The $2M Mistake: When Founders Hire Their First CFO Too Late

The $2M Mistake: When Founders Hire Their First CFO Too Late

Through compelling case studies and expert analysis, this series examines the critical timing mistakes founders make when scaling their financial leadership. Each episode dissects real stories of companies that faced severe consequences from delayed CFO hires, revealing the warning signs and lessons learned that every growing startup needs to know. This show produced by Aarish Shah.

Episodes

Prevention Playbook: Building Your Financial Leadership Timeline

January 8, 2025 • 10 mins
The series concludes with a comprehensive analysis of optimal CFO hiring timelines for different startup types and growth trajectories. We examine specific indicators that signal the need for professional financial leadership, common resistance points from founders, and how to structure the transition. The episode provides practical frameworks for evaluating financial leadership needs and avoiding the costly mistakes highlighted th...
Mark as Played

The Data Gap: Good Technology's Valuation Miscalculation

December 18, 2024 • 11 mins
This episode examines Good Technology's fatal valuation mistakes and the role that inadequate financial leadership played in its undervalued sale to BlackBerry. We analyze the specific financial modeling errors, the impact on employee stock options, and how proper financial oversight could have led to better outcomes. The episode provides detailed insights into the company's failure to accurately assess and communicate its true val...
Mark as Played

From Unicorn to Crisis: The Financial Unraveling of Fab.com

November 27, 2024 • 10 mins
This episode analyzes Fab.com's rapid rise and fall, focusing on how insufficient financial leadership contributed to its collapse. We examine the specific financial decisions between 2011-2015 that led to unsustainable burn rates, inventory management issues, and eventual failure. The episode details how proper financial oversight could have prevented the company's rapid cash depletion and guided more sustainable growth strategies...
Mark as Played

The Growth Trap: LendingClub's Financial Reporting Crisis

November 6, 2024 • 11 mins
This episode investigates LendingClub's 2016 crisis, focusing on how inadequate financial oversight led to serious reporting irregularities. We examine the specific financial control failures that occurred, the impact on investor confidence, and how earlier implementation of robust financial leadership might have prevented these issues. The episode provides detailed analysis of the loan sale misrepresentation scandal and its afterm...
Mark as Played

Scale Without Systems: Uber's Early Financial Management Challenges

October 16, 2024 • 11 mins
Focusing on Uber's pre-2015 period, this episode examines how the company's rapid global expansion without proper financial infrastructure created long-term challenges. We analyze specific instances where lack of financial controls led to international compliance issues, tax problems, and reporting inaccuracies. The episode highlights how delayed implementation of professional financial leadership impacted the company's ability to ...
Mark as Played

The Hidden Costs: Theranos' Financial Opacity and Investor Deception

September 25, 2024 • 11 mins
This episode analyzes how Theranos operated without proper financial leadership and controls, leading to one of the biggest startup frauds in history. We examine the specific financial reporting gaps between 2009-2015, the lack of proper audit trails, and how a qualified CFO might have prevented or exposed the deception earlier. The episode details the financial mechanisms that allowed the company to operate without proper oversigh...
Mark as Played

Burning Through Cash: Zenefits' Regulatory Compliance Nightmare

September 4, 2024 • 11 mins
Delving into Zenefits' rapid growth and subsequent regulatory crisis, this episode examines how the absence of strong financial leadership led to compliance oversights and mismanaged growth. We explore the specific compliance violations that occurred between 2014-2016, the cost of retroactive corrections, and the role a CFO could have played in preventing these issues. The episode provides detailed analysis of the company's insuran...
Mark as Played

The Million-Dollar Blind Spot: How WeWork's Financial Leadership Gap Led to Crisis

August 14, 2024 • 11 mins
This episode examines WeWork's early financial management challenges and how the absence of a seasoned CFO contributed to its failed IPO attempt. We analyze the company's complex financial structure between 2015-2017, the warning signs that emerged from insufficient financial oversight, and how earlier professional financial leadership might have prevented its valuation crisis. The episode highlights specific instances where lack o...
Mark as Played

Popular Podcasts

    Stuff You Should Know

    Stuff You Should Know

    If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

    Dateline NBC

    Dateline NBC

    Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

    On Purpose with Jay Shetty

    On Purpose with Jay Shetty

    I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

    Health Stuff

    Health Stuff

    On Health Stuff, hosts Dr. Priyanka Wali and comedian Hari Kondabolu tackle all the health questions that keep you up at night with hilarity and humanity. Together they demystify the flashy trends, and keep you informed on the latest research. You can rely on Health Stuff to bring you real, uninhibited, and thoughtful health talk of the highest caliber, and a healthy dose of humor.

    The Breakfast Club

    The Breakfast Club

    The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy, Jess Hilarious, And Charlamagne Tha God!

Advertise With Us
Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

Explore

iHeart

Live Radio

Podcasts

Artist Radio

Exclusives

News

Features

Events

Contests

Photos

Information

About

Advertise

Blog

Brand Guidelines

Contest Guidelines

Subscription Offers

Jobs

Get the App

Automotive

Home

Mobile

Wearables

© 2025 iHeartMedia, Inc.