the challenges of managing his teams there, carrying out most of his work on paper; and his sister, who worked in hospitality, which didn’t look all that different from his restaurant friend’s challenges. She had to call in to see when she was working, writing her hours in a notebook to make sure she got paid accurately. 

“There are a lot of tech companies focused on making work easier for folks that sit at computers or desks, but are building tools for these others,” Waldmann said. “In the world of work, the experience just looks different with technology.”

Homebase currently is focused on the North American market — there are some 5 million small businesses in the U.S. alone, and so there is a lot of opportunity there. The huge pressure that many have experienced in the last 16 months of COVID-19 living, leading some to shut down altogether, has also focused them on how to manage and carry out work much more efficiently and in a more organized way, ensuring you know where your staff is and that your staff knows what it should be doing at all times.

What will be interesting is to see what kinds of services Homebase adds to its platform over time: In a way, it’s a sign of how hourly wage workers are becoming a more sophisticated and salient aspect of the workforce, with their own unique demands. Payroll, which is now live in 27 states, also comes with pay advances, opening the door to other kinds of financial services for Homebase, for example.

“Small businesses are the lifeblood of the American economy, with more than 60% of Americans employed by one of our 30 million small businesses. In a post-pandemic world, technology has never been more important to businesses of all sizes, including SMBs,” Jeff Richards, managing partner at GGV Capital and new Homebase board member, said in a statement. “The team at Homebase has worked tirelessly for years to bring technology to SMBs in a way that helps drive increased profitability, better hiring and growth. We’re thrilled to see Homebase playing such an important role in America’s small business recovery and thrilled to be part of the mission going forward.”

It’s interesting to see McConaughey involved in this round, given that he’s most recently made a turn toward politics, with plans to run for governor of Texas in 2022.

“Hardworking people who work in and run restaurants and local businesses are important to all of us,” he said in a statement. “They play an important role in giving our cities a sense of livelihood, identity and community. This is why I’ve invested in Homebase. Homebase brings small business operations into the modern age and helps folks across the country not only continue to work harder, but work smarter.”

There are two sides to starting a new business. On one side, entrepreneurs need creativity, imagination — a dream, essentially — to find, build, and market a new product to users and consumers. But on the other side, they have to deal with the regulatory state and all the minutia that comes with running any business in the 21st century.

That includes such delightful topics as choosing a particular model for incorporation, ensuring that a business has the right licenses to operate, and tracking all the legal changes happening in 50 state legislatures every year. It can be inordinately complicated (and expensive!) to ensure that your business is ready and legal.

That’s where ZenBusiness comes in. The Austin-based startup wants to empower entrepreneurs to build businesses large and small by dramatically simplifying the processes required to launch a business and then grow it.

When I last chatted with the company 18 months ago, they had just raised a $4.5 million seed round and had launched its platform. Today, it’s announcing that it has raised a new $15 million series A round led by return backer Greycroft, along with returning investors Lerer Hippeau and Revolution’s Rise of the Rest fund, alongside new investors Rosecliff Venture Partners, Interlock Partners and Recruit Strategic Partners.

The company launched with a product that was essentially an automated registered agent for new entrepreneurs. Under state incorporation laws, companies must designate a so-called “registered agent” to receive official notices from regulatory agencies, and so ZenBusiness chose this strategic point for entry into the market.

When I last chatted with CEO Russ Buhrdorf, he described rolling up this market as one of the key initial targets for the company:

ZenBusiness is the brainchild of Ross Buhrdorf, who joined vacation rental marketplace HomeAway five months after its inception as founding CTO, and stayed for a decade until its acquisition by Expedia in 2015 for $3.9 billion. Buhrdorf intended to take a year off, but “didn’t quite make it a year” he told me.

He explained to me that HomeAway in many ways followed a rollup playbook, “raising $400 million and acquired 26 companies.” Bringing that rollup lens while exploring new spaces, he ran into the corporate legal services market, which offers help to companies to keep them in compliance with the law. Buhrdorf liked what he saw. “It’s different in all 50 states, highly-regulated, which is great for technology, it is overpriced, and they underserve their customers.” He says the space is “completely ripe for disruption.”

Since that time, the company has expanded its product to help entrepreneurs get beyond merely incorporating to actually building out their business by recommending services like banking, lending, tax preparation, website building, and more. The hope is to provide a “worry-free” guarantee to entrepreneurs so that they can get those early critical logistics out of the way and back to actually operating and growing their business.

“Small businesses come through this funnel, they don’t necessarily know exactly what to do. So we curate that solution, and then we provide them with the basics for them to get up and running and to be successful,” Buhrdorf said.

