Description
Join the Lossdog waitlist at https://lossdog.com and please subscribe to this channel.
Tom Sosnoff and Scott Sheridan kick off December with a deep dive into startup investing and raising capital, drawing from their decades of experience building thinkorswim and tastytrade. The episode tackles whether borrowing against home equity for a startup makes sense, key dos and donts for job interviews, and why you should always maximize your 401k match. Tom delivers a pointed rant against tech billionaires advising young people to skip college while hiring exclusively from elite universities. The show closes with market analysis covering bonds, digital assets, and why silver looks overcooked at current levels.
#startups #investing #entrepreneurship #career #salarynegotiation #stockmarket
TIMESTAMPS
0:00 Intro
1:19 Happy Monday and Bears football recap
6:34 Peking turkey Thanksgiving review
13:58 New show time announcement 7 PM ET
15:40 Mailbag: Should you take a home equity loan for a startup
19:00 Job interview dos and donts
24:17 Why you must maximize 401k matching
25:32 Raising capital vs building your product first
30:42 Venture capital vs private equity explained
35:12 Investing in a startup: Key rules
41:28 When investing in a startup is a bad idea
48:29 Assessing startup risk: Team market product and financial
56:16 Anti-college advice rant: Why tech bros are wrong
59:45 Words of wisdom: Raising capital methods
1:07:05 Lossdog software preview and features
1:13:30 Market talk: Bonds digital assets and stock picks
College remains one of the few institutions offering social mobility for people without wealthy parents, yet billionaire tech founders who attended Stanford and Harvard keep telling young people to skip it. With student debt at record levels and AI threatening entry-level jobs, the debate over higher education ROI has never been more heated. Meanwhile, startup founders face brutal fundraising environments where 97-99% of ventures fail, making the decision to bootstrap versus seek venture capital more consequential than ever. This episode provides practical frameworks for both investing in startups and raising capital, drawing from real experience building multiple successful companies through market crashes.
ABOUT ONE LUCKY DOG / LOSSDOG
One Lucky Dog is your daily wake-up call for career and financial clarity—streaming live Monday through Thursday, 10-11am ET. Hosts Tom Sosnoff and Scott Sheridan (the founders behind thinkorswim and tastytrade) along with co-host Sol bring decades of experience democratizing finance, now turning their attention to something just as broken: how we understand our professional worth.
Lossdog is the platform they're building to fix it. It's AI-powered software that doesn't just guess what you should earn—it calculates your real market value and shows you exactly how to increase it. No more vague salary ranges. No more wondering if you're being underpaid. Just clarity, backed by data.
The show is the conversation. The platform is the tool. Together, they're designed to help you stop leaving money on the table and start building the career you actually deserve.
📺 Watch live: Mon-Thu 10-11am ET
📞 Call in: 989-LOSSDOG
📧 oneluckydog@lossdog.com
🐕 Follow @wearelossdog everywhere 👉 http://linktr.ee/wearelossdog
Everyone has a number. Lossdog helps you find yours—and grow it.
👉 Join the waitlist at https://lossdog.com/
Tom Sosnoff and Scott Sheridan kick off December with a deep dive into startup investing and raising capital, drawing from their decades of experience building thinkorswim and tastytrade. The episode tackles whether borrowing against home equity for a startup makes sense, key dos and donts for job interviews, and why you should always maximize your 401k match. Tom delivers a pointed rant against tech billionaires advising young people to skip college while hiring exclusively from elite universities. The show closes with market analysis covering bonds, digital assets, and why silver looks overcooked at current levels.
#startups #investing #entrepreneurship #career #salarynegotiation #stockmarket
TIMESTAMPS
0:00 Intro
1:19 Happy Monday and Bears football recap
6:34 Peking turkey Thanksgiving review
13:58 New show time announcement 7 PM ET
15:40 Mailbag: Should you take a home equity loan for a startup
19:00 Job interview dos and donts
24:17 Why you must maximize 401k matching
25:32 Raising capital vs building your product first
30:42 Venture capital vs private equity explained
35:12 Investing in a startup: Key rules
41:28 When investing in a startup is a bad idea
48:29 Assessing startup risk: Team market product and financial
56:16 Anti-college advice rant: Why tech bros are wrong
59:45 Words of wisdom: Raising capital methods
1:07:05 Lossdog software preview and features
1:13:30 Market talk: Bonds digital assets and stock picks
College remains one of the few institutions offering social mobility for people without wealthy parents, yet billionaire tech founders who attended Stanford and Harvard keep telling young people to skip it. With student debt at record levels and AI threatening entry-level jobs, the debate over higher education ROI has never been more heated. Meanwhile, startup founders face brutal fundraising environments where 97-99% of ventures fail, making the decision to bootstrap versus seek venture capital more consequential than ever. This episode provides practical frameworks for both investing in startups and raising capital, drawing from real experience building multiple successful companies through market crashes.
ABOUT ONE LUCKY DOG / LOSSDOG
One Lucky Dog is your daily wake-up call for career and financial clarity—streaming live Monday through Thursday, 10-11am ET. Hosts Tom Sosnoff and Scott Sheridan (the founders behind thinkorswim and tastytrade) along with co-host Sol bring decades of experience democratizing finance, now turning their attention to something just as broken: how we understand our professional worth.
Lossdog is the platform they're building to fix it. It's AI-powered software that doesn't just guess what you should earn—it calculates your real market value and shows you exactly how to increase it. No more vague salary ranges. No more wondering if you're being underpaid. Just clarity, backed by data.
The show is the conversation. The platform is the tool. Together, they're designed to help you stop leaving money on the table and start building the career you actually deserve.
📺 Watch live: Mon-Thu 10-11am ET
📞 Call in: 989-LOSSDOG
📧 oneluckydog@lossdog.com
🐕 Follow @wearelossdog everywhere 👉 http://linktr.ee/wearelossdog
Everyone has a number. Lossdog helps you find yours—and grow it.
👉 Join the waitlist at https://lossdog.com/
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