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As a wave of state-level retirement mandates quietly rolls out across the country, most small businesses arent prepared. More than 30 states have proposed mandates that would require small businesses to offer a retirement plan, and 10 states already have active state-sponsored retirement plans. California, the largest state economy, is leading the charge. By the end of this year, all California businesses with at least one employee must offer their employees a retirement benefit, either a 401(k) or enrollment in the state-run CalSavers program. By the end of 2025, those that dont could end up paying fines of up to $750 per employee, with more penalties added annually until they comply. That would be troubling on its own. But in a recent Guideline survey of California small business owners, 75% werent familiar with CalSavers and 65% didnt know about the fines. While the intention behind the legislation is good, the execution is falling short. Expanding access to retirement savings is important. About 7.5 million Californians lack access to a workplace retirement plan, and most of them work for small businesses. But when 98% of firms in the state have fewer than 100 employees, poor execution turns into a statewide problem. Whats happening in California is just the beginning. For small business owners across the country, this is a preview of whats coming nextfrom hidden compliance traps to unexpected penalties. The result: Policies meant to help workers are instead creating confusion, compliance headaches, and financial risk for the countrys most vulnerable employers. A system designed without small businesses in mind Many small business owners I talk to want to help their employees and offer retirement benefits. But theyre also stretched thin, juggling HR, payroll, complianceand now, state-level mandates that come with little warning and even less education. In Guidelines survey, 70% of California small business owners said managing a 401(k) is too complex, and 51% said its too expensive. Yet most had never heard of the SECURE 2.0 tax credits, which can cover 100% of the administrative cost of a 401(k) for the first three years. Thats a clear failure in communication. So instead of unlocking access, these well-intentioned policies are creating traps: rules most businesses dont know about, with fines they can’t afford. The fine print matters Meanwhile, many small businesses are defaulting to state-run programs like CalSavers, which are designed to be a simple option, but not necessarily a long-term solution. These programs dont allow employer contributions and come with limited plan options. According to Guideline research, 47% of employers who tried CalSavers shared that their employees thought the set up and management were difficult to use. Thats why many employers nationally are opting to offer their own 401(k) plans instead. Its not because they have to, but because they want to attract talent, retain employees, and build long-term loyalty. When the playing field is levelmeaning tax credits, modern tech, and low-cost plans are accessiblesmall businesses can offer big-company benefits. What small businesses should do now Whether or not your state has a mandate, its worth paying attention to whats happening in California. Here are some helpful tips for any small business owner: Check your states retirement rules. You might be surprised to learn whats already in place. Consider your options. You dont have to default to a state-run program, especially when a private 401(k) could cost less than you think. Review federal tax credits. If you qualify, you might get your plan fully paid for over the next few years. Dont wait for a fine to start planning. Retirement benefits are becoming important, as a cost of doing business, and may provide a competitive edge in hiring. Mandates shouldnt be a minefield Retirement access can be critical. But when small businesses are blindsided by mandates, miss deadlines they didnt know existed, and face unexpected fines, were not expanding accesswere undermining it. For small businesses to succeed, we need to design policies with their reality in mind. That means better communication, simpler solutions, and real financial support, not just penalties. Because when small businesses thrive, so can their employees. Kevin Busque is cofounder and CEO at Guideline.
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E-Commerce
It’s not just youPride is a lot less corporate this year, and one company sees it as an opportunity to adjust how it serves the LGBTQ+ community during June. What was once a month full of colorful ads, temporary rainbow-hued logos, and big-name brands committing ad dollars and sponsorship money to Pride efforts throughout June, is now seeing big businesses dialing down their monetary support for Pride initiatives, fearing political backlash. Companies like Target, Walmart, PepsiCo, and Anheuser-Busch, have largely rolled back their pride-themed products and donations to pride-related events. But not all companies are pulling their pride initiativesand one New York brewery is taking an entirely different approach to how businesses actually show up for the LGTBQ+ community. This month, Williamsburg-based Brooklyn Brewery will be giving away 25 grants of $1,000 each to trans, nonbinary, or two-spirit New Yorkers. In an email to Fast Company, Brooklyn Brewery president Robin Ottaway said direct donations to members of a vulnerable communitywho overall had higher odds than their cisgender counterparts for income at or below 200% of the federal poverty levelfelt like a better way to use money that would typically go to ads. OR , —where 22%, or 1 in 5 LGBTQ+ adults in the United States live in poverty, compared to an estimated 16% of their straight and cisgender counterparts— We looked at what wed typically spend on advertising during Pride Month and realized that money could have a much more meaningful impact if it went directly to the people who need it most, Ottaway wrote. Instead of running flashy ads we are choosing to redirect that [money] into direct aid. For the effort, called Brooklyn Brewery Supports, the company is partnering with Angelica Christina, an LGBTQ+ activist who serves on the board of the nonprofit Stonewall Inn Gives Back Initiative. Christina has worked with the brewery in the past through the organization’s Certified Safe Space initiative, as well as for the brewerys Stonewall IPAwhich has been the official beer of NYC Prides events for the past three years. Trans folks, non-binary, and two spirit folks are often denied job opportunities or denied access to affordable housing,” Christina says. I am a formerly homeless person, and so I know how difficult it is to survive in such a large metropolitan city like New York, especially when you’re pushed into the brink of poverty. Christina is leading the effort’s outreach to the city’s trans community to get word out about the grants. She’ll ultimately help choose recipients and share their stories on social media, if they’re willing. To apply, people can either nominate themselves or someone else (21 or older) via a Google form that includes space to explain what a nominee plans to do with grant money. Christina notes that the money will ideally help recipients with rent, medical bills, groceries, and other basic needs. She says the brewery’s focus on direct aid and connection with the city’s LGBTQ+ community was what sold her on the partnership when Brooklyn Brewery approached her about it. There is not a day that goes by where Brooklyn Brewery does not support this community, Christina said. Whereas other corporations will put up a pride flag for Pride Month, but then for the rest of the year, we’re ignored.” View this post on Instagram A post shared by The Brooklyn Brewery (@brooklynbrewery)
