The Undefeated Underdogs

👉🏼 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/

👉🏼 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/

👉🏼 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/

👉🏼 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/

👉🏼 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 Chris discuss content creation, why Chiefs of Staffs aren't great for early-stage startups, and more!
 
👉🏼 Timestamps:

• 00:00: Episode Highlight
• 00:40: Shoutout to Acquire.com
• 03:08: Introduction to Chris Hladczuk - Yale alum, investment banker, content creator, founder
• 07:00: Chris' lessons learned as a content creator
• 10:37: The tactical stuff: going from idea -> first draft -> finished content
• 14:00: A starter guide to becoming a content creator
• 17:45: Benefits of writing content for 4+ years
• 19:30: What the early days of content creation are like
• 21:55: Chris' journey from Yale to Goldman Sachs to tech startups
• 24:17: How to start questioning the status quo
• 25:54: How Chris deals with lows, failures, and rejection
• 28:22: Why sports & startups are the same
• 31:35: Chris' experience at Goldman Sachs
• 33:15: Why Chris left Goldman Sachs
• 34:20: How Goldman Sachs actually helped Chris build a startup
• 37:25: Why Chris chooses not to be a full-time content creator
• 38:49: How to pick which startup to work at
• 40:30: Being an individual contributor vs a Chief of Staff
• 42:25: The best hard skills to learn
• 44:50: Chris' experience at Meow
• 47:52: How Chris developed the conviction to start his own company
• 51:22: The experience of building a complete product
• 54:20: Chris' new startup, Hanover: a co-pilot for VCs
• 57:09: Building in public vs building in stealth
• 58:14: Fundraising 101
• 59:15: How AI is changing the world in 2024
• 1:01:04: Defining excellence in startups

👉🏼 Resources:

• Link to Acquire.com: https://try.acquire.com/sharath/
• Jack Butcher: https://twitter.com/jackbutcher
• Paul Graham: https://paulgraham.com/
• Meow: https://www.meow.com/
• Tim Ferriss: https://tim.blog/

👉🏼 Where to find Chris:

• Twitter: https://twitter.com/chrishlad
• Website: https://chrishlad.com/
• Linkedin: https://www.linkedin.com/in/chris-hladczuk-b09204153
• Hanover: https://www.hanover.co/

👉🏼 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/