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An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

NewslettersTerm Sheet

Defy Ventures teaches entrepreneurship in prisons. It changed how I think about founders

Allie Garfinkle
By
Allie Garfinkle
Allie Garfinkle
Term Sheet Editor
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Allie Garfinkle
By
Allie Garfinkle
Allie Garfinkle
Term Sheet Editor
Down Arrow Button Icon
February 20, 2026, 6:40 AM ET
Defy Ventures's Andrew Glazier.
Defy Ventures's Andrew Glazier.Defy Ventures

I love going to prison with Andrew Glazier. 

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Glazier is the CEO of Defy Ventures, a Los Angeles-based nonprofit running entrepreneurship training programs in prisons across eight states. And twice now, I’ve tagged along at Defy events, including a New York coaching day and a California pitch competition. As you might expect, there are all sorts of rules in prison: first names only, no promises, no asking ‘what you’re in for,’ high-fives and fist bumps. But I’d argue there’s one rule that matters above the others: That this is fundamentally humanizing. 

“When you walk into a Defy class, the first thing we’re expressing to you is that you’re a human with unique gifts and talents,” said Glazier, who’s run the organization since the founder’s departure in 2018. “You’re no longer ‘inmate number blank.’ You’re now an entrepreneur-in-training. What do you want to do?”

Entrepreneur-in-training (or EIT) is an important turn of phrase at Defy—there are no “convicts” or “inmates,” just EITs and volunteers. And I should say: I’ve shown up to these events as a volunteer, not as a journalist. But—as a person who interviews entrepreneurs and investors for a living—I asked Glazier if I could write about Defy, and what it reveals about entrepreneurship itself. 

As it turns out, even in prison, a pitch is a pitch and a business is a business. 

“Legal and illegal businesses involve the same skill sets,” said Glazier. “They require thoughtfulness around cash management, followership, marketing, inventory management, operations. So, for us, it’s about how you transform that hustle… We’re looking to employ entrepreneurship as a transformational frame.”

These pitches from EITs are often good to great, and frankly make more sense than half the startup pitches that hit my inbox each day. Unlike startup founders (kidding, mostly), EITs have rules for the businesses they’re proposing—there needs to be a clear customer problem you’re solving, a minimum viable product, a plan for overhead costs, and a possible path to scale. They’re simultaneously preparing for the reality that they’ll have to talk about the worst transgressions of their lives.

“It’s about leading with, ‘look I made some mistakes and these are some of the things I’ve learned through really hard times,’” said Glazier. “‘I’ve come out on the other side, and I can be a great asset to you and this community.’”

If you strip it all away, what’s the real difference between an EIT and the startup founders I talk to every day? In many cases, I’d argue it’s not talent, ideas, or grit. It’s opportunity and context. An entrepreneur is someone who has decided, for whatever reason, to control their destiny.

“Certainly, entrepreneurship for people coming home from prison can be a path to economic independence,” said Glazier. “When you come home, getting hired can be hard, advancement can be constrained. So, the idea that you can come home and be your own boss can be very compelling.”

And here’s the thing: The goal isn’t necessarily that every EIT will start their own business. Rather, the goal’s that they have a path back to the world, and to a better version of themselves. There’s evidence this program is deeply effective: 85% of released grads are employed within six months, and the one-year recidivism rate is less than 10% (nationally, that number’s more than 40%).

So, something’s working, and here’s my guess: That there’s something about entrepreneurship that is essentially and undeniably human—the ability to imagine a future that doesn’t yet exist, and to build toward it.

And that every founder, no matter where they are, is engaging in an expression of freedom.

See you Monday,

Allie Garfinkle
X:
@agarfinks
Email: alexandra.garfinkle@fortune.com
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VENTURE CAPITAL

- Code Metal, a Boston, Mass.-based code translation platform for mission-critical industries, raised $125 million in Series B funding. Salesforce Ventures led the round and was joined by Accel, Cap B, and others.