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E-Commerce
If youre a founder, raising money is as high stakes as it gets. For a startup, capital can be the difference between scaling and failing. Ive raised rounds from under $1 million (yes, thats how things were done back in the day) to over $200 million, in timeframes varying from months, to a tightly orchestrated two weeks, to getting preempted with a term sheet. The lessons I learned from our hardest fundraise, our Series A, have stuck with me the most. I endured 29 nos before I heard a yes, and only in retrospect was it clear that it didnt have to be that way. I knew raising our Series A would be tough; I wasnt a lawyer and had no reputation as a founder, and hardly anyone was investing in the legal tech industry. This might be surprising today, with legal tech venture investments approaching $2 billion in Q1 2025 alone, but in 2015, legal tech was more of a curiosity than it was a software category. On the flip side, we had built a strong product and were on our way to a real business, with over $2 million in annual revenues. Some of the countrys top law firms and more than half of U.S. state attorneys general were using our e-discovery solution to quickly pinpoint key evidence in the millions of documents they reviewed during litigation and investigations. I put together a pitch that highlighted the tough problems we had solved and the big opportunity ahead. The need for experimentation As I drove up and down the highways of Silicon Valley in my 1999 Nissan Altima, pitching to venture capitalists (VCs), a pattern emerged. Rarely did I hear an immediate no; VCs were interested. I would be invited back for meetings with increasingly senior folks, only to eventually be let down for a variety of reasons: They didnt have an investment thesis about legal, the market wasnt big enough, and so on. But each one felt so close. I kept refining my pitch and delivery, squeezing out a bit more interest each time, seemingly just one meeting away from the golden ticket. I was wrong. Twenty-nine rejections later, there was no denying it. Somewhere in my Altima along Highway 101, with just a few names left on my list, I knew I had to change my approach. I realized I had made a big mistake: I had focused on refinement rather than experimentation. When a company is small, fundraising is intensely personal and emotionally daunting. If you cant raise money for the team, it feels like you are letting them down. This pressure yields an interesting dampening effect: Because raising is so critical, every meeting could be the one, so you feel compelled to deliver your best performance. Thus, as the rejections mounted, the stakes felt ever higher. Given the positive signals I had gotten in prior VC pitches, it felt reckless to risk that meeting with an experimental approach, so I delivered the practiced spiel that had gotten me so close in the pastwith the same results. Had I crashed and burned early on in the process, experimenting would have been obvious. Instead I was deluded by proximity to success. Fundraising is not a popularity contest; you dont need a lot of likes, you need one love. Rethink everything And that meant I had to rethink everything. Even if it meant lowering my chances of success in the next few pitches, I had to believe it would get me to a better overall outcome. If you asked me about technological disruption, I could have told you in a heartbeat that big changes rarely happen incrementally, but I hadnt generalized that lesson to business. Incremental improvement might work (for a while) if youre a market leader, but any other situation requires constant experimentation and reinvention to do your best. You have to be willing to take some short-term losses to earn bigger long-term gains, evenor especiallywhen it matters the most. When it came to raising money, it took me a mere 29 rejections to relearn this lesson. So I went for broke and restructured my entire pitch. Instead of trying to convince VCs about the opportunity in legal, I used analogies to industries they were much more familiar with, so that they could pattern-match better. Instead of showcasing all the rich functionality we had built (which, frankly, they didnt seem to care much about), I spoke more conceptually about our vision to build a platform in a space that didnt have one. In other words, instead of educating VCs about my language, I learned to speak theirs. Were these obvious and sensible changes? Yes. The revelation wasnt so much the changes I was making to the pitch, but their magnitude and my willingness to make them. After months of failure, I wasnt prepared for how quickly things improved. My new approach immediately resonated with VCs. Within a week, I had a term sheet from Andreessen Horowitz (a16z), one of the most reputable VCs. Now, a16z deserves plenty of credit: They had some experience with the legal process and understood its potential, and were one of the few firms that viewed my PhD in computer science more favorably than they would have the JD I didnt have. It was also clear that my new pitch struck a chord and framed the company in the right light; we sailed by the usual roadblock questions in the final meeting. With a16zs investment, we were off to the races. Nearly a decade later, our business serves more than 1,000 customers and brings in 9-figures of revenue a year. Its now clear how pivotal that raise was for our company. It was also a massive growth moment for me as a founder. It taught me to have an exploratory mindset, whether its to new product areas, markets, or technologies. Experimentation is at the heart of progress, and its essential when the stakes are the highest. AJ Shankar is founder and CEO of Everlaw.
Category:
E-Commerce
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