
Barbara Bickham | CTO Trailyn Ventures | AI, Blockchain, Deep Tech | Founder @TrailynVC | AI Strategy
Los Angeles, CA
Joined September 2008
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Barbara Bickham retweeted
Replying to @markgadala
Who could have known… “Traditional banking cryptography (RSA / ECC) is significantly easier to break into than either in flight or at rest Bitcoin.
If this is a risk to Bitcoin, it’s a far greater risk to the traditional banking industry. Banks are quick to point out that they could roll back and undo any such disaster, but that entire process is ripe for attack too.”
Read the full story at the-grain.org/writing/quantu…
Barbara Bickham retweeted
BREAKING: PHP, Node.js, GitLab and LiteLLM all had critical security incidents on the same day.
If you run production software, here's what to do this week:
1. Patch what faces the internet first.
> PHP: 8.5.12, 8.4.27, 8.3.36 or 8.2.35
> Node.js: the 21 October security releases for 22, 24 and 26
> Self-managed GitLab: the 21 October critical patch release
Attackers start with whatever answers on a public port.
2. Find anything on PHP 8.1 or older.
The PHP project won't fix it. Get a vendor backport or upgrade, and keep it off the public internet until you do. "We'll upgrade next quarter" is now an open door.
3. Search every environment for LiteLLM 1.107.0.
That release shipped a credential stealer. If it ran anywhere, rotate every cloud and model API key that machine could reach, then rebuild it. Removing the package isn't enough once the keys are gone.
4. Stop pulling "latest" this week.
Pin versions, commit your lock files and make CI install exactly what you reviewed. Supply-chain attacks count on the auto-update.
5. Update runtimes and package managers.
Node.js has already pulled the compromised eMudhra certificate from its trust store. Old versions still trust it.
6. Check the systems nobody owns.
The app nobody has touched in years and the server only one person knows about are where this week's bugs will still be live next month. If nobody owns it, nobody patches it.
If you own a portfolio of software companies, forward this to every CTO today.
$700B on AI infrastructure in 2026. Most of the funders won't capture the value.
Data center: 18–36 months to build. Grid hookup: ~5 years.
Value accrues to the constraint.
Silicon, agents, data or governance: what pays first?
Read Ch. 1: unbound.trailyn.com/
Quantum + Bitcoin:
6.4M BTC, including Satoshi’s 1.1M, could be exposed to a future quantum computer.
9 crypto firms just formed a Quantum Alliance to get ahead of it.
Real threat by 2028, or hype? 👇
unbound.trailyn.com
Stablecoins
Stablecoin payments: +45% this year.
Stablecoin supply: basically flat.
Same coins, moving faster through Visa, Mastercard and Stripe.
Invisible plumbing or real disruption? 👇
Unbound No 272: unbound.trailyn.com
Talent was never the problem.
Old patterns were.
Creativity is how you break them.
What's one talent you've been keeping on the shelf?
unbound.trailyn.com/awaken-y…
🚀 $102B invested in AI in Q3 2026. But what's actually working?
Join us Oct. 13 at 11 AM PT for real-world AI use cases, ontology vs. taxonomy, and practical implementation insights.
🎁 Exclusive PureBrain discount!
Register: luma.com/mgt3n6kn
Barbara Bickham retweeted
Resilience is the greatest driver of venture returns. But what kills companies is a lack of integrity in entrepreneurs, so we spend a lot more time on character than we used to.
I’m joining the Boardy Pro Advisory Board!
I’m working closely with @Boardyai and his team to shape the future of Boardy Pro.
Boardy gave me 5 invites to share: 1 year of free access to Boardy Pro.
Comment “BOARDY PRO” if you want in!
Barbara Bickham retweeted
BREAKING: a16z just released the 50 AI tools startups spend the most money on 😱
Want to know what the fastest-growing startups are actually using?
This is probably the closest thing you’ll find.
A few patterns stand out:
•OpenAI and Anthropic dominate the stack
•Cursor, Replit, and Lovable are making every team more technical
•Clay and Instantly are becoming standard for outbound
•Voice AI is everywhere (ElevenLabs, Otter, Krisp, Plaud)
•AI meeting assistants are turning conversations into searchable company knowledge
Barbara Bickham retweeted
Wow! Bots have now passed human traffic online for the first time in the Internet's history.
Welp, that happened faster than I predicted. Thought it would be end of 2027, then early 2027, but agentic traffic growing so fast that bots have now passed human traffic online for the first time in the Internet's history. radar.cloudflare.com/traffic…
Barbara Bickham retweeted
Very interesting!!
Starbucks fired its AI inventory tool and is going back to humans!!
seekingalpha.com/news/459603…
Here's YC's official advice about being truthful and precise about what is pilot, bookings, revenue and recurring revenue.
Founders, particularly first time founders, need to sear this into their brains. Don't mistake one tier for another. Be precise, and always be truthful.
One week until applications open for RAISE GP Day 2026!
This event is a skills-first day for emerging VC managers.
We're so proud to co-produce this RAISE GP Day alongside @VCForward and @raiseconference!
Learn more: events.raiseglobal.co/event/…
A few details:
📍 San Francisco
📅 October 21
🎟 300 GPs
📝 Apps open May 1
Barbara Bickham retweeted
Figuring out VC can feel like guessing your way through it.
There’s a lot of content, but few places where it’s actually taught in a practical way.
VC University was built to change that.
Early registration is open. 21 cohorts have sold out.
🔗venturecapitaluniversity.com…
Barbara Bickham retweeted
The scholarship application for Cohort 22 of #VCUniversity opens today! 🥳
If you’re an early-career or aspiring VC investor from an underrepresented background, we encourage you to learn more and apply by Friday, March 6: venturecapitaluniversity.com…





















