co-founder @pennant_ai (s26) prev clawed da world @clawcon
San Francisco, CA
Joined May 2020
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Tommy retweeted
We’re proud to announce Pennant’s $5M seed round.
Thank you to our lead investor, Urban Innovation Fund, to @ycombinator, and to our many valued industry investors, partners and clients who are on this journey with us.
We’re hiring in New York City. If you want to build frontier AI with @0xtotaylor, @rywicks and the team at the cutting edge of corporate governance, helping investors and companies navigate decisions that shape trillions of dollars in public markets, we’d love to hear from you.
getpennant.ai/insights/seed-…
🤖 Made with AI
Tommy retweeted
The earnings call gets the headlines. The shareholder vote can change the company.
CEO compensation. Board control. Major corporate transactions.
Some of the biggest decisions at public companies are shaped through shareholder votes - but most people never see the work behind them.
@rywicks spent years inside that process.
At State Street, he met with boards and C-suites and helped the firm arrive at voting decisions as a major institutional shareholder.
Later, at PJT, he sat on the other side of the table, advising companies navigating those same investors.
And behind a single decision could be thousands of pages of SEC filings, third-party research and years of internal notes.
Ryan describes the workflow as “a total patchwork”
So he and his co-founder @0xtotaylor - who he’s known since undergrad and started alongside at BlackRock - built @pennant_ai
Pennant is building the corporate governance OS for institutional investors.
The platform brings meetings, filings, proposals, voting policies and decision records into one place - helping teams analyze and coordinate proxy voting, apply their own principles at scale and maintain a clear record of how decisions were made.
And because Ryan and Tommy spent years working with the exact people they’re now building for, their product bar is simple:
Would our former bosses and teammates use this day in and day out?
That mindset has shaped how they build.
Instead of guessing what customers need, the Pennant team spends time on the desk with institutional investors, starts with their biggest problem and builds from there.
Know the workflow deeply enough, and your former job can become your startup’s unfair advantage.
🎙️ @rywicks CEO & Co-Founder, @pennant_ai on @Fondocom @thestartpod
00:57 From BlackRock and State Street to building Pennant
01:27 The hidden governance layer behind public companies
02:05 Meeting Tim Cook as Nike’s compensation committee chair
03:47 How boards think about CEO pay and incentives
05:42 Why shareholder voting matters to institutional investors
06:08 The thousands-of-pages “patchwork” Pennant is replacing
07:18 Building software their former teammates would actually use
08:17 Why Pennant starts with each client’s biggest problem
Tommy retweeted
And that's a wrap on Demo Day! What a summer. Building @pennant_ai AI with @0xtotaylor , traveling all over the US to visit Pennant clients on the desk (and recruiting new ones), all while learning from our customers, fellow founders and leaders in the @ycombinator S26 cohort has changed the way I've approached starting a business.
Thank you to @bradflora and @ChristinaG325 for believing in us, the late night office hours that shifted our perspective, and the consummate guidance across strategy, sales, and much more.
And of course, a big thank you to our better halves, family, friends, mentors and clients, your support and partnership is why we do this.
I'm more grateful and energized than ever to be building this company and working towards our mission, and we're just getting started.
A lot more to come for Pennant in H2, stay tuned.
Tommy retweeted
What Is To Be Done?
I propose a simple plan:
Big AI companies should be allowed to build AI as fast and aggressively as they can – but not allowed to achieve regulatory capture, not allowed to establish a government-protect cartel that is insulated from market competition due to incorrect claims of AI risk. This will maximize the technological and societal payoff from the amazing capabilities of these companies, which are jewels of modern capitalism.
Startup AI companies should be allowed to build AI as fast and aggressively as they can. They should neither confront government-granted protection of big companies, nor should they receive government assistance. They should simply be allowed to compete. If and as startups don’t succeed, their presence in the market will also continuously motivate big companies to be their best – our economies and societies win either way.
Open source AI should be allowed to freely proliferate and compete with both big AI companies and startups. There should be no regulatory barriers to open source whatsoever. Even when open source does not beat companies, its widespread availability is a boon to students all over the world who want to learn how to build and use AI to become part of the technological future, and will ensure that AI is available to everyone who can benefit from it no matter who they are or how much money they have.
To offset the risk of bad people doing bad things with AI, governments working in partnership with the private sector should vigorously engage in each area of potential risk to use AI to maximize society’s defensive capabilities. This shouldn’t be limited to AI-enabled risks but also more general problems such as malnutrition, disease, and climate. AI can be an incredibly powerful tool for solving problems, and we should embrace it as such.
