The Augment Exchange

Kyle Harrison learned venture three ways before he joined Contrary. TCV thought like private equity, Coatue like a hedge fund, and Index like classic venture. At Contrary he founded Contrary Research and co-wrote The Anduril Thesis: a hundred years of what broke in defense, and how Anduril’s founders sought to address those issues. He believes every company is a story, and “nobody is entitled to anyone else's wealth creation.” In this episode, Max sits down with Kyle Harrison, General Partner at Contrary. They discuss:- The Kill Chain: the carrier purchase that Congress could not cancel, and how cost-plus contracting can create incentives that Kyle argues may contribute to slower or more expensive procurement - From ~36% of global R&D to 1%: how the DOD lost the cutting edge, and who bought the first Sentry Tower- Frisbees at Ferraris: exquisite vs. attritable and the economics of war, a missile in the tens of millions against a carrier in the billions- Vannevar Bush's Memex to LLMs: the family tree from wartime research to AI- Defense investing: ethics, deterrence and market structure:  “just war” theory, deterrence math, and from the world's police to the world's gun storeABOUT THE GUESTKyle Harrison is a General Partner at Contrary and the founder of Contrary Research. He invested at TCV, Coatue, and Index Ventures before joining Contrary. He co-wrote The Anduril Thesis with Sachin Maini and writes Investing 101. Contrary is an investor in Anduril.LinkedIn: https://www.linkedin.com/in/kyle-harrison-9274b278 Company: contrary.comOUTLINE(01:31) Wedding videos to venture capital(11:56) Anduril's founders and the Lindy effect(15:26) Kill Chain, cost plus, Sentry Tower(28:33) Vannevar Bush, the Memex, and LLMs(33:59) Frisbees at Ferraris(40:31) Just war and propaganda(49:25) World's police to world's gun store(1:02:13) Lattice and mosaic warfareMENTIONED IN THIS EPISODEAnduril. The Anduril Thesis. Palmer Luckey. SpaceX. Stripe. Anthropic. OpenAI.FOLLOWMax Melmed on LinkedIn: linkedin.com/in/max-melmedThe Augment Exchange: augment.market/exchangeAugment: augment.marketABOUT THE SHOWThe Augment Exchange is a biweekly conversation about how private markets operate, with the people running it. Produced by Augment (augment.market), building the access and execution layer for the pre-IPO market. New episodes every other Wednesday.DISCLAIMERPlease note that this conversation is for informational purposes only. None of the information provided represents investment advice, an offer, or the solicitation of an offer to buy or sell any security. The views expressed by guests in this video are their own and do not necessarily represent the views of Augment. All views are subject to change.Investing in private securities is speculative, illiquid, and involves substantial risk, including the potential loss of principal. Not all private companies will go public or have a liquidity event. “Pre-IPO” is used generally to describe a privately held company that may be viewed as a potential candidate for a future public offering. The term does not mean that the company has filed for, scheduled, or committed to an IPO. An IPO or other liquidity event may never occur.Augment Markets Inc. is a technology company. Brokerage services are offered through Augment Capital LLC, member FINRA/SIPC. Investment advisory services are offered through Augment Advisors LLC, an SEC-registered investment adviser. Augment Capital LLC and Augment Advisors LLC are wholly owned subsidiaries of Augment Markets Inc.Augment Markets and/or its affiliates, employees, or clients may hold positions in securities or other financial instruments mentioned in this communication. These positions may change at any time without notice.Nothing contained herein should be construed as investment, legal, or tax advice, or as a recommendation to buy, sell, or hold any security. Recipients should conduct their own due diligence and consult their own professional advisors before making any investment decisions.Please see Augment’s disclosures here: https://augment.market/disclosures

Adam Bergman had a master's in tax law and no idea an IRA could own alternative assets. Then a client asked to put IRA money into a hedge fund, and the answer blew him away: the code never says what a retirement account can buy, only what it can't. He left Big Law and built IRA Financial on that fact. The retirement episode: the structures that move retirement money into alternatives, and the pitfalls at each step.In this episode, Max sits down with Adam Bergman, founder of IRA Financial. They discuss:• The Lyme story: why the cookie-cutter route does not fit everyone, in medicine or money• Three structures: self-directed IRA, checkbook LLC, solo 401k, and who each is for• The contribution gap: $7,500 in an IRA vs $72,000 in a solo 401k, and the UBIT trap• Backdoor Roths: the 2010 rule change, the pro rata wrinkle, and in-kind conversions• Peter Thiel's Roth: PayPal founders shares, and the