From $15M to $850M: The Trading System Behind It (ft. Ross Haber)

From $15M to $850M: The Trading System Behind It (ft. Ross Haber)

30 views · September 13th, 2026

Ross Haber helped grow a fund from $15 million to $850 million alongside legendary investor William O'Neill. He breaks down the system behind it, and the hard-won lessons that actually separate winning traders from everyone else. He joins Gav to walk through his approach on live charts: how he modernized the CAN SLIM method into his "launch pad" setup, why he stopped chasing breakouts and started buying earlier, why managing risk matters far more than picking the right stock, and how he reads the current market (including memory, semis, and where he sees leadership forming). Subscribe to our FREE Newsletter: https://marketmadness-newsletter.beehiiv.com/ ▶ Follow Ross Haber: X: @RossHaber Trader Lion: traderlion.com ▶ Follow WOLF Financial: X: https://x.com/WOLF_Financial X: https://x.com/TheETFTracker This content is for informational purposes only and does not constitute investment advice. The views expressed by guests are their own and do not necessarily reflect those of WOLF Financial. Any track records or results discussed are historical and are not indicative of future results. Investing involves risk, including the possible loss of principal. 00:00 Intro 00:36 From O'Neill broker to running an $850M fund 03:45 What he was buying in 1999 (and why 2026 feels like 1996) 08:13 The launch pad setup: modernizing CAN SLIM 11:52 Why he now buys earlier instead of chasing breakouts 16:22 Why picking stocks is the easy part 17:16 The real reason 90% of traders lose 20:00 Reading the charts: memory, semis, and late-stage bases 28:15 His read on the current market

Phong Le: We Hold 4% Of The Bitcoin In The World

3 views · September 11th, 2026

Phong Le describes the weight that comes with the position his company occupies, roughly $66 billion in capital and, by his account, four percent of all Bitcoin. As Bitcoin becomes more systemically important, he argues, so does the company holding that much of it. That's the reasoning behind the openness: hundreds of millions of people are exposed to the securities, and many have put retirement money and net worth into them. In his view anyone taking that risk should get transparency into leadership and strategy in both good times and bad. Watch the full episode powered by WOLF Financial: https://youtu.be/UEIZD7_JWG8?si=7UD9vkIqP5D9BN8s

Strategy CEO: Inside the World's Biggest Bitcoin Bet (ft. Phong Le)

37 views · September 11th, 2026

Strategy has become the largest corporate holder of Bitcoin on the planet, holding roughly 4% of all the Bitcoin that will ever exist. CEO Phong Le explains the thinking behind the boldest treasury strategy in public markets. He joins the show to break down why he believes Bitcoin is a non-sovereign store of value, what it means to be "amplified Bitcoin," how he thinks about inflation and the debasement of the dollar, and the long-term vision for giving more people access to Bitcoin through the public markets. Subscribe to our FREE Newsletter: https://marketmadness-newsletter.beehiiv.com/ ▶ Follow WOLF Financial: X: https://x.com/WOLF_Financial X: https://x.com/TheETFTracker This content is for informational and educational purposes only and is not investment advice. The guest is the CEO of Strategy (MSTR) and discusses the company and its Bitcoin-related securities; his views reflect his own interests and do not necessarily reflect those of WOLF Financial. Bitcoin and leveraged Bitcoin-linked securities are highly volatile and speculative, and you could lose your entire investment. Nothing here is a recommendation to buy or sell any asset or security. Past performance is not indicative of future results. 00:00 Intro: the world's largest corporate Bitcoin holder 01:30 What "amplified Bitcoin" actually means 02:52 Why Bitcoin as a non-sovereign store of value 05:22 The burrito test: understanding real inflation 07:18 Lessons from Argentina and Vietnam 10:00 How Strategy gives access to Bitcoin through markets 14:00 The long-term vision 20:00 Volatility, conviction, and the road ahead

Brian Feroldi: Why Big Stocks Are More Likely to 10x Than Small Ones

32 views · September 8th, 2026

Every investor is taught that small stocks have more room to run. Brian Feroldi came across data that flipped that belief on its head, and it changed how he invests. He joins Gav to break down the study that "broke his brain" (why a $100 billion company is far more likely to become a trillion-dollar company than a small cap is to 10x), what it means for how you build a portfolio, and the counterintuitive rule he follows when trimming: cull your losers, feed your winners. Subscribe to our FREE Newsletter: https://marketmadness-newsletter.beehiiv.com/ ▶ Follow Brian Feroldi: X: https://x.com/BrianFeroldi YouTube: @BrianFeroldi ▶ Follow WOLF Financial: X: https://x.com/WOLF_Financial X: https://x.com/TheETFTracker This content is for informational purposes only and does not constitute investment advice. The views expressed by guests are their own and do not necessarily reflect those of WOLF Financial. Investing involves risk, including the possible loss of principal. Past performance is not indicative of future results.