To prevent the risk of China achieving global AI dominance, we should use the full power of our private sector, our scientific establishment, and our governments in concert to drive American and Western AI to absolute global dominance, including ultimately inside China itself. We win, they lose.
And that is how we use AI to save the world.
It’s time to build.
Tommy retweeted
Scenes from last week's Corporate Governance Tech Summit, in proud partnership and with gratitude to the @Society4CorpGov Northern California, Nevada & Hawaii Chapter and to our generous hosts at @WorkOS . Thank you again to our panelists, every discussion lived (way) up to its billing and yielded great Q&A and follow-ups out the door in front of a packed house.
@ericries Ries - Incorruptible, The Lean Startup, @ltse
@evanepstein - Boardroom Governance
Marcy McCullaugh, Ph.D. - Parnassus Investments
Doug Sharp - @coinbase
Aaron Briggs - @gibsondunn
Robert Zivnuska - @PJTPartners
Ariel Smilowitz - @PwC Governance Insights Center
Drew Hambly - @CalPERS
Mary Catherine Malley - @HPE
Emmanuel Tamrat - @CouncilInstInv
Justin "J.T." Ho - @ClearyGottlieb
Peter Michelsen - @qatalystgroup
Zander Rosenbluth - Garden Investments
Jed Repko - Joele Frank
Tommy retweeted
Pennant is a very unique YC company. They sell to people that no YC company has done business with before: the tangle of consultants, investors, advisors and corporate executives trying to plan for and manage shareholder voting. Many billions of dollars change hands here and AI has made them buyers for the first time in decades.
Our team at @pennant_ai is building the Corporate Governance OS for the next age of public markets. We're proud and incredibly excited to be launching with @ycombinator today.
We know this market and the pain points we are solving for firsthand, and we are thrilled to be defining a new way forward.
Lots of hard work to get here and plenty more ahead, grateful to be on this journey with @0xtotaylor!
If you touch proxy voting, shareholder activism or corporate governance, and want to shake things up, let's talk.
getpennant.ai
Tommy retweeted
Our team at @pennant_ai is building the Corporate Governance OS for the next age of public markets. We're proud and incredibly excited to be launching with @ycombinator today.
We know this market and the pain points we are solving for firsthand, and we are thrilled to be defining a new way forward.
Lots of hard work to get here and plenty more ahead, grateful to be on this journey with @0xtotaylor!
If you touch proxy voting, shareholder activism or corporate governance, and want to shake things up, let's talk.
getpennant.ai
Tommy retweeted
I’m significantly older than you. I started coding in the late 60s. My current strategy is to not read any of the code written by my agents. That’s the only way I can take advantage of their productivity. What I do instead is to surround the agents with extreme constraints. Unit tests, gherkin tests, QA procedures, quality metrics, mutation testing, test coverage, and a plethora of others. In the end, I have very high confidence in the code they produce because they’ve had to run the gauntlet of all of my constraints and tests.
Tommy retweeted
What an incredible evening!
Thank you @dwarkesh_sp, @drfeifei and the hundreds of you who joined tonight.
It’s these kind of conversations that make SF special. 🌁❤️
Tommy retweeted
The founder in their 40s with taste and discernment is the new gentleman unicorn founder
Because there can be 100x to 1000x of them working at their beck and call via agents and software factories all the time
The age of the 40-year-old founder is back.
Bryant Chou spent 12 years as CTO of Webflow, which now powers something like 1.5% of the entire internet. He's back in the current YC batch with Ploy, an AI marketing platform, and he describes himself as "a bit of a boomer, double the age of the YC founders." But over 13% of his batch is already using his product, within months of launch.
There is a side of the argument which destroyed one of the main edges young founders have, which was being faster and cheaper at building.... speed is everyones game.
If what's left is knowing what to build this is more likely to come from spending 15 years watching an industry up close, collecting the thousand small frustrations that tell you where the real problem is. Bryant can build an anti-slop website tool because he spent over a decade learning exactly why websites are slop.
So I'm updating. I don't think it's young vs. old. I think AI rewards whoever has the most domain knowledge to point it at, and only sometimes is this younger founders who are thinking outside of the box...
Tommy retweeted
I was 37 when I started YC. It changed my company and my life.
I’m sharing that because a lot of founders quietly think they missed their window. Too old, too settled, should’ve done it at 25.
You haven’t missed it. The experience you think makes you late is often what lets you build.
