The Super Upside Factor with Daniel Kang
Lifeselfmastery's podcast I Startups I Venture Capital
Release Date: 03/27/2025
Ali Hafizji from Wednesday on MVP Mistakes and Finding Product-Market Fit
Lifeselfmastery's podcast I Startups I Venture Capital
is the CEO of , an engineering services company specializing in - Data Engineering, Generative AI, and Application Modernization. In this episode, Ali Hafizji, founder of Wednesday, shares how his frustration with clunky banking APIs sparked the idea to launch a high-performance engineering services firm. He dives into building outcome-focused teams, the evolution from MVP to product-market fit, and why founders must shift from intuition to data. Ali unpacks common mistakes startups make post-MVP, tips for leveraging AI tools effectively, and why retention—not vanity metrics—matters most....
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Building AI-Driven Teams, Scalable Services, and a Global Career with Tom Kelly of Braze
Lifeselfmastery's podcast I Startups I Venture Capital
I am thrilled to have , a global tech leader and angel investor, works as the senior director of account management at Braze. With deep expertise in customer success, AI adoption, and GTM strategy, Tom builds high-performing teams and invests in the next wave of startups shaping the future of tech. In this episode, Tom Kelly, Senior Director at Braze and angel investor, shares his journey from physics and hedge funds to building global technical account teams. Tom dives into launching a new services arm inside a high-growth SaaS company, how to scale AI adoption across teams, and why...
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How AI Can Fix Gen Z’s Financial Gaps with Jason Schappert from Moola
Lifeselfmastery's podcast I Startups I Venture Capital
I am thrilled to have Jason Schappert, the CEO of Moola, an AI-powered stock scoring and decision engine designed to empower the next generation of investors to achieve true financial freedom. Earlier - MzeroA was named one of the Inc. 500’s top-growing private companies and recognized as a “Best Place to Work.” In this episode, Jason Schappert, founder of Moola, shares his journey from pest control routes to an eight-figure exit. Jason dives into bootstrapping his aviation edtech startup, turning early YouTube lessons into a thriving business, and scaling with scrappy tools and mindset....
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Inside Supademo’s PLG Growth with Joseph Lee
Lifeselfmastery's podcast I Startups I Venture Capital
I am excited to have , the founder of Supademo - The fastest and easiest way to create high-converting interactive demos with AI. Over 70k professionals in marketing, growth, sales, and success use Supademo to enable customers, scale product adoption and close more deals. In this episode, Joseph Lee, founder of Supademo and former Freshline co-founder, shares his journey from seafood marketplaces to revolutionizing product demos. Joseph dives into building a product-led SaaS company, how Supademo scaled through SEO, Reddit, and handcrafted outreach, and why intuitive UX beats feature bloat. He...
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Vanessa Larco on the Future of Consumer Tech
Lifeselfmastery's podcast I Startups I Venture Capital
I am excited to have , who was a Partner at NEA and is now launching a fund called Premise, where she led investments in breakthrough companies like Cleo, Rocket.Chat, Mejuri, EvidentID, Greenlight Card, Feather, and Lily AI. She also served as a board observer for high-growth startups including Robinhood, Willow Pump, and OmniSci. In this episode, Vanessa Larco, ex-Partner at NEA and founding GP of Primis, shares her journey from product management at Microsoft and Box to becoming a leading early-stage VC. Vanessa dives into how AI is reshaping product roles, what makes the next wave of...
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The Sweaty Startup with Nick Huber
Lifeselfmastery's podcast I Startups I Venture Capital
I am thrilled to have , the founder of , a serial entrepreneur, investor, and popular content creator focused on small business ownership. Nick cofounded and operates his primary business, Bolt Storage, a commercial real estate firm, which owns 1.9 million square feet of self-storage facilities across 62 locations in 11 states. He is the author of the new book, The Sweaty Startup. In this episode, Nick Huber, founder of The Sweaty Startup and Bolt Storage, shares his journey from building a “boring” service business to managing 1.9 million square feet of self-storage facilities...
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Levi Velez Reed from Twig Ventures on Disrupting VC with Inclusivity and Conscious Capital
Lifeselfmastery's podcast I Startups I Venture Capital
Levi Velez Reed is the founder of Twig Ventures is an investment syndicate specialising in sustainable consumer products and tech startups across North America, targeting companies at the pre-seed to seed stage. In this episode, Levi Velez Reed, founder of Twig Ventures, shares his journey from bootstrapping a marketing agency in New York to launching an investment syndicate focused on sustainable consumer products and tech startups. He explains the impact of removing unconscious bias in VC funding, supporting underrepresented founders, and creating accessible accelerator programs like...