The IT Guy Said No And It Made Him A Fortune

52 views · September 7th, 2026

In 2006 Gary Vaughan of Daily Stock Picks asked his new employer's IT department for an iPhone and got turned down. Then he asked a follow up question: how many new hires had asked for the same thing. The answer was every single one of them, all 40 that day. He took his $10,000 signing bonus and bought Apple stock instead of waiting for the company to catch up. He still holds it. Watch the full episode powered by WOLF Financial: https://youtu.be/4DkGmI98MI4?si=18koQ7cvBK2sGv1s This content is for informational and entertainment purposes only and is not investment advice. Nothing presented constitutes a recommendation to buy or sell any security. Always do your own research.

Why the Smartest Founders Are Moving Into Robotics (ft. Robinhood Ventures Fund)

36 views · September 7th, 2026

The best early-stage founders are shifting from software to the physical world, and robotics is where a growing share of them are heading. The team behind Robinhood Ventures Fund II explains why the next frontier is moving AI off the screen and into the real world. Sarah Pinto and Rich Aberman join Gav to talk through the themes they're most excited about in early-stage investing, why robotics (both humanoid and application-specific) may be the next big leap, how AI is reshaping healthcare, and why they encourage investors to actually research the companies behind the fund. ▶ Follow Robinhood Ventures: X: @RobinhoodApp robinhood.com/ventures ▶ Follow WOLF Financial: X: https://x.com/WOLF_Financial X: https://x.com/TheETFTracker This content is for informational purposes only and is not investment advice. The guests are affiliated with Robinhood and the fund discussed. Investing in early-stage and private companies is highly speculative and illiquid; most early-stage companies fail, and you could lose your entire investment. Closed-end funds may trade at a premium or discount to net asset value. Read the prospectus before investing. Past performance is not indicative of future results.

The Signing Bonus That Became a Fortune (ft. Gary Vaughan, Daily Stock Picks)

5 views · September 5th, 2026

In 2006, Gary Vaughan noticed something simple at his new job: every single new hire wanted an iPhone. So he took his $10,000 signing bonus, put it all into Apple, and never sold. Today that position is worth millions. He joins Gav to break down the buy-and-hold philosophy behind it, why compounding beats constant trading, how he thinks about trimming winners versus letting them ride, and where he still sees long-term opportunity across the Mag 7, AMD, and memory. Subscribe to our FREE Newsletter: https://marketmadness-newsletter.beehiiv.com/ ▶ Follow Gary Vaughan / Daily Stock Picks: X: @dailystockpick3 ▶ Follow WOLF Financial: X: https://x.com/WOLF_Financial X: https://x.com/TheETFTracker This content is for informational purposes only and does not constitute investment advice. Any results discussed reflect the guest's own historical experience and are not typical, not guaranteed, and not indicative of future results. The views expressed are the guest's own and do not necessarily reflect those of WOLF Financial. Investing involves risk, including the possible loss of principal.

Eric Trump: The Hard Asset Guy Who Ended Up In Bitcoin

40 views · September 4th, 2026

Eric Trump spent his career in steel, drywall and concrete, the kind of assets you can walk through and touch, and says he never expected to end up advocating for something most people file as intangible. What changed it was seeing the physical side of mining up close through American Bitcoin, the 90,000 servers, the energy running through them, the real cost of securing the network. He now calls Bitcoin a compliment to hard physical assets rather than a departure from them. Watch the full episode powered by WOLF Financial: https://youtu.be/HK-rKM2NiZk This content is for informational and entertainment purposes only and is not investment advice. Nothing presented constitutes a recommendation to buy or sell any security. Always do your own research.

How He Turned $10K Into Millions in the Stock Market (ft. Gary Vaughan, Daily Stock Picks)

23 views · September 3rd, 2026

In 2006, Gary Vaughan put a $10,000 signing bonus into a single stock and never sold. Today that position is worth millions. He shares the simple decision behind it and the buy-and-hold philosophy that built his wealth. He joins Gav to explain why patience and compounding beat constant trading, the Apple bet that started before he even understood investing, the mistakes he regrets most (trimming winners, trading in and out of Google), and how he thinks about risk at 56 versus what he'd tell someone in their 20s. Subscribe to our FREE Newsletter: https://marketmadness-newsletter.beehiiv.com/ ▶ Follow Daily Stock Picks: X: @dailystockpick3 YT: https://www.youtube.com/@UCTunv_39Cff5FIGVGI3eqbw ▶ Follow WOLF Financial: X: https://x.com/WOLF_Financial X: https://x.com/TheETFTracker This content is for informational purposes only and does not constitute investment advice. The views expressed by guests are their own and do not necessarily reflect those of WOLF Financial. Any results or performance discussed are the guest's own historical experience and are not indicative of future results. Investing involves risk, including the possible loss of principal. 00:00 Intro 02:05 Why he trades far less than people think 03:00 The regret trades: trimming Apple, trading Google, missing Tesla 06:44 Why "buy and hold" beats chasing 07:50 The $10,000 Apple bet that became millions 12:09 The other long-term holds he believes in 16:00 Following Jensen's cue into memory (and the Micron call) 20:28 Rinse and repeat: finding a strategy that works 29:50 Why time and compounding are your best friend

