The Undefeated Underdogs

Hosted by Sharath Kuruganty

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Feb 2025

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The Undefeated Underdogs is a podcast unpacking the underdog stories you never heard of! It highlights the underdog mentality and brings authentic conversations with people who play the long game, take action with a chip on their shoulders, and convert obstacles into opportunities! Buckle up, as I will be bringing some authentic founders, VCs, community builders, and content creators who got underestimated their whole life, and yet they beat the odds and became insanely successful!

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February 6, 2025Episode 7847 min

Andrew Yeung - How to build a million-dollar events company from scratch!

👉🏼 About the Guests: Business Insider dubbed Andrew Yeung as The Great Gatsby of startups. Andrew moved to the US as an immigrant in 2020 and after a brief stint at Facebook, Google he founded his events company Fibe, generated millions of dollars in revenue, hosted more than 40K tech folks, became a partner at Next Wave NYC, grew his personal brand - all this happened in the last 4yrs. 👉🏼 About the Host: Sharath is a founder, creator, and community builder. He is also a serial maker who built and shipped 15+ projects using no-code tools. His SaaS product Shoutout generated $30k ARR, which was sold to a UK-based product studio. Prev, Sharath worked for world-changing startups like Product Hunt and On Deck, where he helped build and nurture communities. He also grew his audience on Twitter from 200 to 24,000 using give-first principles and creating high-value content. He recently sold his second SaaS product, GuestLab, and he is working on a startup idea while hosting this show. 👉🏼 Sponsor Corner: Shoutout to Acquire.com for sponsoring The Undefeated Underdogs podcast! They’re the best online marketplace to buy/sell startups and I know many founders who have sold their businesses there. If you're looking to wind down your business and cash in some of your founder chips, check them out - https://try.acquire.com/sharath/ 👉🏼 Description: Listen in as Sharath and Andrew discuss networking, succeeding in America as underdogs, why NYC is awesome, and more! 👉🏼 Timestamps: 00:00: Episode Highlight 00:46: Shoutout to Acquire.com 03:14: Intro to Andrew Yeung - the Great Gatsby of startups 04:30: Why Andrew chose NYC and events over San Francisco and product-building 09:00: How Andrew entered tech 10:47: How Andrew built his network in tech 13:34: How to network as a founder vs a VC 17:31: Building a network in 2025 19:37: Cold Outreach 101 21:43: Andrew's favorite cold outreach template 24:41: Navigating cultural shock as an immigrant 29:10: How Andrew found gaps to build his business around 31:07: How to build a business for people's needs 34:06: Andrew's playbook on how underdogs can succeed in America 36:16: Behind the scenes of Fibe - Andrew's event-hosting business 41:12: What's next for Fibe 43:55: How to host better events 46:28: Andrew's favorite event-hosting format 47:15: Outro and closing thoughts 👉🏼 Resources: Link to Acquire.com: https://try.acquire.com/sharath/ 👉🏼 Where to find Andrew: Website: https://www.andrewyeung.co/ Linkedin: https://www.linkedin.com/in/andyeung Twitter: https://x.com/andruyeung 👉🏼 Where to find Sharath: Twitter: https://twitter.com/5harath YouTube: https://www.youtube.com/@5harath Website: https://5harath.com/ Newsletter: https://5harath.substack.com/ Founder Gigs: https://foundergigs.com/

December 19, 2024Episode 771 hr 7 min

Julian Weisser - Why ODF is on a mission of making things for people who make things!