case for going illiquid in an IRA• Alts in 401ks: the executive order, DOL safe harbors, and why litigation kept them outABOUT THE GUESTAdam Bergman is the founder of IRA Financial. A former tax and ERISA attorney at White & Case, Dewey & LeBoeuf, and Thelen, he found the space in 2008 when a client wanted a hedge fund in his IRA, and launched IRA Financial in 2010. The firm reports more than 27,000 clients and over $8 billion in assets. He has written nine books on self-directed retirement investing.LinkedIn: https://www.linkedin.com/in/adambergman1 Company: irafinancial.comMENTIONED IN THIS EPISODEPeter Thiel. PayPal. Bitcoin. Vanguard. Schwab. Fidelity. SpaceX. Anthropic. OpenAI. Trump accounts.FOLLOWMax Melmed on LinkedIn: linkedin.com/in/max-melmedThe Augment Exchange: augment.market/exchangeAugment: augment.marketABOUT THE SHOWThe Augment Exchange is a biweekly conversation about how private markets operate, with the people running it. Produced by Augment (augment.market), building the access and execution layer for the pre-IPO market. New episodes every other Wednesday.DISCLAIMERPlease note that this conversation is for informational purposes only. None of the information provided represents investment advice, an offer, or the solicitation of an offer to buy or sell any security. The views expressed by guests in this video are their own and do not necessarily represent the views of Augment. All views are subject to change.Investing in private securities is speculative, illiquid, and involves substantial risk, including the potential loss of principal. Not all private companies will go public or have a liquidity event. “Pre-IPO” is used generally to describe a privately held company that may be viewed as a potential candidate for a future public offering. The term does not mean that the company has filed for, scheduled, or committed to an IPO. An IPO or other liquidity event may never occur.Augment Markets Inc. is a technology company. Brokerage services are offered through Augment Capital LLC, member FINRA/SIPC. Investment advisory services are offered through Augment Advisors LLC, an SEC-registered investment adviser. Augment Capital LLC and Augment Advisors LLC are wholly owned subsidiaries of Augment Markets Inc.Augment Markets and/or its affiliates, employees, or clients may hold positions in securities or other financial instruments mentioned in this communication. These positions may change at any time without notice.Nothing contained herein should be construed as investment, legal, or tax advice, or as a recommendation to buy, sell, or hold any security. Recipients should conduct their own due diligence and consult their own professional advisors before making any investment decisions.Please see Augment’s disclosures here: https://augment.market/disclosures

The better Andrew Ryan's team got at their job, the less money they made. He has spent 25 years in venture services, where two-week deliveries and a broken process were simply assumed. He kept fixing it anyway. The venture services episode: how shares move from funds into LPs' hands, and what rebuilding capital formation would take.In this episode, Max sits down with Andrew Ryan, Managing Director of the Venture Capital Services Group at Alex. Brown, a division of Raymond James. They discuss:• Distributions in kind: SpaceX's rolling lockup, SPVs vs. VC discretion, and why the IPO isn't your event• The two-week myth: physical certificates, Hurricane Sandy, and same-day delivery• A business done for free: trading net, the case for fees, and the problem with indirect pay• Lockups, SPACs, and direct listings: what each solved and what each missed• The rebuild: a capital formation ladder, connected ATSs, and markets as a geopolitical assetABOUT THE GUESTAndrew Ryan is a Managing Director at Alex. Brown, a division of Raymond James, leading its Venture Capital Services Group. He started at Robertson Stephens in 2001, spent eight years at Jefferies, ran Deutsche Bank's venture capital services team, and joined Alex. Brown in 2016.LinkedIn: https://www.linkedin.com/in/andrewlryanabvcs/Company: alexbrown.comOUTLINE(00:00) What venture services actually does (11:35) Certificates and Hurricane Sandy (13:44) SpaceX lockups and distributions in kind (21:19) Delivery instructions, same-day stock (26:52) An eight-year sales cycle (32:58) Fixing inefficiencies, not exploiting (39:03) Lockups, SPACs, and direct listings (48:52) The right wrapper for private markets (58:53) A geopolitical asset (1:11:20) Advice for the newly liquid (1:23:25) Legacy: changing Wall Street MENTIONED IN THIS EPISODEAlex. Brown. Raymond James. Robertson Stephens. Jefferies. SpaceX. Uber. Fidelity. Anthropic.FOLLOWMax Melmed on LinkedIn: linkedin.com/in/max-melmedThe Augment Exchange: augment.market/exchangeAugment: augment.marketABOUT THE SHOWThe Augment Exchange is a biweekly conversation about how private markets operate, with the people running it. Produced by Augment (augment.market), building the