What happens when the engineer companies call during a technical crisis finally gets to build something that is already working?

Misha Makara is the co-founder and CTO of Rally AI, an AI-powered platform positioning itself as a company’s first PR hire. After more than 15 years helping startups, venture portfolios, and enterprise teams solve technical failures—including work with Gaingels portfolio companies and the SEC-regulated digital securities platform tZERO—Misha is now tackling a different problem: managing demand from more than 200 companies waiting to use Rally without sacrificing product quality.

In Today's Episode We Discuss:

00:01 - Introducing Misha Makara and Rally AI

00:41 - Cybersecurity Roots and Kodak’s Digital Camera Legacy

02:26 - Experimental Design for Founders and Engineers

04:10 - From Wayfair and Dell to Startup Turnarounds

05:57 - Apollo Cameras and Black-and-White Barns

07:31 - Lessons From High-Volume Venture Portfolios

09:35 - Risk Cycles, Late-Stage Liquidity, and Early-Stage Investing

14:46 - Why More Features Fail to Save Startups

17:37 - Founder Coachability and the Ability to Pivot

19:50 - Bundling Risk From Hyperscalers and AI Platforms

22:27 - Why First-Mover Advantage Is Overrated

24:20 - AI Development Speed and the New Product Bottleneck

27:07 - Good Technical Debt vs. Bad Technical Debt

30:21 - Rally AI as a Startup’s First PR Hire

32:33 - Who Rally AI Works Best For

33:47 - Measuring PR Success and Building Media Relationships

35:11 - Rally AI’s Long-Term Vision

36:12 - The Three-Sided PR Marketplace

37:41 - Second-Mover Advantage and Disruptive Technology

41:25 - High-Signal Interviewing and Hiring Engineers

43:20 - When to Hire a Fractional CTO

Misha also shares the interview technique he uses to expose candidates who only know the textbook answer, the turnaround strategy that rescued a government software company, and the lesson his first mentor—one of the engineers behind Kodak’s digital camera—taught him about setting limits on every experiment.

Rally may be using AI to accelerate public relations, but Misha’s core philosophy is much older: define the destination, test deliberately, and know when it is time to take another road.

Pull quotes:

“Try to find a way to do less. Do the things that actually matter.”

“Hiring a fractional CTO to raise money—don’t do that. Bad, bad day.”

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