Eric Trump: Name Anything Digitized That Hasn't Won

23 views · September 2nd, 2026

Eric Trump describes an approach built on conviction rather than precision, adding to positions on deep drawdowns while accepting that nobody catches the exact bottom. His reasoning rests on a pattern he says has never broken: name a technology that got digitized and then lost the long term race. Photography went from eight millimeter film to live streaming. The telephone went the same way. He argues Swift and traditional banking are the next in line, because something faster, cheaper and more transparent tends to win. Watch the full episode powered by WOLF Financial: https://youtu.be/HK-rKM2NiZk?si=9heScUu0SZBmGBoX This content is for informational and entertainment purposes only and is not investment advice. Nothing presented constitutes a recommendation to buy or sell any security. Always do your own research.

Eric Trump: Why a Real Estate Guy Believes in Bitcoin

71 views · September 1st, 2026

Eric Trump built his career on hard assets, steel, concrete, real estate. So how did he become one of Bitcoin's most vocal believers? He explains the conviction behind why he says he'll "ride Bitcoin forever." He joins Gav to share how his family's debanking experience pulled him into crypto, why he believes digital always beats analog over time, how he compares Bitcoin to real estate as a store of value, and why he says it takes real "spine" to hold through the volatility. Note: Eric Trump is co-founder of American Bitcoin, a Bitcoin mining company, and discusses Bitcoin throughout. See the full disclosure below. Subscribe to our FREE Newsletter: https://marketmadness-newsletter.beehiiv.com/ ▶ Follow Eric Trump: X: @EricTrump ▶ Follow WOLF Financial: X: https://x.com/WOLF_Financial X: https://x.com/TheETFTracker This content is for informational and educational purposes only and is not investment advice. The guest has financial interests in Bitcoin and in companies discussed in this video, including American Bitcoin. His views are his own and do not necessarily reflect those of WOLF Financial. Cryptocurrency is highly volatile and speculative, and you could lose your entire investment. Past performance is not indicative of future results.

Eric Trump: Why the Banks Won't Survive This

436 views · August 31st, 2026

Eric Trump thinks the traditional banking system is on borrowed time. In this conversation, he lays out why he believes the biggest banks either adapt to crypto or become obsolete. He joins Gav to explain why firms like Fidelity and Schwab are already building digital-asset wallets into everyday accounts, his vision for a world where almost anything can be tokenized, from music to real estate, and why he believes this shift is happening faster than most people realize. Note: Eric Trump is co-founder of American Bitcoin and is affiliated with World Liberty Financial (USD1), which he discusses in this video. See the full disclosure below. Subscribe to our FREE Newsletter: https://marketmadness-newsletter.beehiiv.com/ ▶ Follow Eric Trump: X: @EricTrump ▶ Follow WOLF Financial: X: https://x.com/WOLF_Financial X: https://x.com/TheETFTracker This content is for informational and educational purposes only and is not investment advice. The guest has financial interests in Bitcoin and in companies and products discussed in this video, including American Bitcoin and World Liberty Financial (USD1). His views are his own and do not necessarily reflect those of WOLF Financial. Cryptocurrency is highly volatile and speculative, and you could lose your entire investment. Past performance is not indicative of future results. 00:00 Will the big banks adapt to crypto? 00:45 Why Eric thinks banks become extinct without it 01:26 Fidelity and Schwab already building it in 01:46 The tokenization of everything: music, art, real estate 03:00 World Liberty, stablecoins, and the rails of finance 04:11 His advice: open an account and actually try it 05:22 Why crypto takes "backbone" to hold

Eric Trump: Why America Needs Crypto Clarity (Full Interview)

