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Tax law

Use IRS Code Section 1202 to sell your multi-million dollar startup tax-free • ZebethMedia

Vincent Aiello Contributor Spencer Fane attorney and business owner Vincent Aiello helps businesses solve legal problems to secure revenue flow and reduce business risks. Whoever said you can’t have your cake and eat it too should have called their accountants and lawyers first. These professionals often receive inquiries from founders, equity investment firms and venture capitalists looking for ways to save on or avoid capital gains taxes on future business sales. Both lawyers and accountants encourage clients to examine the tax savings offered by setting up a Qualified Small Business (QSB) C-Corporation at the initial business formation stage. Using a QSB can eliminate capital gains tax due on the future business sale if the company is established and stock issued pursuant to Internal Revenue Code Section 1202. Many startups often simply default to a robotic use of S-Corporations, partnerships, and LLCs, but savvy tech founders should consider the excellent long-term tax savings afforded by IRS Code Section 1202. This article provides a general overview concerning the major requirements and tax savings provided by forming a startup entity structured to maximize the capital gains tax exclusion in IRC 1202. IRC 1202 excludes capital gains tax realized on the sale of qualified small business stock (QSBS) of non-corporate taxpayers if the stock has been held for more than five years. QSBS is stock in a C-Corporation originally issued after August 10, 1993, and acquired by the taxpayer in exchange for money, property or as compensation for services. The corporation may not have gross assets in excess of $50 million in fair market value at the time the stock is issued. The IRC 1202 gain exclusion allows stockholders, founders, private equity and venture capitalists to claim a minimum $10 million federal income tax exclusion on capital gains for the sale of QSBS. Prior to 2010, only part of the capital gain on QSBS was excluded from taxable gain under section 1202 and the portion excluded from gain was an item of tax preference subject to alternative minimum tax. This rule was changed for stock acquired after September 27, 2010, and before January 1, 2015, such that the gain on such stock was fully excluded and no portion of the gain was an item of tax preference. This change was made permanent by the Protecting Americans from Tax Hikes Act of 2015, signed into law on December 18, 2015. Given the changes to IRC 1202, it constitutes a significant tax savings benefit for entrepreneurs and small business investors. However, the effect of the exclusion ultimately depends on when the stock was acquired, the trade or business being operated, and various other factors. Qualifying for Section 1202’s capital gains tax exclusion takes careful planning The critical plan to be determined at the outset is the future stock sale, which must be structured as a sale of QSBS for federal income tax purposes to achieve capital gains tax exclusion. This can be a challenge, as buyers typically prefer asset acquisitions permitting a step-up in basis and future goodwill amortization. In many business sales today, buyers expect stockholders to roll over a portion of their equity, or receive stock or membership interests in a new entity as part of the transaction. Imprecise planning will cause the QSB stockholders to forfeit the QSBS gain exclusion and owe tax on the sale. This can happen if there is an impermissible equity rollover to an LP, or receipt of LLC equity.

