Uploaded August 2025 | Updated September 2026, 3 hours ago
From co-founding Kik, which hit 300M users and 40% of U.S. teens, to building Substack into a $100M+ company, Chris Best has learned the hard truths of scaling, pivoting, and surviving in the startup world.
In this exclusive founder-to-founder conversation, Chris shares the real inflection points behind Substack’s growth, how his Kik experience shaped his decisions, why most startup advice should be ignored, and the mindset you must have if you want to survive the journey.
Whether you’re building your first startup or scaling your next big thing, these lessons will change how you think about growth, competition, and the day-to-day grind of being a founder.
📈 If you’re a founder, investor, or creator looking to scale, this is for you.
🚀 What You’ll Learn:
- The one founder mindset that wins long-term
- Why most startup advice isn’t worth following
- The real cost of scaling a $100M+ company
- Lessons from Kik’s 300M-user journey
💡 Are you a founder building the next big thing? Join Speedrun, the startup accelerator designed to help founders move fast with capital, mentorship, and top investors.
👉 Apply now: speedrun.a16z.com
📲 Follow us for more insights:
X (Twitter): https://x.com/speedrun
LinkedIn: linkedin.com/school/a16zspeedrun
Chapters:
0:00 – Kik to Substack Founder Story
0:36 – Substack Growth Inflection Points
1:38 – 3-Year Grind to Breakthrough
3:07 – Why Substack Built a Network
4:45 – Lessons from 300M Kik Users
5:53 – Competing with Big Platforms
8:44 – Challenges for Media Founders
10:34 – How to Start a Media Company
11:16 – Best & Worst Investor Advice
13:50 – Why to Ignore Most Rejections
15:37 – Startup Life Never Gets Easier
16:20 – Enjoy the Struggle
#startuplessons #substack #founderadvice #entrepreneurship #startuplife #scalingstartups #businessgrowth #startupmindset #techfounders
From co-founding Kik, which hit 300M users and 40% of U.S. teens, to building Substack into a $100M+ company, Chris Best has learned the hard truths of scaling, pivoting, and surviving in the startup world.
In this exclusive founder-to-founder conversation, Chris shares the real inflection points behind Substack’s growth, how his Kik experience shaped his decisions, why most startup advice should be ignored, and the mindset you must have if you want to survive the journey.
Whether you’re building your first startup or scaling your next big thing, these lessons will change how you think about growth, competition, and the day-to-day grind of being a founder.
📈 If you’re a founder, investor, or creator looking to scale, this is for you.
🚀 What You’ll Learn:
- The one founder mindset that wins long-term
- Why most startup advice isn’t worth following
- The real cost of scaling a $100M+ company
- Lessons from Kik’s 300M-user journey
💡 Are you a founder building the next big thing? Join Speedrun, the startup accelerator designed to help founders move fast with capital, mentorship, and top investors.
👉 Apply now: speedrun.a16z.com
📲 Follow us for more insights:
X (Twitter): https://x.com/speedrun
LinkedIn: linkedin.com/school/a16zspeedrun
Chapters:
0:00 – Kik to Substack Founder Story
0:36 – Substack Growth Inflection Points
1:38 – 3-Year Grind to Breakthrough
3:07 – Why Substack Built a Network
4:45 – Lessons from 300M Kik Users
5:53 – Competing with Big Platforms
8:44 – Challenges for Media Founders
10:34 – How to Start a Media Company
11:16 – Best & Worst Investor Advice
13:50 – Why to Ignore Most Rejections
15:37 – Startup Life Never Gets Easier
16:20 – Enjoy the Struggle
#startuplessons #substack #founderadvice #entrepreneurship #startuplife #scalingstartups #businessgrowth #startupmindset #techfounders