access and execution layer for the pre-IPO market. New episodes every other Wednesday.DISCLAIMERPlease note that this conversation is for informational purposes only. None of the information provided represents investment advice, an offer, or the solicitation of an offer to buy or sell any security. The views expressed by guests in this video are their own and do not necessarily represent the views of Augment. All views are subject to change.Investing in private securities is speculative, illiquid, and involves substantial risk, including the potential loss of principal. Not all private companies will go public or have a liquidity event. “Pre-IPO” is used generally to describe a privately held company that may be viewed as a potential candidate for a future public offering. The term does not mean that the company has filed for, scheduled, or committed to an IPO. An IPO or other liquidity event may never occur.Brokerage services are offered through Augment Capital LLC, member FINRA and SIPC. Investment advisory services are offered through Augment Advisors LLC, an SEC-registered investment adviser. Both are wholly-owned subsidiaries of Augment Markets Inc.Augment Markets and/or its affiliates, employees, or clients may hold positions in securities or other financial instruments mentioned in this communication. These positions may change at any time without notice.Nothing contained herein should be construed as investment, legal, or tax advice, or as a recommendation to buy, sell, or hold any security. Recipients should conduct their own due diligence and consult their own professional advisors before making any investment decisions.Please see Augment’s disclosures here: https://augment.market/disclosures

Jeremy Neilson was pushing his child on a swing when AngelList called. The ask, in an Australian accent: can you do funds in bulk? He said yes, and the yes became Assure, the firm that ran over 9,000 SPVs before the great re-pricing of 2022 that halted SPV volume took down the firm. The SPV episode: where the structure came from, what took Assure down, and why Jeremy came back to build Sally.In this episode, Max sits down with Jeremy Neilson, founder and CEO of Sally. They discuss:- The origin: eight SPVs from AngelList, no website, no marketing, and a phone that would not stop ringing- From $300,000 and six months to a few days and $8,000: the cost collapse that made SPVs mainstream- The whipsaw: 50 employees to 215 to zero, and layoffs chasing a bottom Assure could not catch- Four SPVs, over $400 million, 48 hours: the deal that proved what the vehicle could do- Sally's bet: pure software, white label, recurring revenue, and every feature in code- SPV secondaries: investors trading seats with or without permission, and pre-IPO liquidityABOUT THE GUESTJeremy Neilson is the founder and CEO of Sally, a white-labeled software platform that automates launching and administering SPVs. He ran the State of Utah's $300 million fund of funds for seven years, then co-founded Assure in 2012 and built it into one of the largest SPV administrators before shutting it down in late 2022. Sally is his return to the market he helped create.LinkedIn: https://www.linkedin.com/in/jeremyneilson Company: sally.coOUTLINE(00:00) The AngelList cold call(02:14) What is an SPV(04:08) Eight SPVs to 9,000(09:24) SPVs will eat the world(16:08) The boom: 50 to 215 employees(18:15) Chasing a bottom they could not catch(21:10) Shutting down Assure(28:17) Sally, the fifth iteration(34:43) Four SPVs, $400M, 48 hours(39:26) Software, not services(47:05) SPVs as the liquidity layer(54:04) Why Jeremy said yesMENTIONED IN THIS EPISODEAngelList. Assure. Sally. CapLight. Forge. EquityZen. CartaX. Utah Fund of Funds.FOLLOWMax Melmed on LinkedIn: linkedin.com/in/max-melmedThe Augment Exchange: augment.market/exchangeAugment: augment.marketABOUT THE SHOWThe Augment Exchange is a biweekly conversation about how private markets operate, with the people running it. Produced by Augment (augment.market), building the access and execution layer for the pre-IPO market. New episodes every other Wednesday.DISCLAIMERPlease note that this conversation is for informational purposes only. None of the information provided represents investment advice, an offer, or the solicitation of an offer to buy or sell any security. All views are subject to change.Investing in private securities is speculative, illiquid, and involves substantial risk, including the potential loss of principal. Not all private companies will go public or have a liquidity event. “Pre-IPO” is used generally to describe a privately held company that may be viewed as a potential candidate for a future public offering. The term does not mean that the company has filed for, scheduled, or committed to an IPO. An IPO or other liquidity event may never occur.Brokerage services are offered through Augment Capital LLC, member FINRA and SIPC. Investment advisory services are offered through Augment Advisors LLC, an SEC-registered investment adviser. Both are wholly-owned subsidiaries of Augment Markets Inc.Augment Markets and/or its affiliates, employees, or clients may hold positions in securities or other financial instruments mentioned in this communication. These positions may change at any time without notice.Nothing contained herein should be construed as investment, legal, or tax advice, or as a recommendation to buy, sell, or hold any security. Recipients should conduct their own due diligence and consult their own professional advisors before making any investment decisions.Please see Augment’s disclosures here: https://augment.market/disclosures