👉🏼 About the Guests: Julian Weisser is a prominent entrepreneur, investor, and musician, best known as the co-founder and CEO of ODF/On Deck, a platform designed to support startup founders in launching and scaling their companies. Under his leadership, On Deck facilitated the launch of over 1,000 startups, significantly impacting the entrepreneurial landscape by providing resources and networking opportunities for aspiring founders. Julian is currently building Merge for microgrants, Stamp List to help job applicants who require visa sponsorship, and Builders Who Run, a run club based in SF. With a background in Music and Management from Berklee College of Music, Julian entered the startup world, co-founding Within Health, a company focused on using behavioral science to improve the lives of individuals with chronic conditions. In addition to his entrepreneurial endeavors, Weisser is an active angel investor, having backed over 50 startups across multiple industries, including decentralized finance and health tech. He is passionate about supporting innovative projects that aim to solve significant societal challenges. 👉🏼 About the Host: Sharath is a founder, creator, and community builder. He is also a serial maker who built and shipped 15+ projects using no-code tools. His SaaS product Shoutout generated $30k ARR, which was sold to a UK-based product studio. Prev, Sharath worked for world-changing startups like Product Hunt and On Deck, where he helped build and nurture communities. He also grew his audience on Twitter from 200 to 24,000 using give-first principles and creating high-value content. He recently sold his second SaaS product, GuestLab, and he is working on a startup idea while hosting this show. 👉🏼 Sponsor Corner: Shoutout to Acquire.com for sponsoring The Undefeated Underdogs podcast! They’re the best online marketplace to buy/sell startups and I know many founders who have sold their businesses there. If you're looking to wind down your business and cash in some of your founder chips, check them out - https://try.acquire.com/sharath/ 👉🏼 Description: Listen in as Sharath and Julian discuss building for people who make things, building community in 2025, how to work at a hypergrowth startup, and more! 👉🏼 Timestamps: 00:00: Episode Highlight 00:44: Shoutout to Acquire.com 03:09: Intro to Julian Weisser - Co-founder and CEO of ODF/On Deck 04:51: How Julian fell in love with startups 10:43: What founders can learn from musicians 15:01: How Julian built his very first startup 20:41: How On Deck went from a dinner series to a $20M Series A startup 27:07: Lessons from a hypergrowth startup 34:49: How can we build community in person in 2025? 37:33: Julian's project for people with big ideas: Merge 47:11: Julian's project for immigrants: Stamp List 51:17: How Julian started a run club in SF 55:45: Julian's projects in 2025 1:00:44: What should founders focus on? 1:06:13: Outro and closing thoughts 👉🏼 Resources: Link to Acquire.com: https://try.acquire.com/sharath/ 👉🏼 Where to find Julian: Website: https://weisser.io Linkedin: https://linkedin.com/in/julianweisser Twitter: https://x.com/julianweisser Newsletter and Podcast: https://textswithfounders.com/ On Deck: https://www.joinodf.com/ Merge: https://merge.club/ Stamp List: https://landing.club/stamplist Builders Who Run: https://weisser.io/runners 👉🏼 Where to find Sharath: Twitter: https://twitter.com/5harath YouTube: https://www.youtube.com/@5harath Website: https://5harath.com/ Newsletter: https://5harath.substack.com/ Founder Gigs: https://foundergigs.com/

December 11, 2024Episode 7654 min

Founders of Defang - Building the easiest way to develop, deploy and debug cloud apps in minutes!

