We Live to Build

Is AI coming for your job, or just the boring parts you hate? Tim Cakir, an AI consultant who scaled his agency to nearly $1M ARR in the first year, reveals why he believes "boring work" is the enemy of productivity and how AI agents can eliminate it. In this interview, Tim shares the controversial story of how he helped a company replace 50 employees with an automation tool, why he believes leaders are manufacturing AI fear, and how he built a fully automated sales CRM using Claude and Make.com. He also debates Sean on the future of "Vibe Coding" and why the future of work might just be a black terminal screen. Check out the company: https://aioperator.com

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📚 NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)

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▶ Get my eBook free - https://welivetobuild.com/network

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📈 WORK WITH ME

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▶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebook

▶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-call

▶ Startup Fundraising: https://welivetobuild.com/fundraising

▶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship

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👀 CONNECT WITH SEAN

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▶ LinkedIn: https://linkedin.com/in/seanweisbrot

▶ Inquiries: [email protected]

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🕒 CHAPTERS

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00:00 - Why Leaders Are Creating AI Fear

03:32 - The "10-Year Clock" Until Work Becomes Optional

06:20 - Will AI Kill Junior Jobs? (The Skill Gap Crisis)

09:30 - How to Document Your Processes for AI

12:12 - "Vibe Coding" vs. Building Real Systems

16:40 - Automating the "Boring Work" (Sales CRM Example)

20:53 - Sean's Struggle to Automate His Podcast

24:30 - Why I Love Working in the Terminal (No UI)

28:50 - The Future of AI Agents & Automation

33:40 - Firing 50 People: The Hard Truth About Efficiency

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Why do ad platforms like Meta and Google claim credit for sales they didn't actually generate? Scott Desgrossilliers explains why relying on ad platform data is like letting the "fox watch the henhouse" and how it leads businesses to burn cash on ineffective campaigns. In this interview, Scott and Sean discuss the complexities of multi-touch attribution, why you need an unbiased "source of truth" for your data, and how to lower your Customer Acquisition Cost (CAC) by feeding better signals back to ad algorithms. They also dive into the reality of buying a business vs. starting one, the importance of hiring for "grit," and why YouTube subscribers might be a vanity metric if you don't have an email list. Check out the company: https://wickedreports.com

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📚 NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)

----------------------------------------------------------------------------------------------------------------------------

▶ Get my eBook free - https://welivetobuild.com/network

-----------------------------------

📈 WORK WITH ME

-----------------------------------

▶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebook

▶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-call

▶ Startup Fundraising: https://welivetobuild.com/fundraising

▶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship

---------------------------------------------

👀 CONNECT WITH SEAN

---------------------------------------------

▶ LinkedIn: https://linkedin.com/in/seanweisbrot

▶ Inquiries: [email protected]

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🕒 CHAPTERS

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00:00 - Why Ad Platforms Lie About Your Sales

02:15 - How Conversion Tracking Actually Works (The "Fox in the Henhouse")

04:32 - The Difference Between First-Click & Last-Click Attribution

06:04 - Sean's Struggle with YouTube Ads & Subscribers

08:38 - Why You Need a Middle-of-Funnel Strategy (Email Lists)

16:04 - Buying a Business vs. Starting From Scratch

24:43 - The #1 Trait to Hire For: Grit & Persistence

29:30 - Hiring Mistakes: The MIT Graduate vs. The Doer

33:17 - How to Filter Candidates Before You Interview Them

36:36 - Lowering CAC by 40% with Better Data Signals

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How do you save a startup when growth flatlines? Itai Sadan, co-founder of Duda, reveals the two critical pivots that saved his company: shifting from mobile-only to responsive design, and the controversial decision to ignore 50% of his customers (small businesses) to focus entirely on agencies. In this interview, Itai explains why AI is the new SEO, how to optimize your website for ChatGPT search, and why the combination of AI and human creativity is the future of web design. He also shares the hard truth about competing with giants like Wix and WordPress and why founders must sometimes make painful decisions to survive. Check out the company: https://duda.co

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📚 NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)

----------------------------------------------------------------------------------------------------------------------------

▶ Get my eBook free - https://welivetobuild.com/network

-----------------------------------

📈 WORK WITH ME

-----------------------------------

▶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebook

▶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-call

▶ Startup Fundraising: https://welivetobuild.com/fundraising

▶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship

---------------------------------------------

👀 CONNECT WITH SEAN

---------------------------------------------

▶ LinkedIn: https://linkedin.com/in/seanweisbrot

▶ Inquiries: [email protected]

---------------------------

🕒 CHAPTERS

---------------------------

00:00 - Why Agencies Use Duda vs. WordPress/Wix

03:00 - The New SEO: Ranking on ChatGPT & AI Search

06:27 - Will AI Replace Web Designers?

