Are Entrepreneurs the Worst Planners? - Latest episode of The Web Talk Show
Latest Episode · #93 · 50:27

Are Entrepreneurs the Worst Planners?

Rebecca Irey, founder and CEO of Blue Skye Financial, explains why so many entrepreneurs skip financial planning and get hit with a surprise bill at year end, and how to pick an advisor who plans ahead.

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EP 093

Are Entrepreneurs the Worst Planners?

Rebecca Irey, founder and CEO of Blue Skye Financial, explains why so many entrepreneurs skip financial planning and get hit with a surprise bill at year end, and how to pick an advisor who plans ahead.

Sep 12, 2026 · 50:27 · with Rebecca Irey
Financial PlanningTaxesEntrepreneurship +2
EP 092

What You Don't Know About Your Email

Craig Taylor, co-founder of CyberHoot, explains why fake phishing tests that end in a meeting with HR can backfire, and how positive reinforcement helps employees spot real attacks.

Sep 9, 2026 · 48:15 · with Craig Taylor
CybersecurityEmail SecuritySecurity Awareness +2
EP 091

Be Your Own First Customer: The Power of Using Your Own Platform

Alberto Padilla, founder of Briq.mx, explains how he launched a regulated real estate crowdfunding platform in Mexico with a static site and a hand-updated progress bar, long before building any real infrastructure.

Aug 17, 2026 · 41:11 · with Alberto Padilla
CrowdfundingReal EstateFintech +2
EP 090

Growth Equity: An Insider's Look

Melanie Nabar, Principal at Volition Capital, explains how growth equity works and why raising a big round can still leave a founder with nothing at exit. She also covers when it makes sense to raise money and when to wait.

Jul 25, 2026 · 55:00 · with Melanie Nabar
Growth EquityVenture CapitalFundraising +2
EP 089

Why Throwing More Testers at an App Is Not Always Better

Pramin Pradeep, founder of BotGauge, explains why one company hired 25 QA testers and still hit only 56% coverage, and how AI agents change the math on software testing.

Jul 23, 2026 · 40:07 · with Pramin Pradeep
QASoftware TestingAI Agents +2
EP 088

He Built a Dating App That Has No Swiping (Here's Why)

Richard Decker, founder of Authenti, explains why his dating app drops swiping and public profiles, and why he thinks real connection should start before anyone sees your photo.

Jul 22, 2026 · 44:30 · with Richard Decker
Dating AppsEntrepreneurshipAI +2
EP 087

The One Tool That Replaces Your Whole Affiliate Stack

Alex Standiford, founder of Siren, explains how one incentive engine can run affiliate, referral, sales, and partnership programs without a pile of separate tools.

Jul 21, 2026 · 45:54 · with Alex Standiford
Affiliate MarketingReferral ProgramsSaaS +2
EP 086

The Truth About Company Knowledge. This Is What You're Missing.

Daniel Fallmann, founder of Mindbreeze, argues that most AI projects fail on business knowledge rather than the model. He explains why enterprise AI is really a knowledge problem.

Jun 12, 2026 · 53:43 · with Daniel Fallmann
Enterprise AIKnowledge ManagementRAG +2