👉🏼 About the Guests: Prakash and Lionello are the co-founders of Defang, a radically simpler way to develop, deploy, and debug production-ready cloud apps. Lionello is CTO at Defang, as well as an engineering lead and community organizer with EE and CS background and 20 years of international industry experience doing software and hardware. He has lived in Eindhoven, Bucharest, Beijing, Shanghai, Hong Kong, and recently moved to Vancouver BC. In 1997, he founded a virtual-reality software company, acquired by a multinational company for their real-time 3D rendering technology. In 2019, Workday acquired Trusted Key, the blockchain digital identity startup he helped found. Lio is active in the local maker communities, having been a staff member in China's first makerspace Xinchejian since its founding. Prakash serves as CEO at Defang. He co-founded & served as Chief Technology Officer, President & Board Member at Trusted Key Solutions. He brings experience from previous roles at Amazon Web Services (AWS), Workday, and Trusted Key. 👉🏼 About the Host: Sharath is a founder, creator, and community builder. He is also a serial maker who built and shipped 15+ projects using no-code tools. His SaaS product Shoutout generated $30k ARR, which was sold to a UK-based product studio. Prev, Sharath worked for world-changing startups like Product Hunt and On Deck, where he helped build and nurture communities. He also grew his audience on Twitter from 200 to 24,000 using give-first principles and creating high-value content. He recently sold his second SaaS product, GuestLab, and he is working on a startup idea while hosting this show. 👉🏼 Sponsor Corner: Shoutout to Acquire.com for sponsoring The Undefeated Underdogs podcast! They’re the best online marketplace to buy/sell startups and I know many founders who have sold their businesses there. If you're looking to wind down your business and cash in some of your founder chips, check them out - https://try.acquire.com/sharath/ 👉🏼 Description: Listen in as Sharath, Prakash, and Lio discuss building for builders, how frustration helped them create Defang, growth tactics, and more! 👉🏼 Timestamps: 00:00: Episode Highlight 00:44: Shoutout to Acquire.com 03:10: Intro to Lio and Prakash - co-founders of Defang, a radically simpler way to develop, deploy, and debug production-ready cloud apps. 05:29: Why Defang's mission is to help builders move faster 09:19: How frustration led to building Defang 15:01: Why big brands like AWS don't focus on builders 17:02: How to go from idea to MVP for a complex product 23:09: How Defang launched in the market and iterated using feedback 28:40: Defang's growth tactics to reach users 32:33: What made Prakash go from being a technical and engineering lead to a CEO? 34:55: Defang's Product Hunt launch 38:10: How Defang harnesses the power of AI 44:22: How to differentiate yourself from the competition 48:00: Important lessons from corporate and startups 50:56: Where is the app-creating environment going? 53:55: Outro and closing thoughts 👉🏼 Resources: Link to Acquire.com: https://try.acquire.com/sharath/ Defang's Product Hunt Launch: https://www.producthunt.com/posts/defang 👉🏼 Where to find Defang: Product Hunt Launch: https://www.producthunt.com/posts/defang Website: https://defang.io Linkedin: https://www.linkedin.com/company/defanglabs/ Twitter: https://twitter.com/DefangLabs Youtube: https://www.youtube.com/@DefangLabs Discord: https://discord.com/invite/nNjaJcJ25v Reddit: https://www.reddit.com/r/DefangLabs/ Github: https://github.com/DefangLabs 👉🏼 Where to find Prakash: Linkedin: https://www.linkedin.com/in/prakashsundaresan/ 👉🏼 Where to find Lio: Linkedin: https://www.linkedin.com/in/lionello/ Twitter: https://x.com/LioLunesu 👉🏼 Where to find Sharath: Twitter: https://twitter.com/5harath YouTube: https://www.youtube.com/@5harath Website: https://5harath.com/ Newsletter: https://5harath.substack.com/ Founder Gigs: https://foundergigs.com/

December 5, 2024Episode 751 hr 0 min

Brett Goldstein - How Micro is reinventing email and making it great again!