09:30 - The Future: Voice AI Building Websites?

12:35 - The Hardest Part of Being a CEO (Constant Growth)

19:30 - Pivot #1: Mobile-Only to Responsive Design

22:20 - Pivot #2: Ignoring 50% of Customers (SMBs) to Focus on Agencies

26:40 - Surviving 2 Years of Flat Growth

31:50 - There is No Single Playbook for Success

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Why do the ultra-wealthy ignore the traditional 60/40 portfolio? Tad Fallows, founder of a high-net-worth community, reveals that his members hold almost zero bonds and use portfolio lines of credit instead of keeping cash reserves. In this interview, he breaks down the actual asset allocation strategies used by those with $5M-$100M+ net worths, including why they prioritize private equity and real estate over public bonds. Tad also explains why whole life insurance is almost never a good investment , the difference between revocable and irrevocable trusts for estate planning , and sophisticated tax strategies for selling concentrated stock positions—like Exchange Funds and Direct Indexing—without triggering a massive tax bill. Check out the company: https://longangle.com

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📚 NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)

----------------------------------------------------------------------------------------------------------------------------

▶ Get my eBook free - https://welivetobuild.com/network

-----------------------------------

📈 WORK WITH ME

-----------------------------------

▶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebook

▶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-call

▶ Startup Fundraising: https://welivetobuild.com/fundraising

▶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship

---------------------------------------------

👀 CONNECT WITH SEAN

---------------------------------------------

▶ LinkedIn: https://linkedin.com/in/seanweisbrot

▶ Inquiries: [email protected]

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🕒 CHAPTERS

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00:00 - Sudden Wealth: Why You Don't Need a Wealth Manager Yet

02:55 - High Net Worth Insurance (Umbrella & Carriers)

05:54 - Stop Buying Whole Life Insurance

08:33 - Estate Planning: Revocable vs. Irrevocable Trusts

11:25 - Are Offshore Trusts (Cook Islands) Worth the Risk?

14:46 - Asset Allocation: Why the Wealthy Don't Own Bonds

17:26 - The "Portfolio Line of Credit" Strategy (No Cash Drag)

20:23 - Private Equity vs. Public Markets

25:46 - How to Sell Concentrated Stock Without Taxes (Exchange Funds)

27:51 - Using Direct Indexing for Tax Loss Harvesting

29:16 - The 12-Month "Cooling Off" Rule for Windfalls

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Why should most startups avoid hiring a PR agency until after their Series A? Jackson Wightman, founder of a tech PR firm, argues that early-stage companies often waste money on agencies before they are ready. In this interview, he breaks down the right time to invest in public relations and why the playing field has tilted against those who ignore AI. Jackson also reveals how AI has fundamentally changed the agency model—allowing him to grow 15-20% without hiring junior employees. He discusses the problem of "AI Slop" in media pitches, the terrifying reality of a "lost generation" of workers who can't get entry-level experience, and how Chinese manufacturers are aggressively taking over Amazon's "Buy Box" by bypassing traditional branding. Check out the company: https://properpropoganda.net

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📚 NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)

----------------------------------------------------------------------------------------------------------------------------

▶ Get my eBook free - https://welivetobuild.com/network

-----------------------------------

📈 WORK WITH ME

-----------------------------------

▶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebook

▶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-call

▶ Startup Fundraising: https://welivetobuild.com/fundraising

▶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship

---------------------------------------------

👀 CONNECT WITH SEAN

---------------------------------------------

▶ LinkedIn: https://linkedin.com/in/seanweisbrot

▶ Inquiries: [email protected]

---------------------------

🕒 CHAPTERS

---------------------------

00:00 - How AI Changed the PR Industry Forever

01:32 - Why Your Startup Shouldn't Hire a PR Agency Yet

02:52 - The Plague of "AI Slop" in Pitch Emails

05:31 - Using AI for Media Training & Research

08:38 - Why We Stopped Hiring Junior Employees

10:48 - Is the Career Ladder Broken? (The Junior Talent Crisis)

13:21 - The Future of Work: Scared to Have Kids?