- Braintrust, a San Francisco-based developer of AI monitoring technology, raised $80 million in Series B funding. ICONIQ led the round and was joined by Andreessen Horowitz, Greylock, and others.

- Altesa BioSciences, a College Park, Ga.-based pharmaceutical company focused on therapies for COPD and asthma, raised $75 million in Series B funding. Forbion led the round and was joined by Sanofi and existing investors.

- ProSomnus Sleep Technologies, a Pleasanton, Calif.-based developer of non-CPAP sleep apnea devices, raised $38 million in funding from Catalio Capital Management.

- VIZZIA, a Paris, France-based provider of video surveillance technology for public safety and cleanliness, raised €30 million ($35.3 million) in Series B funding. Base10 Partners led the round and was joined by Headline and Sistafund.

- Circuit, an Austin, Texas-based developer of AI technology designed for manufacturing and service companies, raised $30 million from Jim Breyer, Charlie Amato, and other individual investors.

- Eagle Wireless, a Cleveland, Ohio-based Internet of Things and automotive solutions company, raised $30 million in Series B funding. Asymmetric Capital Partners and The O.H.I.O. Fund led the round.

- Portkey, a San Francisco-based developer of a platform designed to get AI systems ready for production, raised $15 million in Series A funding. Elevation Capital led the round and was joined by Lightspeed.

PRIVATE EQUITY

- Amberjack Capital Partners acquired CIMA Services, a Pasadena, Texas-based waste management, environmental remediation and industrial services company. Financial terms were not disclosed.

- Ariel Alternatives acquired Front Line Power Construction, a Rosharon, Texas-based powerline construction company. Financial terms were not disclosed.

- Bregal Sagemount acquired a majority stake in Harbor Compliance, a Lancaster, Pa.-based compliance solutions provider for nonprofit and middle-market corporations. Financial terms were not disclosed.

- Centralis, backed by HGGC, acquired PINE Advisor Solutions, a Denver, Colo.-based provider of compliance, fund officer, and distribution services to asset managers. Financial terms were not disclosed.

- CUBE, backed by Hg, acquired 4CRisk.ai, a San Francisco-based regulatory technology company. Financial terms were not disclosed. 

- Greenbriar Equity Group agreed to acquire AIT Worldwide Logistics, an Itasca, Ill.-based freight-forwarding company. Financial terms were not disclosed.

- Impact XM, a portfolio company of The Riverside Company, acquired Jack Morton, a Boston, Mass.-based brand experience and live event marketing agency. Financial terms were not disclosed.

- OceanSound Partners acquired Automated Financial Systems, an Exton, Pa.-based provider of loan servicing and lifecycle management technology for financial services companies. Financial terms were not disclosed.

- WestView Capital acquired a minority stake in Benefits All In, a Cincinnati, Ohio-based employee healthcare benefit and risk management company. Financial terms were not disclosed.

OTHERS

- eBay agreed to acquire Depop, a London, U.K.-based secondhand fashion marketplace, from Etsy for approximately $1.2 billion in cash.

IPOS

- Clear Street Group, a New York City-based capital markets infrastructure company, withdrew plans to raise up to $364 million in an offering of 13 million shares priced between $26 and $28 on the Nasdaq.

FUNDS + FUNDS OF FUNDS

- HGGC, a Palo Alto, Calif.-based private equity firm, raised $3.2 billion for its fifth fund focused on middle-market companies in the tech, business services, financial services, and consumer sectors.

PEOPLE

- DCVC, a Palo Alto, Calif.-based venture capital firm, promoted Rachel Slaybaugh to general partner. 

This is the web version of Term Sheet, a daily newsletter on the biggest deals and dealmakers in venture capital and private equity. Sign up for free.
About the Author
Allie Garfinkle
By Allie GarfinkleTerm Sheet Editor
LinkedIn iconTwitter icon

Allie Garfinkle is a senior writer and editor at Fortune, where she runs Term Sheet; leads coverage of private capital, investors, and startups; and co-chairs the Brainstorm conference series.

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