👉🏼 About the Guest: Brett Goldstein is the founder of Micro, an email-CRM blend so you can stay on top of your communications. He is also the co-founder of Launch House, which is a community built to connect and support the world's most ambitious entrepreneurs and creators. Launch House brings together emerging leaders in the startup and entertainment worlds to live in illustrious mansions around the world. Previously, he worked at Clearbit, Google, and Accenture, and graduated from the University of California, Berkeley. 👉🏼 About the Host: Sharath is a founder, creator, and community builder. He is also a serial maker who built and shipped 15+ projects using no-code tools. His SaaS product Shoutout generated $30k ARR, which was sold to a UK-based product studio. Prev, Sharath worked for world-changing startups like Product Hunt and On Deck, where he helped build and nurture communities. He also grew his audience on Twitter from 200 to 24,000 using give-first principles and creating high-value content. He recently sold his second SaaS product, GuestLab, and he is working on a startup idea while hosting this show. 👉🏼 Sponsor Corner: Shoutout to Acquire.com for sponsoring The Undefeated Underdogs podcast! They’re the best online marketplace to buy/sell startups and I know many founders who have sold their businesses there. If you're looking to wind down your business and cash in some of your founder chips, check them out - https://try.acquire.com/sharath/ 👉🏼 Description: Listen in as Sharath and Brett discuss building in a crowded market, the origin of Launch House, blending ambition and relationships, and more! 👉🏼 Timestamps: 00:00: Episode Highlight 00:42: Shoutout to Acquire.com 03:09: Intro to Brett Goldstein - founder of Micro, an email-CRM blend so you can stay on top of your communications. 04:33: Where Brett found his passion for startups 08:40: What inspires Brett to create? 10:10: Brett's first projects before Google 12:14: Why Brett chose startups and not music as a career 16:22: How Launch House turned from a reality show to a hacker house 20:28: How Brett went from a random tweet to building a network of founders at Launch House 22:43: How Brett pushes founders towards ambition AND relationship-building 25:20: How Brett took advantage of the crypto wave 27:59: What do most founders miss really easily? 33:02: Why Brett is choosing to reinvent email 40:12: How to avoid the downsides of a crowded market 43:01: Why Micro is creating an email-CRM blend 48:30: The problem-solving frameworks Brett used to build Micro 50:15: Brett's criteria for finding cofounders 52:43: Brett's cheatsheet to building a network in tech 54:30: How will AI impact the rise of startups and creative projects? 58:30: What Brett would build if not Micro 1:00:03: Outro and closing thoughts 👉🏼 Resources: Link to Acquire.com: https://try.acquire.com/sharath/ 👉🏼 Where to find Brett: Micro: https://www.micro.so/ Launch House: https://www.launchhouse.com/ Twitter: https://x.com/thatguybg Linkedin: https://www.linkedin.com/in/bgoldstein3/ Website: brettgoldstein.com Newsletter: https://socialstudies.substack.com/ 👉🏼 Where to find Sharath: Twitter: https://twitter.com/5harath YouTube: https://www.youtube.com/@5harath Website: https://5harath.com/ Newsletter: https://5harath.substack.com/ Founder Gigs: https://foundergigs.com/

November 27, 2024Episode 741 hr 15 min

Chrys Bader - A masterclass on the art of building viral consumer apps for the Internet!

👉🏼 About the Guest: Chrys is the co-founder at Rosebud, an AI-powered personal growth journal. He is a 6-time founder, founding Curio NFT Intelligence, Ikaria (social wellness), and Secret (social media). Prior to Secret, Chrys was a Product Manager at Google where he launched the photo-sharing community Photovine and contributed to Google+ and YouTube. He has built and launched several mobile social products such as Fliggo, TwitVid, Vidly and Treehouse. Chrys was born and raised near Boston and is a Y Combinator alumni. 👉🏼 About the Host: Sharath is a founder, creator, and community builder. He is also a serial maker who built and shipped 15+ projects using no-code tools. His SaaS product Shoutout generated $30k ARR, which was sold to a UK-based product studio. Prev, Sharath worked for world-changing startups like Product Hunt and On Deck, where he helped build and nurture communities. He also grew his audience on Twitter from 200 to 24,000 using give-first principles and creating high-value content. He recently sold his second SaaS product, GuestLab, and he is working on a startup idea while hosting this show. 👉🏼 Sponsor Corner: Shoutout to Acquire.com for sponsoring The Undefeated Underdogs podcast! They’re the best online marketplace to buy/sell startups and I know many founders who have sold their businesses there. If you're looking to wind down your business and cash in some of your founder chips, check them out - https://try.acquire.com/sharath/ 👉🏼 Description: Listen in as Sharath and Chrys discuss building in a saturated market, using AI as a thought partner, designing original apps, and more! 👉🏼 Timestamps: 00:00: Episode Highlight 00:45: Shoutout to Acquire.com 03:11: Intro to Chrys Bader - co-founder at Rosebud, an AI-powered personal growth journal 07:07: The experience of building a consumer app in mental health 11:14: How is Rosebud different from other AI companionship apps? 15:43: Where Chrys' love for mobile apps comes from 21:45: Why Chrys prefers building for consumers 25:43: Chrys' design inspiration for Rosebud 30:16: Building Rosebud as a designer and as a founder 33:10: How Chrys refuels himself after hard times in startup world 47:43: Chrys' advice for founders building consumer ideas and consumer apps 56:12: Fundraising vs bootstrapping in 2024 1:01:49: How Y Combinator changed Chrys as a founder and why he didn't go back 1:05:45: How Chrys went from social wellness to photo sharing to mental health apps as a founder 1:08:12: Rosebud's AI origin story 1:10:35: Where Rosebud is going next 1:14:42: Outro and closing thoughts 👉🏼 Resources: Link to Acquire.com: https://try.acquire.com/sharath/ Tyson Rosage: https://teamtreehouse.com/library/how-to-make-design-decisions-tyson-rosage 👉🏼 Where to find Chrys: Rosebud: https://help.rosebud.app/ Twitter: https://twitter.com/chrysb Linkedin: https://www.linkedin.com/in/chrysb Website: https://chrysbader.com/ 👉🏼 Where to find Sharath: Twitter: https://twitter.com/5harath YouTube: https://www.youtube.com/@5harath Website: https://5harath.com/ Newsletter: https://5harath.substack.com/ Founder Gigs: https://foundergigs.com/