17:45 - How Chinese Brands Are Dominating Amazon

21:58 - Trust & Brand Equity: Why Product Isn't Everything

26:17 - The Translation Fail That Hurt a Game Launch

28:58 - The #1 Rule for Agency Success: Run by Numbers

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Is the $400 billion currently being poured into AI infrastructure a visionary bet or a massive bubble waiting to burst? Vijay Rajendran explains why we are seeing the biggest investment in fixed capital since the railroads, and what could cause it all to come crashing down. In this interview, Vijay and Sean discuss the new velocity of fundraising, where startups hit $100M ARR in months, and the rise of "seed-strapping" (raising once, then profiting). They also debate why VCs are obsessed with "founder pedigree," the structural reasons why European startups struggle to scale compared to the US, and the geopolitical shocks (food and fuel prices) that could abruptly end the AI party. Check out the company: https://gai.ventures

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📚 NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)

----------------------------------------------------------------------------------------------------------------------------

▶ Get my eBook free - https://welivetobuild.com/network

-----------------------------------

📈 WORK WITH ME

-----------------------------------

▶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebook

▶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-call

▶ Startup Fundraising: https://welivetobuild.com/fundraising

▶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship

---------------------------------------------

👀 CONNECT WITH SEAN

---------------------------------------------

▶ LinkedIn: https://linkedin.com/in/seanweisbrot

▶ Inquiries: [email protected]

---------------------------

🕒 CHAPTERS

---------------------------

00:00 - How AI Changed Fundraising Forever

00:40 - The Anomaly: 0 to $100M Revenue in 12 Months

04:02 - What is "Seed-Strapping"? (Profitable & Funded)

09:02 - The Pedigree Trap: Why VCs Obsess Over Stanford/Ex-OpenAI

10:07 - The Alumni Ventures Model

14:43 - Silicon Valley vs. Lisbon: Why Europe Can't Scale

17:32 - The Bureaucracy Problem in the EU

23:34 - The $400B Bet: Will the AI Bubble Burst?

27:32 - The "Geopolitical Shock" That Could Crash the Market

29:59 - How to Win Investor Money Right Now (Momentum)

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In the "Amazon Age," customers expect custom products yesterday. Eric Turney explains why businesses are now "forced to automate" or get left behind. In this interview, he reveals how Chinese manufacturers are using robotics to reduce factory lines from 50 workers to just 5 and why speed is now the most critical metric for survival. The conversation delves into the practical side of automation: using Monday.com to manage thousands of orders , implementing AI image editors to stay competitive , and the controversial rise of "Vibe Coding." Eric shares how he bypassed expensive developers to fix a critical website bug in 30 minutes using Claude AI , while Sean details how he built a functional SaaS tool using Cursor without writing the code himself. Check out the company: https://montereycompany.com

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📚 NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)

----------------------------------------------------------------------------------------------------------------------------

▶ Get my eBook free - https://welivetobuild.com/network

-----------------------------------

📈 WORK WITH ME

-----------------------------------

▶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebook

▶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-call

▶ Startup Fundraising: https://welivetobuild.com/fundraising

▶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship

---------------------------------------------

👀 CONNECT WITH SEAN

---------------------------------------------

▶ LinkedIn: https://linkedin.com/in/seanweisbrot

▶ Inquiries: [email protected]

---------------------------

🕒 CHAPTERS

---------------------------

00:00 - The State of Automation in E-Commerce

00:53 - How Robots Replaced 90% of Factory Workers

03:28 - Dialing in Manufacturing Processes in China

07:15 - Automating Order Management (Monday.com)

11:21 - The "Amazon Age": Why Speed is Everything

13:15 - Adopt AI or Get Left Behind

16:05 - Vibe Coding: Replacing Developers with AI

19:53 - Sean's Story: Building a SaaS App with Cursor

27:10 - Fixing Critical Bugs in 30 Minutes with Claude

32:38 - The Reality of Buying a Business (It's Hard)

34:36 - Why Culture is Your Best Retention Strategy

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Why did people turn down a $5,000 cash reward for referring a candidate? Dakota Younger discovered a strange psychological phenomenon while building his referral platform: offering money sometimes decreases motivation. In this interview, he breaks down the complex psychology of incentives, explaining why altruism often outperforms cash and how to structure a referral program that actually works. Dakota also explains why posting jobs is the least effective way to hire, the power of accessing passive talent through social capital, and the "Ice Cream Study" theory on why giving people too many choices leads to decision paralysis. Finally, he shares his most humbling lesson as a founder: admitting that he knows "absolutely nothing." Check out the company: https://goboon.co

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📚 NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)

----------------------------------------------------------------------------------------------------------------------------

▶ Get my eBook free - https://welivetobuild.com/network

-----------------------------------

📈 WORK WITH ME

-----------------------------------

▶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebook

▶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-call

▶ Startup Fundraising: https://welivetobuild.com/fundraising

▶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship

---------------------------------------------

👀 CONNECT WITH SEAN

---------------------------------------------

▶ LinkedIn: https://linkedin.com/in/seanweisbrot

▶ Inquiries: [email protected]

---------------------------

🕒 CHAPTERS

---------------------------

00:00 - Why Most Hiring Tools Fail (Employer-Centric)