He explained that the company has built out some tools itself such as a simple webpage creator, but in the long run, he hopes to partner with other providers who integrate into the ZenBusiness platform. For instance, ZenBusiness has partnered with Xero as the company’s main accounting provider, while also backstopping that offering with accountants working at ZenBusiness. The idea is that the automated tooling plus a little human touch can help most owners handle the day-to-day challenges of running a business.

The ZenBusiness team in 2018. Photo via ZenBusiness.

Buhrdorf is particularly focused on keeping the product very self-service and automated to allow it to focus on these smaller customers. “Many of the companies that you cover that are in the enterprise space, who provide solutions for medium-sized businesses, they have to charge, they have to have sales forces, it’s very competitive there,” Buhrdorf said. “What we’re after is the segment that’s underserved, it’s the long tail of the small business segment.”

ZenBusiness has expanded its services, and it is hoping to use the fresh infusion of capital to invest in building out community features that will allow small business owners to swap tips with each other and help one another grow their businesses (presumably with some guidance from ZenBusiness community managers and experts).

The company is now 40 employees predominantly in Austin with a small office in Peru. Since we last checked in, the company has transitioned to become a public benefit corporation, which Buhrdorf said was an attempt to better align the company’s charter with its mission orientation to help small business entrepreneurs.

Update: The funding total was changed from $10m to $15m. Sorry about that.

Kabbage, the AI-based small business loans platform backed by SoftBank and others, is adding more firepower to its lending machine: the Atlanta-based startup has secured an additional $200 million in the form of a revolving credit facility from an unnamed subsidiary of a large life insurance company, managed and administered by 20 Gates Management, and Atalaya Capital Management.

The money comes on the heels of a $700 million securitization Kabbage secured just three months ago and it is notable not just for its size but its terms: it’s a four-year facility, a length of time that underscores a level of confidence in the company’s performance.

Kabbage, which loans up to $250,000 in a single deal to small and medium businesses, has built a platform that harnesses the long tail of big data from across the web. It uses not just indicators from a company’s own public activities, but also sources comparative information from across a wider group of similar companies, with “2 million live data connections” currently helping to feed its algorithm.

Together, these help Kabbage determine whether to provide the loans, and at what rates. Notably, the whole process takes mere minutes, making Kabbage disruptive to the traditional route of applying for loans from banks, which can come at higher rates, often take longer to close and may never get approved.

The company was last valued at $1.2 billion in its most recent equity round from the Vision Fund in 2017, with about $500 million raised in equity to date from it and other investors, including BlueRun Ventures and Mohr Davidow Ventures. Rob Frohwein, the co-founder and CEO, confirmed to me via email that there are “no plans on the equity side right now.” We’ve asked about IPO plans and will update if we learn anything more on that front.

More importantly, alongside its equity story is the company’s business story: Kabbage has to date loaned out $7 billion in capital — amassed through securitizations and other facilities alongside that — to 185,000 businesses, and the company has seen an acceleration of business activity over the last two years. Nearly $700 million was loaned out in Q2 of this year, passing the record in Q1 of $600 million. This puts Kabbage on track to loan out between $2.4 billion and $3 billion this year.

“This transaction further diversifies Kabbage’s committed sources of funding and prepares us to meet the escalating demand for capital access among small businesses,” said Kabbage head of Capital Markets, Deepesh Jain, in a statement. “2019 has proven to be a tide-shifting year as customers accessed more than $670 million from Kabbage in Q2 2019, well surpassing our previously set record last quarter.”

While a lot of Kabbage’s business has come out of its direct consumer relationships, it’s also been expanding by way of more third-party relationships. It has white-label partnerships with banks to power their own loan offerings for SMBs, and earlier this year it was also tapped by e-commerce giant Alibaba to provide loans to its small business customers of up to $150,000 to help finance purchases, part of the latter company’s redoubled efforts to build out its business in the U.S. by way of its quiet acquisition of OpenSky.

Skedulo, a service that helps businesses manage their mobile employees, today announced that it has raised a $28 million Series B funding round led by M12, Microsoft’s venture fund. Existing investors Blackbird and Castanoa Ventures also participated in this round.

The company’s service offers businesses all the necessary tools to manage their mobile employees, including their schedules. A lot of small businesses still use basic spreadsheets and email to do this, but that’s obviously not the most efficient way to match the right employee to the right job, for example.

“Workforce management has traditionally been focused on employees that are sitting at a desk for the majority of their day,” Skedulo CEO and co-founder Matt Fairhurst told me. “The overwhelming majority — 80 percent — of workers will be deskless by 2020 and so far, there has been no one that has addressed the needs of this growing population at scale. We’re excited to help enterprises confront these challenges head-on so they can compete and lean into rapidly changing customer and employee expectations.”