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Greg Alexander from Collective 54 on Building and Scaling Boutique Firms
Lifeselfmastery's podcast I Startups I Venture Capital
I am thrilled to have , the founder of , the first mastermind community for thriving professional services firms. Collective 54 helps founders and leaders grow, scale and exit their firms bigger and faster. In this episode, Greg Alexander, founder of Collective 54 and author of The Boutique, shares his journey of building and scaling professional services firms. He explains the three life-cycle stages: Grow, Scale, and Exit, and the importance of moving away from trading time for money. Greg discusses the unique business model of Collective 54, monetisation strategies for boutique firms,...
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How Renan Devillieres from OSS Ventures Is Reinventing Manufacturing with SaaS and AI
Lifeselfmastery's podcast I Startups I Venture Capital
Renan Devillieres is the CEO of OSS Ventures. Renan Devillieres is a CEO who is passionate about making a positive impact on society and the environment, and who believes in using technology to drive change. Renan has a wealth of experience in areas such as manufacturing operations, SaaS, and venture capital. Timestamps 01:00 – Renan’s unconventional path from Google search to joining McKinsey. 03:00 – Transition from factory director to building a tech startup; early failures and pivots. 05:10 – Moving to San Francisco, finding product-market fit, and exiting the company. 06:30...
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Shubham Khoker on Scaling Startups, Growth Lessons, and the Future of AI Agents
Lifeselfmastery's podcast I Startups I Venture Capital
was the Head of Growth at . Topmate.io is a fast-growing online platform that connects freelancers and clients, he used to lead the growth strategy and execution for the company. rifa.ai founder. IIT bombay In this episode, Shubham Khoker, former Head of Growth at Topmate and founder of Rifa AI, shares his unconventional journey from UPSC preparation to the startup world, insights from scaling Topmate in India and the US, lessons from failed experiments, and the evolution of the creator economy. He discusses the future of AI in growth and operations, the difference between growth sales and...
info_outlineDaniel Kang is the CEO & co-founder of Y-Combinator-backed startup Flowbo, a marketplace that provides financing to influencers and allows fans to share in their success. He is the author of his new book - The Super Upside Factor: Asymmetric Principles that Will 10x Your Life
In this episode, Daniel Kang, author of The Super Upside Factor, shares his journey from consulting at BCG to venture capital at SoftBank and ultimately founding Flowbo, a Y Combinator-backed marketplace that helps creators access capital. He discusses the challenges of building Flowbo during COVID-19, securing early customers, and the importance of asymmetric bets in life and business. Daniel also explains why writing led to his book The Super Upside Factor, how to think about quitting strategically, and why risk capital dynamics differ between the US and Europe, and much more!
Timestamps
00:02:30 – Daniel’s background
00:04:15 – Moving from consulting to venture capital
00:06:30 – Importance of building your own reputation rather than borrowing from prestigious companies.
00:10:20 – How Daniel identified the gap in financial access for freelancers and creators
00:12:10 – Challenges of raising funds during COVID-19.
00:14:50 – Early customer acquisition strategy and learning from Paul Graham’s "Do Things That Don’t Scale."
00:17:25 – Daniel's approach to connecting with creators by organizing exclusive events.
00:19:05 – Why writing became a powerful tool for Daniel to reflect on strategy and personal growth.
00:23:45 – Explanation of "asymmetric principles" and why VCs can afford to be wrong most of the time.
00:26:15 – Three key principles for asymmetric bets: Budget for failure, target high upsides, and use feedback loops.
00:28:40 – How these principles apply beyond investing to life and career decisions.
00:31:00 – Differences between US and European VC markets: Risk capital and founder dynamics.
00:34:45 – How AI is reshaping the startup ecosystem and reducing costs of launching companies.
00:37:15 – Why niche and distribution will matter more for future AI companies.
00:40:30 – Building a "life portfolio" and how Daniel manages risk in his personal and professional life.
00:43:20 – The correlation between household income and likelihood of pursuing creative careers.
00:45:55 – How asymmetric bets can help level the playing field for creatives from middle-class backgrounds.
00:49:00 – The art of quitting: Different types of quitting and when to walk away from a failing business.
00:52:10 – Why quitting isn’t necessarily a failure but a strategic decision.
00:54:45 – Advice for founders raising funds: Focus on creating value before raising money.
00:57:00 – Why founders should avoid private negotiations and aim for auction-like funding dynamics.
Daniel’s Links
LDN– https://www.linkedin.com/in/itsdankang/
Book - The Super Upside Factor: Asymmetric Principles that Will 10x Your Life
My Links
Podcast: https://lifeselfmastery.com/itunes
Newsletter: https://partner-grow.beehiiv.com/subscribe
YouTube: youtube.com/lifeselfmastery
Twitter: https://twitter.com/rohitmal
LinkedIn: https://www.linkedin.com/in/rohit857/
Agency: https://bit.ly/41YuNnx