20 cold calls a day, $150 million in legal fees, and why the smartest CEOs are terrified of in-person competitors.

In this episode of Bricks, Bucks & Bytes, hosts Owen, Martin, Dustin, and Patric are joined by Justin Levine, CEO of  Shepherd, for a no-holds-barred discussion about the future of business, technology, and construction.

What we dive into:

• Apple's new AI call screening feature and why it spells doom for sales teams

• The shocking reality of 20 cold calls per day (and why most are terrible)

• Remote vs. office work: which startup would you fear more as a competitor?

• Why VCs are hilariously bad at cold outreach emails

• Construction insurance secrets that could save companies millions

• The $270 million Millennium Tower disaster (where legal fees cost more than the actual fix)

• Why hiring remotely means you need more experienced people

• The race to build the first $100 billion construction tech company

Key Quote: "If there's a competitor that's going to do exactly what we do - one fully remote, one five days in office - I am 100% more scared of the five day in office per week." - Justin Levine

From San Francisco's absurd delivery fees to the future of AI gatekeepers, this episode reveals uncomfortable truths about modern business that every entrepreneur needs to hear.

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Chapters

00:00 Intro

01:20 Introduction and Coffee Talk

04:20 Construction Assurance and Safety

07:31 iOS Updates and Cold Outreach Challenges

10:20 Innovations in Construction Insurance

13:23 Wrap-Up Policies and Cost Efficiency

16:22 Cold Outreach Strategies in 2025

19:11 The Future of AI in Sales and Marketing

28:01 The Importance of Mindset in Growth

28:39 Transparency in VC Interactions

29:27 Challenges of Cold Outreach in VC

30:24 The Role of Experience in Fundraising

33:54 Finding the Right Investor Fit

40:41 Understanding Investor Strike Zones

43:41 Defining Alpha in Venture Capital

44:59 The Long-Term Journey of Startups

47:42 The Bathtub Analogy in AI and Data Ownership

49:58 The Debate on Hustle Culture in Startups

50:22 The Value of In-Person Work Culture

58:59 The Challenges of Remote Work

01:08:15 Remote Work Considerations in Different Industries

01:09:11 Remote Work vs. Co-location in Tech and Hardware

01:11:42 The Impact of Time on Productivity

01:12:28 Rising Costs in Construction Insurance

01:16:32 The Challenges of Construction Defects

01:21:16 Reducing Insurance Premiums through Technology

01:26:59 Business Models in Construction Insurance

01:32:01 Future Trends in Construction Technology