Michael O'Brien 🌻

Lobbyist-turned-Venture Capitalist | Government Relations Expert

@siol_vc | @MOB_Advocacy

[Michael O'Brien 🌻 @signed_MOB]

If you distill @Siol_VenCap's thesis down to three words the would be

REGULATION AS ALPHA

I think I can thank a 3 hour WhatsApp text conversation with @boardyai to come up with that.

[Síol Venture Capital @Siol_VenCap]

1/6 “Move fast and break things” worked for photo apps. But if you’re decarbonizing the grid or revolutionizing healthcare, breaking things gets a cease-and-desist, not a billion users.

In 2026, the real upside is in the toughest markets.

[Michael O'Brien 🌻 @signed_MOB]

Love this new tool from @delvedeeperai. Saves a ton of time, and have already seen actionable insights. Ask me if interested!!

https://t.co/YEZHlrkUaQ

[Michael O'Brien 🌻 @signed_MOB]

Funding that startup allows them to own 2 markets, and puts them years ahead as other markets open.

Regulation is not friction. Regulation IS Alpha!

[Michael O'Brien 🌻 @signed_MOB]

At the @Orrick HealthTech Summit, a VC on the panel asked how do you underwrite risk when a startup can only operate in UT and TX. He argued you can't.

I say he's wrong.

[Michael O'Brien 🌻 @signed_MOB]

At @Posinelli for @NewYorkTechWeek listening to Mike Borfitz talk about building in regulatory industries: Start w/ mission. Find someone who knows that mission & all the regulatory details. Then build it. That's it.

It's that easy ... AND that hard.

#RegulationAsAlpha

[Michael O'Brien 🌻 @signed_MOB]

Mr. Mayor - bedtimes are great but ... bring back outdoor watch parties (@NYCMayor) ... Let's go Knicks!

[Mayor Zohran Kwame Mamdani @NYCMayor]

Today, I signed an Executive Order temporarily repealing bedtimes in the City of New York so that kids of all ages can watch our team in the NBA Finals.

As Mayor, you’re forced to make many difficult decisions. This was not one of them.

Go Knicks.

[Michael O'Brien 🌻 @signed_MOB]

Super excited about this. I have been a fan of @ericries since reading The Lean Startup.

Q - is it wrong to ask an author to sign an old book at the event promoting his new book?

[Michael O'Brien 🌻 @signed_MOB]

If you follow my substack or LinkedIn ... you know I have been writing about "policy-market fit" for the last two weeks.

A couple weeks ago, DC City Council introduced an AV rideshare bill that allowed me to do a masterclass in real time.

[Síol Venture Capital @Siol_VenCap]

What is our take on the action of DC City Council and how it applies to "policy-market fit" and "regulation as alpha"?

DC’s New AV Bill - Autonomous Vehicles Didn’t Stall Because of Technology. They Stalled Because the Market Wasn’t Open.

Substack link in comments.

[Michael O'Brien 🌻 @signed_MOB]

This @BColon40 homerun is one of my favorite @Mets memories of all time. Sadly ... special moments like this may never happen again. #LetPitchersHit #LFGM

[New York Mets @Mets]

10 years ago today, the impossible happened.

@BColon40 | #LGM

[Michael O'Brien 🌻 @signed_MOB]

Happy #OpeningDay Eve. Much like parents who chose to ruin Christmas, evidently we get to open a crappy present tonight (sorry @Yankees fans) before we get to see the @Mets tomorrow. #LFGM

[Michael O'Brien 🌻 @signed_MOB]

@H2Colby Hey Colby. Would love to hear more.

[Michael O'Brien 🌻 @signed_MOB]

Happy St. Patrick's Day to those that celebrate ...

For those not in the know ... Síol is Irish for seed and I chose the name to keep early-stage startups as our North Star.

[Síol Venture Capital @Siol_VenCap]

They call it the 'Luck of the Irish.' We call it grit. ☘️

Building a startup isn't about finding a pot of gold; it’s about manufactured resilience. At @SiolVC, we know the best luck is built, not found.

Happy St. Patrick's Day to the global Irish founder network! 🇮🇪

[Michael O'Brien 🌻 @signed_MOB]

@IsaiahMears Would love an invite. The addresses on the site came up undeliverable.

[Michael O'Brien 🌻 @signed_MOB]

We’re seeing more family offices ask this exact question: if venture is now a core allocation, where does the next wave of alpha come from?

[Síol Venture Capital @Siol_VenCap]

Over the past decade, venture capital has evolved from a niche allocation to a core strategy for family offices and high-net-worth investors. According to recent data, venture allocations have grown from 17% of portfolios in 2015 to roughly 31% today.

https://t.co/6jDufCJjmX

[Michael O'Brien 🌻 @signed_MOB]

Excited for what we are building at @Siol_VenCap. Follow us.

[Síol Venture Capital @Siol_VenCap]

At Síol, we start at the beginning - a true pre-seed fund and firm. We’re here to plant ideas and help founders grow them into something massive. Excited to share our new look that captures that journey from sprout to scale. 🌱🚀 #VentureCapital #Startups #Growth

[Michael O'Brien 🌻 @signed_MOB]

After a bit of a snafu, the firm is back on @X. And now that we are close to closing Fund I, I feel better about sharing what we are building at @Siol_VenCap.

Follow Síol to follow along.

[Síol Venture Capital @Siol_VenCap]

People ask why we named the firm ‘Síol.’ (Spoiler: It’s not just for the aesthetic).

It’s Old Irish for ‘seed.’ 🌍🌱 Because we don't just write checks: we help daring founders plant the seeds for a world-changing future.

The 'Why' behind it all. 1/6 🧵

[Michael O'Brien 🌻 @signed_MOB]

One of my favorite childhood memories.

[SNY @SNYtv]

39 years ago today, the 1986 Mets were World Series Champions.

[Adeo Ressi @adeoressi]

Your government just announced another billion-dollar startup initiative.

Spoiler: It will fail spectacularly.

Over-regulated. Over-funded. Over-influenced. The holy trinity of ecosystem destruction.

Estonia gives local VCs money and walks away. Singapore backs regional investors without micromanaging. Israel trusts its talent to make decisions.

Guess who wins?

Local investors beat government programs every single time.

Give talented locals money with zero strings attached. Watch them build what bureaucrats never could.

Local investors beat government programs every single time.
They back the right founders. They create real ecosystems.

If you want to change what your government is doing wrong, I want to help. Let’s discuss.

[Michael O'Brien 🌻 @signed_MOB]

@bgurley As a former state lobbyist, I concur. But few startups have the ability, understanding or resources to change this, esp at the state level. It's why I pivoted from lobbying into VC.

[Michael O'Brien 🌻 @signed_MOB]

@jefielding Founder in residence for a year or two at a VC firm while he figures it out?