November 14, 2024Episode 731 hr 3 min

Charlie Clark - How a solo founder took a side project from an idea to $300k+ ARR product!

👉🏼 About the Guest: Charlie Clark is a software engineer, creative coder, & bootstrapped founder who has grown his short links product, Liinks, to $25K MRR just 3 years after it officially launched. 👉🏼 About the Host: Sharath is a founder, creator, and community builder. He is also a serial maker who built and shipped 15+ projects using no-code tools. His SaaS product Shoutout generated $30k ARR, which was sold to a UK-based product studio. Prev, Sharath worked for world-changing startups like Product Hunt and On Deck, where he helped build and nurture communities. He also grew his audience on Twitter from 200 to 24,000 using give-first principles and creating high-value content. He recently sold his second SaaS product, GuestLab, and he is working on a startup idea while hosting this show. 👉🏼 Sponsor Corner: Shoutout to Acquire.com for sponsoring The Undefeated Underdogs podcast! They’re the best online marketplace to buy/sell startups and I know many founders who have sold their businesses there. If you're looking to wind down your business and cash in some of your founder chips, check them out - https://try.acquire.com/sharath/ 👉🏼 Description: Listen in as Sharath and Charlie discuss being a bootstrapped founder, building in a saturated market, making your side project a full time job, and more! 👉🏼 Timestamps: 00:00: Episode Highlight 00:35: Shoutout to Acquire.com 03:01: Intro to Charlie Clark - founder of Liinks, a beautiful link-in-bio page to gather your socials, music, videos, and more 04:52: Why is Liinks spelled with two ii's? 05:28: Why short links are better 07:35: Why Charlie set $25K MRR as a target to quit his full-time job 11:07: How Charlie designed Liinks to be clean, yet fun 15:41: How to convince people to buy your product 20:35: Learnings as a second-time founder 22:45: Why Liinks: Building in a saturated market 27:20: How to know if you want to commit to your project full-time 30:51: How to market in a saturated market 36:25: How to make creator-led products profitable 40:20: How Charlie made Liinks aesthetically pleasing 43:45: How working at Squarespace helped Liinks grow 48:45: Frameworks Charlie uses for growth, design, and user retention 50:10: How to balance user requests vs your own roadmap? 53:51: How will AI impact the future of Liinks? 58:08: Why Charlie chose the solo founder route 1:00:55: Why Charlie bootstrapped Liinks vs raising venture capital 1:02:53: Outro and closing thoughts 👉🏼 Resources: Link to Acquire.com: https://try.acquire.com/sharath/ 👉🏼 Where to find Charlie: Liinks: https://www.liinks.co/ Twitter: https://twitter.com/clarkcharlie03 Linkedin: https://www.linkedin.com/in/clarkcharlie03 vsual: https://www.vsual.co/closing Emoji Book: http://emojibook.club/ Colors of Motion: https://thecolorsofmotion.com/ 👉🏼 Where to find Sharath: Twitter: https://twitter.com/5harath YouTube: https://www.youtube.com/@5harath Website: https://5harath.com/ Newsletter: https://5harath.substack.com/ Founder Gigs: https://foundergigs.com/

November 6, 2024Episode 721 hr 18 min

Zachary Hamed - How using AI and design thinking made Clay the next generation rolodex!