At the core of Skedulo, which offers both a mobile app and web-based interface, is the company’s so-called “Mastermind” engine that helps businesses automatically match the right employee to a job based on the priorities the company has specified. The company plans to use the new funding to enhance this tool through new machine learning capabilities. Skedulo will also soon offer new analytics tools and integrations with third-party services like HR and financial management tools, as well as payroll systems.

The company also plans to use the new funding to double its headcount, which includes hiring at least 60 new employees in its Australian offices in Brisbane and Sydney.

As part of this round, Priya Saiprasad, principal of M12, will join Skedulo’s board of directors. “We found a strong sense of aligned purpose with Priya Saiprasad and the team at M12 — and their desire to invest in companies that help reduce cycles in a person’s working day,” Fairhurst said. “Fundamentally, Skedulo is a productivity company. We help companies, the back-office and mobile workforce, reduce the number of cycles it takes to get work done. This gives them time back to focus on the work that matters most.”

People should get paid for work they have done. It’s a pretty simple principle of capitalism, but a principle that seems increasingly violated in the modern economy. With semi-monthly paychecks, the work an employee does on the first day of the month won’t be paid until the end of the third week — a delay of up to 21 days. That delay is despite the massive digitalization of bank transfers and accounting over the past few decades that should have made paychecks far more regular.

Gusto, a payroll and HR benefits provider focused on small businesses, announced the launch of Flexible Pay today, a new feature that will allow its payroll users to select when they receive their income for work already completed. The feature, which must be switched on by an employer, will cost employers nothing out-of-pocket today. The launch is limited to customers in Texas, but will expand to other states in the coming year.

As Gusto CEO Joshua Reeves explained it to me, a kid mowing lawns in a neighborhood has a much more visceral connection to income than the modern knowledge economy worker. Cut the grass, get cash — it’s that simple. He also pointed out, with irony, that terminated employees experience much better payroll service than regular employees: they have to be paid out on their last day of work outside of the standard paycheck schedule. Reeves and his team wanted to offer that flexibility and convenience to every worker.

Flexible Pay allows users to choose when they get paid, outside of typical paycheck schedules

The key to this new feature has been Gusto’s increasing data about small businesses. Gusto now serves 1 percent of all small businesses in the U.S., and it has comprehensive access to its customers’ financial and payroll data. With integrations to time sheet services and proper risk modeling, Gusto is able to predict exactly what salary a worker has already earned, and can front the money at minimum risk to itself.

One major challenge for Gusto was how to reconcile the books of the employer with the irregular paycheck schedules desired by employees. Gusto handles all the logistics transparently, including tax withholding, so that for employers, the paycheck distribution looks and feels “normal” on its books.

That means that Gusto is effectively loaning money to companies, since it is paying payroll in advance. Gusto is funding those loans off its balance sheet today, but over time, the company expects to create a financial facility to underwrite the product.

For Reeves, Flexible Pay is “the right thing to do.” He believes that this new level of flexibility will empower workers to control their financial lives. In the long run, as more users get habituated to the product and its convenience, he hopes that the feature will draw other employers into using Gusto based on employee demand.

The unfortunate reality in the American workforce is that huge numbers of workers live paycheck-to-paycheck, by some counts as many as 80 percent. A bill can come due just a day or two before a paycheck hits, but without cash in a checking account, people often have to resort to predatory financial products like payday loans or high-interest credit cards in order to make ends meet. Flexible Pay is one step in the right direction of fighting for workers to get the money they justly deserve.

 Microsoft 365 lets businesses subscribe to a bundle with Office 365, Windows 10 and the company’s mobile device management tools. The early focus for this program was enterprises, but a few months ago, the company also launched a preview version of Microsoft 365 for small and medium businesses. Today, Microsoft 365 Business is coming out of beta and is now generally available to… Read More

 Kabbage, a company with some 115,000 customers and $3.5 billion in loans that has built an automated platform for lending money to small businesses and individuals using a large set of data points to determine a customer’s credit score, is announcing some big cabbage of its own today. SoftBank Group is investing $250 million in Kabbage — funding that Rob Frohwein, the co-founder… Read More

 In the shadow of its Inspire partner conference, Microsoft today launched in preview three new tools for small businesses: Microsoft Connections, Microsoft Listings and Microsoft Invoicing. These join the company’s existing stable of small business tools like Microsoft Bookings and the Outlook Customer Manager. Microsoft Connections allows its users to create Mailchimp-like email… Read More

 Main Street Hub, a company that helps mom and pop businesses run social media marketing, customer relationship management (CRM) and marketing automation recently announced it has received $20M in debt financing from Silicon Valley Bank. The company has raised a total of $40M. The most recent funding before this announcement was $14M in Series B in January, 2014. It has 6000 subscribers who… Read More