2022 R&D tax prep, social media for founders, managing remote teams • ZebethMedia

As director of Techstars’ startup pipeline, Saba Karim spends much of his time touting the ways entrepreneurs can benefit by joining an accelerator. But is it the right choice for every founder? After he posted a thread on Twitter offering several rationales explaining why some should definitely avoid them, I invited him to adapt it for a TC+ guest post we published yesterday. “Keep in mind that funding will solve your money problems, but it won’t solve everything else,” he writes. Full ZebethMedia+ articles are only available to membersUse discount code TCPLUSROUNDUP to save 20% off a one- or two-year subscription “You’ll still need to figure out how to acquire customers, find the best talent, build an incredible product, assemble a great advisory board and get to product-market fit.” His article confirms a suspicion I’ve long harbored: many entrepreneurs pursue accelerators so they can gain access to investors, score free publicity, or receive positive reinforcement for their idea. But none of those are determining factors for success. “If you’re not living and breathing your startup, you’re going to struggle anyway,” says Karim. If you have information, knowledge or experience to share that could help early-stage startup founders, investors and workers make better decisions, please review our submission guidelines and drop us a line. Thanks very much for reading, Walter ThompsonEditorial Manager, ZebethMedia+@yourprotagonist These founders landed early checks by being savvy about social media (L-R) Connie Loizos, Silicon Valley Editor, ZebethMedia, Nik Milanović, Founder, This Week in Fintech; General Partner, The Fintech Fund, Joshua Ogundu, CEO, Campfire and Gefen Skolnick, Founder, Couplet Coffee. Image Credits: Kelly Sullivan/Getty Images for ZebethMedia Is there a correlation between being extremely online and a founder’s ability to fundraise? According to three entrepreneurs Connie Loizos spoke with at ZebethMedia Disrupt, a social media presence that blends aspects of your business and personal lives can “make it easier to connect with investors and customers.” Nik Milanović (founder, This Week in Fintech), Gefen Skolnick (founder, Couplet Coffee) and Josh Ogundu (CEO, Campfire) talked about the benefits and downsides of using TikTok, Twitter and other platforms to build authentic personal and business brands. “I even tweeted yesterday that it was kind of not a good day as a founder, and it was really nice and people engaged with that,” said Skolnick. “I don’t believe in constantly showing that things are good. Some days things are just not good.” How to effectively manage a remote team during wartime Image Credits: Anna Fedorenko / Getty Images “There are a lot of studies about crisis management on the web, but none of them tell us how to manage a company during times of war,” according to Alex Fedorov, CEO and founder of Ukrainian startup OBRIO. Prior to Russia’s invasion, “our company had never seen a real crisis,” he writes in a post that presents the six methods his company used to maintain continuity while protecting workers. “Training to manage stress, anxiety and personal finances will help your employees build the needed knowledge and respond to tough situations.” 3 founders discuss how to navigate the nuances of early-stage fundraising Image Credits: Kelly Sullivan / Getty Images Founders who have raised funds for early-stage startups in the last year have generally had an easier time than people seeking Series A money (or later). Then again, “easy” is such a relative term. At ZebethMedia Disrupt, Rebecca Szkutak spoke to three entrepreneurs to learn more about how they adjusted their expectations and tactics as they approach investors during a downturn: Amanda DoAmaral, co-founder and CEO, Fiveable Arman Hezarkhani, founder, Parthean Sarah Du, co-founder, Alloy Automation Prepare to amortize: Inflation may spell doom for R&D tax expensing Image Credits: Fancy/Veer/Corbis (opens in a new window) / Getty Images The U.S. federal government has made R&D tax credits available for decades, but a major change set to take place this year will impact startups across the board. Previously, R&D expenditures could be expensed upfront, but now, “those expenses will need to be amortized over 5 years in the case of domestic research, and 15 years for foreign research,” according to tax attorney Andrew Leahey. Because so many startups “incur the bulk of their R&D costs in their first year of operation,” many could wait “the equivalent of a lifetime” to recover those expenses. High inflation has stalled efforts to repeal the amortization requirement, so Leahey shares several tactics companies can use “to prepare for the possibility of the rule coming into effect.” Remote work is here to stay. Here’s how to manage your staff from afar Image Credits: Kelly Sullivan / Getty Images Before the pandemic, most startup workers had the same experience on their first day: set up a new laptop, fill out some onboarding paperwork, then start gathering intel on the best places to grab lunch near the office. Now that so many teams are hybrid or fully remote, companies are learning the importance of fostering company culture and community from day one, a topic Rebecca Bellan delved into at ZebethMedia Disrupt with three experienced managers: Adriana Roche, chief people officer, Mural Deidre Paknad, CEO and co-founder, WorkBoard Allison Barr Allen, angel investor, Trail Run Capital “The biggest learning for us over the last three years was that it’s very difficult to really build expertise in a domain or a subject through Zoom,” said Paknad. How our startup made it through 2 recessions without relying on layoffs Image Credits: Aaron Black (opens in a new window) / Getty Images So far this year, about 45,000 tech workers have been laid off. If that’s hard to visualize, imagine a sold-out Mets game at Citi Field in New York City. Cutting staff is standard operating procedure during a downturn, but Sachin Gupta, who leads sales, marketing and general operations for HackerEarth, says his company has weathered two recessions without resorting to mass firings. “At any given time, our staff portfolio operates at about 90% of what we consider ideal,” he says. “Think of this like the distance

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