Tax Cuts & The Big, Beautiful Bill: A Trillion-Dollar Tightrope?

Week of May 26th, 2025

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STARTUPS

ROUNDS AND UNICORNS

  1. Airwallex (Fintech): Raised $300M (Series F + secondary) at a $6.2B valuation. Founded in Melbourne in 2015, now headquartered in San Francisco, Airwallex offers a global business payments platform

  2. Awardco (HR Tech): Raised $165M in Series B from Sixth Street and Spectrum Equity, reaching a valuation of over $1B. Based in Salt Lake City, Awardco provides employee rewards and recognition solutions

  3. LMArena (AI): Raised $100M in seed funding led by Andreessen Horowitz and UC Investments. Based in San Francisco, LMArena is building an open community platform for AI model evaluation

  4. Monarch Money (Personal Finance): Closed $75M Series B led by FPV Ventures and Forerunner Ventures. The Covina-based platform offers budgeting and financial planning tools for consumers

  5. Siro (Sales Tech): Raised $50M in Series B funding led by SignalFire. Based in New York, Siro provides a mobile app for tracking in-person sales performance

The 10-Year Trend At Series B (Crunchbase, 4 minute read)

Series B rounds remain one of the most revealing indicators of the startup funding environment. Startups at this stage are early enough to still carry risk but far enough along to show real traction. Over the past decade, Series B deal counts in the U.S. have remained relatively stable (between 600 and 900 annually), with few fluctuations outside of the 2021-22 market peak

  • While there are typically twice as many Series A rounds as Series B, the funding totals between the two stages are usually comparable

  • Total Series B investment, however, has varied more dramatically, peaking at $347 billion in 2021 before falling to roughly half that last year

  • Despite these shifts, Series B rounds generally capture about one-sixth of all VC dollars, although 2024 appears lower due to the $40 billion OpenAI outlier at later stages

Since 2023, 259 new unicorns have joined the Crunchbase Unicorn Board, collectively raising $130 billion and adding $605 billion in value. This brings the total to 1,586 private companies valued at $5.9 trillion, with $1 trillion in funding raised. Leading investors in these new unicorns include Sequoia Capital and Lightspeed Venture Partners, followed by Andreessen Horowitz, Accel, and Nvidia. The majority of these unicorns are U.S.-based, while 17% hail from China, where HSG (formerly Sequoia China) and Tencent were particularly active

  • AI and semiconductor startups dominate the list of highest-valued newcomers, with U.S. names like xAI, Perplexity, and Mistral AI

  • Mega funding rounds include xAI’s $6 billion raise and General Catalyst’s $3.6 billion across 10 investments over $100 million

  • Despite these valuations, liquidity remains limited, only 2% of these new unicorns have exited, with three IPOs and three acquisitions

ECONOMIC SNAPSHOT

On Friday, President Donald Trump reignited trade tensions by threatening to impose a 50% tariff on European Union goods starting June 1, 2025, citing stalled negotiations and accusing the EU of unfair trade practices. He criticized the bloc for trade barriers, VATs, digital service taxes, corporate penalties, and a $250 billion annual trade deficit with the U.S., although official data puts the figure closer to $236 billion

  • The announcement rattled markets, causing significant drops in both U.S. and European stock indexes

  • In response, EU officials emphasized their willingness to find a solution but reiterated their readiness to retaliate, having already prepared a $108 billion tariff plan

  • Trump also reignited pressure on Apple, threatening a 25% tariff if iPhones aren’t produced domestically, despite prior discussions with CEO Tim Cook

The U.S. House of Representatives narrowly approved a major tax and spending package that is expected to reshape fiscal policy while adding an estimated $3.8 trillion to the federal debt over the next decade, according to the Congressional Budget Office. From an investor’s perspective, the bill’s passage brings both relief and renewed uncertainty. For markets, the bill is a double-edged sword:

  • On one hand, the higher borrowing limit removes a major risk overhang and ensures continued government operations. On the other hand, it intensifies worries about long-term fiscal sustainability

  • The U.S. debt-to-GDP ratio is now at 124%, and interest payments already account for 1 in every 8 federal dollars spent, a share expected to rise

  • Investors have responded by demanding higher yields on U.S. Treasuries, with 30-year yields briefly topping 5%, their highest level since 2023

On Thursday, House Republicans narrowly passed a sweeping, 1,000+ page bill (215–214) that advances key elements of Donald Trump’s domestic agenda, including trillions in tax cuts and major reductions to federal safety net programs. The legislation extends the 2017 Trump tax cuts, eliminates taxes on tips and overtime (2026–2028), boosts the child tax credit temporarily, raises the SALT deduction cap, and expands deductions for older Americans, while phasing out many clean energy incentives from Biden’s Inflation Reduction Act

