Managing Partner @ Social Leverage, Serial Entrepreneur, Husband & Father

San Diego, CA
Joined May 2007
Love this, let’s go!
if you think you fit this, send me a dm! i'm hiring for the sales team at Tabflows, $100–120k base, $200–240k OTE + generous equity we've been growing 10% week over week since August and want to hire the best of the best.
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Quite the run..
5 years since the tweet that changed my life forever…
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Gary Benitt retweeted
Today at Gusto Next, we unveiled new tools to help accountants build what's next — for their firms and the small businesses they serve: 👉 Leveled up Gusto Pro with new AI-assisted workflows 👉 Expanded the Gusto Partner Program to unlock more funding & support for firms 👉 Launched our new multi-client MCP, so accountants can connect Gusto to their favorite AI tools One idea behind all of it: we're building a future where our shared small business customers thrive — and helping our accounting partners grow alongside them. More: gusto.com/company-news/intro…
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Love to see more incredible products coming from @GustoHQ
HR and compliance keeping you up at night? We're launching 3 new features so you can get back to building your business: Business Compliance, HR Partners, and PEO. Because we already run your payroll, we see the moment you hire across state lines and handle what's required, plus give you HR support when things get complicated.
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A monumental milestone for @Fiscal_ai. @OpenAI has selected Fiscal AI as a Financial Data Provider for ChatGPT. This partnership gives financial professionals & individuals the ability to pull high quality financial data directly into ChatGPT for their research and analysis out of the box. Investment research with accurate structured data linked back to the source material right inside of ChatGPT is a game changer.  With this partnership, OpenAI’s newest models combine Fiscal AI's fundamental financial data which is updated with industry leading speed just minutes after release. ⚡
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Gary Benitt retweeted
We’ll be bringing prediction markets to Alpaca’s global brokerage infrastructure through our partnership with @Kalshi, the world’s largest prediction market exchange. Through the integration, we’ll offer CFTC-regulated event contracts via the same agent-first infrastructure partners and builders already use for stocks, options, fixed income, and crypto.
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Gary Benitt retweeted
The global online Alpaca AI Trading Agents Hackathon, co-hosted with @lablabai, is open for registration, with a $5,000 total prize pool and 3 winners. From August 28 to September 4, participants will build an autonomous AI trading agent using Alpaca’s Trading API and either Alpaca’s MCP Server or CLI. Join the Alpaca AI Trading Agents Hackathon by registering at lablab.ai/ai-hackathons/alpa… to view full terms and conditions.
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Gary Benitt retweeted
Data from the SEC shows that the proceeds from US IPOs reached $115.7 billion in Q2 2026. Since the turn of the century, only Q1 2021 surpasses it, recording a staggering $132.9 billion. Data includes SPACs.
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Gary Benitt retweeted
Get paid to do what you already do: talk about beehiiv. 💸 Our Partner Program lets creators earn up to 60% recurring commission for every paying customer they refer. Tomorrow, Partner Program Lead Joe Vargas breaks down how it works, shares best practices, and covers brand-new updates ending with a live Q&A. Day-one partner or partner-curious? This one's for you. 🗓️ Aug 19, 11AM EDT 🔗 in the thread!
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FCM registration is the real unlock here. Proud of the Alpaca team.
We’re excited to share that Alpaca’s subsidiary Alpaca Derivatives LLC has registered with the Commodity Futures Trading Commission (CFTC) as a futures commission merchant (FCM) and is now a Member of the National Futures Association (NFA).
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Amazing. This is the feature that actually makes legal AI trustworthy. Nicely done Nader and team.
Introducing Fact Extraction! Getting the facts right is the foundation of every case. We’re bringing back trust to litigation teams, and putting the experts back in the driver’s seat with Fact Extraction, our latest addition to newcase.ai
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Gary Benitt retweeted
Today is a Gusto Showcase! It’s one of my favorite moments, when we share a summary of how we’re making Gusto better for our 500,000+ small business customers. At @GustoHQ, we obsess over helping small businesses, and every challenge they face is an opportunity for us to help. Gusto has never been just a tool or technology. We strive to be a partner for small businesses, taking hats off their head, doing work on their behalf, so they can progress in building their business. With 500,000+ customers, we know we’re still early in the journey. There are millions of small businesses we are eager to serve. The future of business is small. And that’s big. #GustoShowcase
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So much fun building this, or more accurately orchestrating @claudeai to do the heavy lifting. Shows me that pretty much anyone could do anything that they want. It's a whole new world.
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Every AI company pitching "enterprise copilot" is going to lose to the ones building for a single job function. AI PM. AI SDR. AI recruiter. Depth beats breadth. The workflow is the moat.
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Watching @sama and @elonmusk battle it out legally here re OpenAI is a great time to showcase our fund 5 @SocialLeverage new portfolio company Newcase.ai Don't argue/sue/defend yourselves without it...
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Nobody breaks down the world of financial speculation quite like my biz partner @howardlindzon. The degenerate economy is global, inevitable…and a lot more fun than you think.
The Degenerate Economy - You Can't Escape It... Even In Venice Speculation is entertainment and a lifestyle and the South Koreans are leading the way... T-POP is the new K-POP fresh on my newsletter -link in thread
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Finally, I get to share this with the world! Cash flow keeps business owners up at night. That’s why I couldn’t be more excited about this launch. Today, we’re introducing 🔥 Gusto Money 🔥 —a suite of tools that gives small businesses the clearest view of their finances yet. We also unveiled: - Instant Pay for 24/7 payroll - Level-funded health plans that save ~20% - Gusto HR Partners for on-demand HR expertise - Payroll Hub to help accountants work faster This Showcase goes beyond features—it’s about giving small businesses control and confidence.
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Exciting Stocktwits news…
We are excited @stocktwits to be working with @polymarket and you will start seeing some awesome integrations soon, especially around earnings season Unlocking more data and flow and liquidity and alpha is what people want - more degenerate economy as retail likes to trade and invest
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Gary Benitt retweeted
1upHealth is currently seeking a Vice President of Engineering. This role requires a hands-on leader with deep technical expertise and proven success building and scaling distributed systems in cloud environments.☁️ Apply Here: bit.ly/3V8If3r #hiring #techhiring #jobs
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