4 views · August 28th, 2026

Eric Trump went from running a real estate empire to becoming one of crypto's most visible believers. In this conversation, he makes his case for why the US should lead the world in Bitcoin and digital assets. He joins Gav to explain how his family's debanking experience pulled him into crypto, why he views Bitcoin as a hard asset with staying power, how he thinks about volatility and conviction, and why he believes America's energy advantage positions it to lead in both crypto and AI. Note: Eric Trump is co-founder of American Bitcoin and is affiliated with World Liberty Financial (USD1). He discusses Bitcoin and these ventures throughout. See the full disclosure below. Subscribe to our FREE Newsletter: https://marketmadness-newsletter.beehiiv.com/ ▶ Follow Eric Trump: X: @EricTrump ▶ Follow WOLF Financial: X: https://x.com/WOLF_Financial X: https://x.com/TheETFTracker This content is for informational and educational purposes only and is not investment advice. The guest has financial interests in Bitcoin and in companies and products discussed in this video, including American Bitcoin and World Liberty Financial (USD1). His views are his own and do not necessarily reflect those of WOLF Financial. Cryptocurrency is highly volatile and speculative, and you could lose your entire investment. Nothing here is a recommendation to buy or sell any asset. Past performance is not indicative of future results. 00:00 Intro 00:40 How debanking pulled his family into crypto 02:56 Why volatility requires "spine" to hold Bitcoin 03:38 His buying strategy: conviction and buying dips 06:11 Bitcoin vs real estate: liquidity and hard assets 11:57 Why he thinks the US must lead the crypto race 15:34 Power as the real constraint for crypto and AI 30:00 Stablecoins, USD1, and the rails of modern finance 32:27 His advice: open an account and actually try it

You NEED to Watch This Before You Invest in the New Robinhood Venture Fund

13 views · August 27th, 2026

For most of history, investing in early-stage startups was reserved for the wealthy and well-connected. Robinhood Ventures is trying to change that, and there's a lot you should understand before you consider it. Sarah Pinto (Head of Robinhood Ventures) and Rich Aberman join Gav to explain how their new fund gives everyday investors access to a diversified portfolio of early-stage Y Combinator startups, how it differs from their later-stage fund, how the closed-end structure and daily liquidity actually work, and the real risks of investing in an asset class where most companies fail. Subscribe to our FREE Newsletter: https://marketmadness-newsletter.beehiiv.com/ ▶ Follow Robinhood Ventures: X: @RobinhoodApp robinhood.com/ventures ▶ Follow WOLF Financial: X: https://x.com/WOLF_Financial X: https://x.com/TheETFTracker This content is for informational purposes only and is not investment advice. The guests are affiliated with Robinhood and the fund discussed. Investing in early-stage and private companies is highly speculative and illiquid; most early-stage companies fail, and you could lose your entire investment. Closed-end funds may trade at a premium or discount to net asset value. Read the prospectus before investing. Past performance is not indicative of future results. 00:00 Intro: meet the Robinhood Ventures team 01:30 Why startups were off-limits to regular investors 03:00 RVI vs RVII: later-stage names vs early-stage bets 05:00 Why they built the early-stage fund around Y Combinator 09:00 What makes YC the best startup pipeline 13:00 How the closed-end fund structure works 16:00 NAV, premiums, discounts, and daily liquidity 20:00 The real risks of early-stage investing 24:00 Who this fund is (and isn't) built for

Matt Hougan: The Case For Bitcoin At $1.3 Million By 2035

6 views · August 26th, 2026

Matt Hougan strips the Bitcoin case down to one idea: it provides a service the world wants, the ability to store wealth digitally without a government or a bank, the same job gold does physically. If even a small fraction of the world decides it wants that, he sees enormous room left, with Bitwise modeling roughly $1.3 million a coin by 2035. He frames it against a backdrop most people have stopped registering, over $40 trillion in national debt and more money printed last quarter than during the financial crisis. Watch the full episode powered by WOLF Financial: https://youtu.be/GRIWcowlc-o?si=wPHLBFhNaNJpov4Y

Brian Feroldi: Why He Buys Stocks at All-Time Highs

10 views · August 25th, 2026

Everyone's taught to wait for a dip and never overpay. Brian Feroldi says some of the best investments of his life were bought at all-time highs, when nothing about them looked cheap. He joins Gav to explain why quality and growth matter far more than an optical bargain, why the P/E ratio misleads more investors than it helps, how to actually read a financial statement based on what phase a business is in, and the Amazon purchase at a 500 P/E that became one of his best buys ever. Subscribe to our FREE Newsletter: https://marketmadness-newsletter.beehiiv.com/ ▶ Follow Brian Feroldi: X: https://x.com/BrianFeroldi YouTube: @BrianFeroldi ▶ Follow WOLF Financial: X: https://x.com/WOLF_Financial X: https://x.com/TheETFTracker This content is for informational purposes only and does not constitute investment advice. The views expressed by guests are their own and do not necessarily reflect those of WOLF Financial. Investing involves risk, including the possible loss of principal. Past performance is not indicative of future results.