  • The bill imposes stricter work requirements for Medicaid recipients (80 hours/month by 2026) and SNAP beneficiaries, raising concerns that millions could lose access to vital services

  • To appeal to both fiscal conservatives and blue-state Republicans, the bill raises the debt ceiling by $4 trillion but offsets this through cuts to programs and new immigration fees, including the first-ever $1,000 asylum application charge, among others

  • While Trump celebrated the bill as a historic legislative win, Senate Republicans remain divided, signaling a difficult path forward

Major global investors are increasingly diversifying their bond portfolios beyond U.S. markets, driven by growing concerns over Donald Trump’s trade policies and America’s mounting fiscal deficit. The recent approval of Trump’s tax bill, expected to significantly increase public debt, and the volatility caused by his aggressive tariff measures have undermined Treasuries’ traditional status as a safe haven. Investment leaders from firms like Amundi and JPMorgan noted that while the dollar remains the world’s reserve currency, the appeal of U.S. debt is fading amid fears of fiscal “indiscipline”

  • Experts also pointed out that the dollar has dropped 8% this year, further eroding confidence in U.S. Treasuries

  • Bond managers are now looking to markets in Europe, Japan, and Australia, which offer attractive yields and more stable economic outlooks

  • Analysts warn that the U.S. could sustain a budget deficit of 6–7% of GDP, increasing Treasury issuance and potentially requiring higher yields to attract buyers

IPO & EXITS

After a long dry spell for venture-backed IPOs, the recent successful public listings of Hinge Health and MNTN Inc.—alongside strong debuts by Contemporary Amperex Technology Co. and eToro—have brought fresh optimism to Silicon Valley. These developments signal a possible reopening of the IPO window, following years of market turbulence since the 2022 correction, when valuations collapsed, SPACs imploded, and fundraising stalled

  • Venture capitalists, increasingly pressured to deliver returns amid a liquidity crunch, see these IPOs as much-needed relief

  • For example, Insight Partners turned its 2018 investment in Hinge into a near $400 million stake, highlighting the potential windfall

  • As VC firms struggle to raise new funds, the current IPO momentum may mark a critical turning point, if startups can seize the opportunity before the window closes again

WHAT A TIME TO BE ALIVE

In the United States, five years after the murder of George Floyd reignited national attention on racial inequality, Diversity, Equity, and Inclusion (DEI) initiatives are facing significant political backlash. This has prompted a shift in corporate strategy: rather than abandoning DEI entirely, many companies are rebranding their efforts to avoid controversy. For example, terms like “diversity” are being removed from job titles and internal programs in favor of more politically neutral language such as “culture,” “belonging,” and “wellbeing”

  • This shift comes amid mounting political pressure, particularly linked to the Trump administration’s actions to dismantle fairness policies

  • DEI has become so politically charged that employees from minority backgrounds in financial services report feeling “muzzled,” with 70% saying there has been little progress since 2020

  • Experts emphasize that while the language may change, the strategic importance of DEI remains

AI8 VENTURES HIGHLIGHT

The Illusion of Recovery - Venture Capital 2025

“We’re bringing wealth back to America. That’s a big thing... It takes a little time, but I think it should be great for us.”

Donald J. Trump - 45th and 47th U.S. President

We are living in a world defined by rapid and accelerating change, political, economic, social, and technological. This is not a typical business cycle. We are in an era shaped by powerful megatrends, with AI transforming industries, geopolitical shifts reshaping markets, and macroeconomic forces creating new uncertainties.

Just weeks before the 2024 election, The Economist described the U.S. economy as the “envy of the world.” After Donald Trump’s victory in November, markets initially anticipated controlled inflation, deregulation, and a less restrictive monetary policy. Fast-forward a few months to April 2025, and the optimism has faded. With capital markets reacting negatively to renewed trade war fears, over $5 trillion in market value were erased in a couple of days.

2025 opened with headlines proclaiming a venture capital comeback.

On paper, VC funding rebounded, driven by an unprecedented surge in AI investment. But beneath the surface, it’s a tale of two markets: one propelled by billion-dollar mega-deals in Artificial Intelligence, and another still struggling to regain traction amid macroeconomic uncertainty, investor hesitation, and a lingering liquidity crunch.

With Trump reigniting trade wars, tariffs reshaping global supply chains, and AI advancing at breakneck speed, it’s becoming harder than ever to place clear bets.

The real question is: what are you going to bet on?

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Happy reading,

8alpha.ai’s Research & Investment Team