Walter Chen worked the Lehman Brothers bankruptcy as a lawyer. Then he quit. He built and sold iDoneThis, bootstrapped Animalz to eight figures with clients like Zapier and Airtable, then started Sacra to cover the pre-IPO market. The research episode: how Sacra covers private companies, and how investors use research in a market with limited information.In this episode, Max sits down with Walter Chen, co-founder and CEO of Sacra. They discuss:• Content marketing after SEO: the B2B SaaS playbook, AI-generated content, and the site that 100x'd traffic then lost 99 percent• Coverage strategy: why Sacra goes deep on a few hundred companies while PitchBook tracks millions• How Sacra does research: web scraping, expert interviews, an AI voice agent, and the Sacra MCP• Why Sacra does not make buy or sell recommendations, and how AI tools personalize the research instead• Diligence on secondaries: evaluating deals without the information rights of a traditional data room• The dating app problem: Reddit's pre-IPO traffic spike, churn after the IPO, and building through the next cycleEpisode Outline(00:00) Intro (01:21) From Lehman lawyer to bootstrapped founder (04:01) SEO is dead: content in the AI era (09:35) 600 companies deep, not 3 million wide (11:55) The Carta conversation that seeded Sacra (15:54) The ecosystem mission and founder access (20:43) No buy or sell calls: how Sacra adds value (22:54) Diligence without a data room (25:03) Consolidation and staying independent (28:34) Churn after the IPO and the SpaceX problem (31:02) What's next: defense, robotics, physical AI (36:24) Moats when the model companies move in (40:28) Ramp's data as an economic signal(42:08) Magic wand: one view across every deal(43:59) Private markets in five yearsABOUT THE GUESTWalter Chen is the co-founder and CEO of Sacra. He started as a lawyer at Jenner & Block, then co-founded iDoneThis, a team productivity tool acquired in 2015. He founded Animalz, a content marketing agency whose clients included Zapier, Amplitude, and Airtable, and co-founded Sacra with Jan-Erik Asplund in 2020. Sacra's research now sits inside the workflows of the platforms and funds moving the pre-IPO market.LinkedIn: https://www.linkedin.com/in/whchen Company: sacra.comMENTIONED IN THIS EPISODELehman Brothers. Carta. Zapier. Airtable. Amplitude. PitchBook. Ramp. Deel. Reddit. OpenAI. Anthropic. SpaceX. Anduril. The Power 20: https://augment.market/the-power-20FOLLOWMax Melmed on LinkedIn: linkedin.com/in/max-melmedThe Augment Exchange: augment.market/exchangeAugment: augment.marketABOUT THE SHOWThe Augment Exchange is a biweekly conversation about how private markets operate, with the people running it. Produced by Augment (augment.market), building the access and execution layer for the pre-IPO market. New episodes every other Wednesday.DISCLAIMERPlease note that this conversation is for informational purposes only. None of the information provided represents investment advice, an offer, or the solicitation of an offer to buy or sell any security. All views are subject to change. Investing in private securities is speculative, illiquid, and involves substantial risk, including the potential loss of principal. Not all private companies will go public or have a liquidity event. “Pre-IPO” is used generally to describe a privately held company that may be viewed as a potential candidate for a future public offering. The term does not mean that the company has filed for, scheduled, or committed to an IPO. An IPO or other liquidity event may never occur. Brokerage services are offered through Augment Capital LLC, member FINRA and SIPC. Investment advisory services are offered through Augment Advisors LLC, an SEC-registered investment adviser. Both are wholly-owned subsidiaries of Augment Markets Inc. Augment Markets and/or its affiliates, employees, or clients may hold positions in securities or other financial instruments mentioned in this communication. These positions may change at any time without notice. Nothing contained herein should be construed as investment, legal, or tax advice, or as a recommendation to buy, sell, or hold any security. Recipients should conduct their own due diligence and consult their own professional advisors before making any investment decisions. Please see Augment’s disclosures here: https://augment.market/disclosures