Tyler Maldonado
Stories by Tyler Maldonado
FINANCE
Investing in Athletes is Legal Now and Barely Anyone Does
Agentiq, Finlete and FANtium sell SEC-registered shares in a pro athlete's future paychecks. The filings show how the payouts work, and how…
FINANCE
How to Invest in Y Combinator Startups for $25 a Share
Robinhood's RVII fund listed August 13 at $25 and opened at $22.50. Here's what you actually own, what the 2-and-20 fee stack…
GROW
How to sell a micro SaaS business for 5.96x, not 2.24x
Flippa's H1 2026 data shows the average micro SaaS sale fetching 2.24x profit while top-quartile deals in the same price band clear…
FINANCE
VC Pitch Meeting Red Flags That Actually Predict a Pass
A partner slept through Liz Wessel's Series A pitch and her team got a term sheet two hours later. In-room energy tells…
FINANCE
What is a Down Round and What it Does to Your Team
Down rounds fell to 11.4% of priced rounds in Q1 2026, the lowest since 2019. Here's what actually happens to your cap…
FINANCE
Athlete Investing Collectives Want a Seat on Your Cap Table
CHAMP is reported to be raising $500 million with 250-plus athletes behind it, but the official announcement never named a dollar figure.…
GROW
How Much Do Newsletters Make When 0.62% of Readers Pay
beehiiv analyzed thousands of paid publications. The median newsletter converts six readers per thousand, and the niche you pick moves revenue more…
FINANCE
How WHOOP Makes Money Selling a 99 Membership
WHOOP gives away the hardware and charges an annual membership. That subscription flip took it from near-bankruptcy in 2017 to a 0.1…
NEWS
Why OpenAI is Delaying its IPO to Chase Trillion
Altman won't list below a trillion dollars. The founder lesson is about timing leverage, not finance.
HUSTLE
How Elon Musk Became the First Trillionaire
At 9:30 a.m. Eastern on June 12, 2026, Elon Musk became the world’s first trillionaire. A ticker symbol appeared on Nasdaq for…
GROW
How to Make Money With Pickleball in 2026
From coaching at 0-50/hr to facilities pulling 30-40% margins, here are 9 real ways to profit from pickleball, ranked by what actually…
GROW
How Much Do Podcasters Make in 2026?
From bash to 20 million a year, podcast earnings depend on downloads, niche, and how many revenue streams you stack. Here are…
FINANCE
Celebrity VC Investors 2026: Who’s Actually Moving Markets
Sound Ventures, Liquid 2, Serena Ventures, CHAMP, and the rest of the 2026 celebrity VC roster ranked by real portfolio returns and…
HUSTLE
Should YC Founders Take OpenAI’s M Token Deal?
OpenAI offered every YC Spring 2026 startup M in API tokens for equity via an uncapped SAFE. The equity math favors founders,…
FINANCE
What Is the CHAMP Fund and Why Founders Should Care
L Catterton and Patricof Co launched a 00M fund where 250+ athletes co-own brands instead of endorsing them. Here's how the economics…
FINANCE
How Founders Keep Control After an IPO
SpaceX's S-1 reveals how Elon Musk holds 79% voting power with 42% equity. Here's how dual-class shares work and what early-stage founders…
GROW
Top 8 Events to Attend During New York Tech Week 2026
New York Tech Week 2026 runs from June 1–7, 2026, bringing together founders, investors, operators, engineers, creators, and startup leaders across the…
GROW
Shopify Q1 2026 Earnings and What They Mean for Merchants
Shopify stock dropped 15% after record Q1 results. The platform itself has never been stronger for founders and sellers.
FINANCE
Y Combinator Just Made Its First Stablecoin Investment
YC paid prediction markets startup Totalis $500,000 in USDC on Solana. Now any YC-funded startup can opt for stablecoin payouts. Here is…
FINANCE
How Much Do Coachella Performers Get Paid in 2026
Justin Bieber's record $10M deal tops a pay structure where headliners earn millions and emerging acts often lose money. Here's the full…