01:39 - The Power of Social Capital in Referrals

04:10 - Why "Passive Talent" is the Gold Standard

06:27 - Hiring Remote Developers (Sean's Experience)

11:26 - How to Incentivize Referrals (Points vs. Cash)

16:34 - Why People Declined My $5,000 Cash Reward

18:34 - The Psychology of Altruism vs. Money

23:20 - The "Ice Cream Study": Why Less Choice is More

28:34 - Cultural Differences in Motivation (Asia vs. West)

31:35 - The #1 Lesson: "I Know Absolutely Nothing"

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Why did David Windley disrupt the recruiting industry by moving from commissions to an hourly model? In this interview, he reveals how he scaled his firm to $50 million in revenue before selling it. He explains why the traditional 33% commission model is broken for clients and how he implemented a professional services approach instead. David unpacks the terrifying reality of a 75% revenue drop during COVID and how furloughing staff saved the company. He also shares why he spun out a software startup (Hoot Recruit) to build AI agents for sourcing, the truth about whether AI will replace human recruiters, and his #1 rule for leadership: character over competence.Check out the company: https://iqrecruit.com

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📚 NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)

----------------------------------------------------------------------------------------------------------------------------

▶ Get my eBook free - https://welivetobuild.com/network

-----------------------------------

📈 WORK WITH ME

-----------------------------------

▶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebook

▶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-call

▶ Startup Fundraising: https://welivetobuild.com/fundraising

▶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship

---------------------------------------------

👀 CONNECT WITH SEAN

---------------------------------------------

▶ LinkedIn: https://linkedin.com/in/seanweisbrot

▶ Inquiries: [email protected]

---------------------------

🕒 CHAPTERS

---------------------------

00:00 - The $50M Exit & The Hardest Part 

00:41 - Surviving a 75% Revenue Drop During COVID 

03:11 - Rebuilding to $50M Revenue Post-Pandemic 

05:54 - Why I Sold the Business (The "Accidental Entrepreneur") 

06:06 - Hourly vs. Commission: Disrupting the Recruiting Model 

09:35 - Why the Industry Hates the Hourly Model 

12:42 - How to Generate $50M on Hourly Rates 

14:00 - Spinning Out "Hoot Recruit" Software  

16:35 - Using AI Agents for Candidate Sourcing 

19:26 - Will AI Replace Recruiters? (Human in the Loop) 

25:30 - AI Bias and Why Humans Are Still Needed 

27:26 - The #1 Leadership Rule: Character vs. Competence 

29:08 - Why Culture Matters More Than Policies

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Don't miss out on this game-changing Cursor technique designed specifically for AI entrepreneurs. While most use Cursor AI just for coding, there's a revolutionary way to manage your entire business, documents, emails, projects, and sales, directly within its interface, treating everything like code in a GitHub repository. In this demo, Seva Ustinov unveils this powerful workflow. Forget scattered AI tools; see how centralizing your company's context (strategy docs, meeting transcripts, competitor analysis) allows AI agents like Claude inside Cursor to automate huge portions of your non-coding work. Learn how this technique saves hours, increases accuracy, and could be the key to building a leaner, faster AI-driven business. Check out the company: https://ellyanalytics.com

----------------------------------------------------------------------------------------------------------------------------

📚 NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)

----------------------------------------------------------------------------------------------------------------------------

▶ Get my eBook free - https://welivetobuild.com/network

-----------------------------------

📈 WORK WITH ME

-----------------------------------

▶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebook

▶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-call

▶ Startup Fundraising: https://welivetobuild.com/fundraising

▶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship

---------------------------------------------

👀 CONNECT WITH SEAN

---------------------------------------------

▶ LinkedIn: https://linkedin.com/in/seanweisbrot

▶ Inquiries: [email protected]

---------------------------

🕒 CHAPTERS

---------------------------

00:00 - The Cursor Technique AI Entrepreneurs NEED to Know

01:27 - Why This Beats ChatGPT for Business Management

01:55 - LIVE DEMO: Managing Business Docs in Cursor AI

04:05 - Applying the Technique to Internal Company Ops

06:03 - Maintaining Context: Cursor vs. Chat Threads

07:14 - You're Still Responsible for the AI Output

08:31 - Building Your "Canonical" Knowledge Base in Cursor

11:35 - Using the Cursor Technique for Product Roadmapping

18:30 - How This Technique Enables Leaner Teams

19:10 - Managing Client Projects with the Cursor Technique

22:15 - Seva's AI Product: Automating Performance Marketing

31:58 - Why This Cursor Technique IS The Future of Work

38:05 - Demo: AI Marketing Agent Based on Cursor Context

46:03 - Automating Knowledge Extraction with This Technique

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