👉🏼 About the Guest: Zach Hamed is a design-focused engineer who enjoys designing, building, and selling software. He is currently co-founder and co-CEO of Clay, a beautiful and private home for your personal and professional relationships. Previously, he helped build the product team at Goldman Sachs, co-founded a startup in the enterprise developer tools space, and writes blog posts. 👉🏼 About the Host: Sharath is a founder, creator, and community builder. He is also a serial maker who built and shipped 15+ projects using no-code tools. His SaaS product Shoutout generated $30k ARR, which was sold to a UK-based product studio. Prev, Sharath worked for world-changing startups like Product Hunt and On Deck, where he helped build and nurture communities. He also grew his audience on Twitter from 200 to 24,000 using give-first principles and creating high-value content. He recently sold his second SaaS product, GuestLab, and he is working on a startup idea while hosting this show. 👉🏼 Sponsor Corner: Shoutout to Acquire.com for sponsoring The Undefeated Underdogs podcast! They’re the best online marketplace to buy/sell startups and I know many founders who have sold their businesses there. If you're looking to wind down your business and cash in some of your founder chips, check them out - https://try.acquire.com/sharath/ 👉🏼 Description: Listen in as Sharath and Zach discuss going from a startup to corporate and back to startups, identifying A players, design thinking, and more! 👉🏼 Timestamps: 00:00: Episode Highlight 00:30: Shoutout to Acquire.com 02:56: Intro to Zachary Hamed - co-founder at Clay, a beautiful personal CRM, contact manager, and rolodex for people across industries who want to be more thoughtful with the people they know 05:35: Why Zach is building a startup in NYC vs Silicon Valley 10:38: Zach's experience going through the Thiel Fellowship 13:29: Going from building a startup to working at a large corporate 19:51: A process at Goldman Sachs that serves Zachary well today 25:15: Growth frameworks for Clay 33:53: How to spot and hire talent smarter than you 40:40: How to find A players 46:30: Why does Clay use .earth for their domain? 49:55: Why Zachary pursued a consumer-first approach 57:50: How AI is revolutionizing Clay's people-first approach 1:03:45: Using AI in Clay to catch up and schedule follow-ups 1:09:25: How Zach is building Clay using design thinking 1:17:35: Outro and closing thoughts 👉🏼 Resources: Link to Acquire.com: https://try.acquire.com/sharath/ Sparrow: https://sparrow.en.softonic.com/mac Mailbox: https://www.theverge.com/2015/12/8/9873268/why-dropbox-mailbox-shutdown Thiel Fellowship: https://thielfellowship.org/ 👉🏼 Where to find Zachary: Website: https://zmh.org/ Twitter: https://twitter.com/zmh Linkedin: https://www.linkedin.com/in/zacharyhamed Clay: https://clay.earth/ 👉🏼 Where to find Sharath: Twitter: https://twitter.com/5harath YouTube: https://www.youtube.com/@5harath Website: https://5harath.com/ Newsletter: https://5harath.substack.com/ Founder Gigs: https://foundergigs.com/

October 30, 2024Episode 7152 min

Brendan Mahony - Why founders should look at building startups as a game and not a business!

👉🏼 About the Guest: Brendan Mahony is the founder of Sunset, a company that helps tech companies shut down, saving founders thousands of dollars and hundreds of hours. He is also the ex-founder of Toybox (YC S18, acquired) and Contrast (shut down). From this experience, he built Sunset! 👉🏼 About the Host: Sharath is a founder, creator, and community builder. He is also a serial maker who built and shipped 15+ projects using no-code tools. His SaaS product Shoutout generated $30k ARR, which was sold to a UK-based product studio. Prev, Sharath worked for world-changing startups like Product Hunt and On Deck, where he helped build and nurture communities. He also grew his audience on Twitter from 200 to 24,000 using give-first principles and creating high-value content. He recently sold his second SaaS product, GuestLab, and he is working on a startup idea while hosting this show. 👉🏼 Sponsor Corner: Shoutout to Acquire.com for sponsoring The Undefeated Underdogs podcast! They’re the best online marketplace to buy/sell startups and I know many founders who have sold their businesses there. If you're looking to wind down your business and cash in some of your founder chips, check them out - https://try.acquire.com/sharath/ 👉🏼 Description: Listen in as Sharath and Brendan discuss raising money, finding customers at an early stage, weird startup ideas, and more! 👉🏼 Timestamps: 00:00: Episode Highlight 00:22: Shoutout to Acquire.com 02:47: Introduction to Brendan Mahony - founder of Sunset, a startup helping you shut down your startup correctly 04:33: Why create a startup about shutting down startups 10:00: How Brendan raised money as a first-time founder 19:05: How to get investors on board for your startup 20:50: Finding customers as an early-stage startup 25:20: Lessons from the first year of building Sunset 27:20: Building a startup at Y Combinator 32:34: How to bend the rules when you're in founder mode 38:16: How to deal with shutting down your startup - operationally, physically, mentally, emotionally 42:12: What would Brendan work on if not Sunset? 46:00: Weird startup ideas 48:25: Problems startups deal with 50:47: Outro and closing thoughts 👉🏼 Resources: Link to Acquire.com: https://try.acquire.com/sharath/ Andrew Gazdecki: https://www.andrewgazdecki.com/ 👉🏼 Where to find Brendan: Twitter: https://x.com/bmaho2211 Linkedin: https://www.linkedin.com/in/brendan-mahony-72929385 Sunset: https://www.sunsethq.com/ 👉🏼 Where to find Sharath: Twitter: https://twitter.com/5harath YouTube: https://www.youtube.com/@5harath Website: https://5harath.com/ Newsletter: https://5harath.substack.com/ Founder Gigs: https://foundergigs.com/

October 23, 2024Episode 7051 min

Ryan Gilbert - How to master the art of building and scaling curation newsletters!

👉🏼 About the Guest: Ryan Gilbert is the founder of Workspaces, a newsletter with nearly 14K subscribers, $2K MRR, and 45K subscribers on Twitter, all about the desks of creatives around the world, born during the pandemic. Workspaces was acquired by Loops in 2022, where Ryan was Head of Content, and re-acquired by Ryan for $1 in 2024. He has also worked at Product Hunt and has a new newsletter all about the best headlines across the internet, named H1 Gallery. 👉🏼 About the Host: Sharath is a founder, creator, and community builder. He is also a serial maker who built and shipped 15+ projects using no-code tools. His SaaS product Shoutout generated $30k ARR, which was sold to a UK-based product studio. Prev, Sharath worked for world-changing startups like Product Hunt and On Deck, where he helped build and nurture communities. He also grew his audience on Twitter from 200 to 24,000 using give-first principles and creating high-value content. He recently sold his second SaaS product, GuestLab, and he is working on a startup idea while hosting this show. 👉🏼 Sponsor Corner: Shoutout to Acquire.com for sponsoring The Undefeated Underdogs podcast! They’re the best online marketplace to buy/sell startups and I know many founders who have sold their businesses there. If you're looking to wind down your business and cash in some of your founder chips, check them out - https://try.acquire.com/sharath/ 👉🏼 Description: Listen in as Sharath and Ryan discuss side projects, building a personal brand, curation vs creation, and more! 👉🏼 Timestamps: 00:00: Episode Highlight 00:38: Shoutout to Acquire.com 03:06: Introduction to Ryan Gilbert - founder of Workspaces 04:41: Curation vs creation and how they're similar 06:35: How to develop taste 11:00: How to build a narrative around your taste 12:02: Current untapped content trends 15:58: The beginning of Workspaces 21:02: How side projects can change your life 22:25: Tactics for growing a newsletter 0 to 1 24:30: Experiments that didn't work for Workspaces 26:47: Improvements that Ryan is planning for Workspaces 28:38: Why sponsorships are harder now 32:08: Running experiments for sponsors 36:52: Ryan's content strategy at Loops - the email platform for SaaS 39:16: Low-cost content tips 40:47: Building a content strategy in 2024 43:54: Current trends people should pay attention to 44:46: How founders can build a personal brand 46:54: Ryan's experience as a new dad 49:46: Outro and closing thoughts 👉🏼 Resources: Link to Acquire.com: https://try.acquire.com/sharath/ 👉🏼 Where to find Ryan: Twitter: https://twitter.com/rjgilbert Website: https://www.workspaces.xyz/ Linkedin: https://www.linkedin.com/in/ryang1lbert/ 👉🏼 Where to find Sharath: Twitter: https://twitter.com/5harath YouTube: https://www.youtube.com/@5harath Website: https://5harath.com/ Newsletter: https://5harath.substack.com/ Founder Gigs: https://foundergigs.com/

October 16, 2024Episode 6957 min

Yana Welinder - How to build and scale a VC-backed startup as a solo founder!

👉🏼 About the Guest: Yana Welinder is CEO and Founder of Kraftful (YC S19) – an AI assistant that helps product teams build better products by listening to users at scale. Before starting Kraftful, she led product teams at multiple tech companies and personally experienced the challenge of trying to involve millions of users in the product development process. At Kraftful, she built a team of Meta, Slack, and IFTTT alumni, backed by Y Combinator, Google, Samsung, and other exceptional investors and entrepreneurs. Yana is also a Stanford fellow and has been invited to give talks at the White House, the UN Internet Governance Forum, Yale, NYU, and many product events and podcasts over the years. 👉🏼 About the Host: Sharath is a founder, creator, and community builder. He is also a serial maker who built and shipped 15+ projects using no-code tools. His SaaS product Shoutout generated $30k ARR, which was sold to a UK-based product studio. Prev, Sharath worked for world-changing startups like Product Hunt and On Deck, where he helped build and nurture communities. He also grew his audience on Twitter from 200 to 24,000 using give-first principles and creating high-value content. He recently sold his second SaaS product, GuestLab, and he is working on a startup idea while hosting this show. 👉🏼 Sponsor Corner: Shoutout to Acquire.com for sponsoring The Undefeated Underdogs podcast! They’re the best online marketplace to buy/sell startups and I know many founders who have sold their businesses there. If you're looking to wind down your business and cash in some of your founder chips, check them out - https://try.acquire.com/sharath/ 👉🏼 Description: Listen in as Sharath and Yana discuss founder mode, creating sticky products, mental health as a solo founder, and more! 👉🏼 Timestamps: 00:00: Episode Highlight 01:00: Shoutout to Acquire.com 03:26: Introduction to Yana Welinder - YC alum, solo founder at Kraftful – an AI assistant 05:01: How Yana discovered a niche for Kraftful 09:40: How to carry off a pivot, emotionally and tactically 15:52: Signals that indicate a need to pivot 18:30: Building a support system as a solo founder 19:50: Therapy frameworks that help solo founders 22:10: Habits to calm you down as a founder 25:51: How Y Combinator changes your startup journey 30:55: How Y Combinator has changed over the years 34:57: How to drive organic traction as a founder 41:45: Wearing many hats as a solo founder: hiring, growth, marketing, product 45:40: How to make your product sticky 48:22: Founder mode vs Manager mode 54:10: Yana's reply to "founder mode is trash" takes 56:58: Outro and closing thoughts 👉🏼 Resources: Link to Acquire.com: https://try.acquire.com/sharath/ Paul Graham: https://paulgraham.com/ Founder Mode: https://www.paulgraham.com/foundermode.html 👉🏼 Where to find Yana: Twitter: https://twitter.com/yanatweets Website: https://www.kraftful.com/ Linkedin: https://www.linkedin.com/in/ywelinder TechCrunch: https://techcrunch.com/author/yana-welinder/ 👉🏼 Where to find Sharath: Twitter: https://twitter.com/5harath YouTube: https://www.youtube.com/@5harath Website: https://5harath.com/ Newsletter: https://5harath.substack.com/ Founder Gigs: https://foundergigs.com/