Screensharing $90M of Startup Finance Lessons in 32 Minutes
The Startup Ideas Podcast
Speak Both Languages: Cash vs Accrual
Greg explains why founders must understand cash basis for survival and accrual for investors.
Master Your Cashflow (Templates Included): https://startup-ideas-pod.link/money-map
On this episode, I share my simple financial operating system that helps me run my business. I share actual workflows that have saved one of my portfolio company from an 11-week runway crisis (when they thought they had 8 months), and the templates behind his 13-week cash tracker, Bear/Base/Bull decision framework, and one-page board report. This is a rare look inside the tactics I use to think about cash flow, dilution strategy, and building companies that don't run out of runway by accident.
Bank with Brex: https://startup-ideas-pod.link/brex-sip
Timestamps
00:00 – Intro: The whiteboard that saved two companies
02:08 – The Financial Rhythm: Daily, weekly, monthly cadence
03:23 – Rule 1: The 13-Week Cash Flow System
06:10 – Rule 2: Cash vs. Accrual
08:14 – Rule 3: Extend Runway
12:13 – Rule 4: Be Exit Ready
15:06 – Rule 5: Cards and Credit
18:01 – Rule 6: Track 5 Weekly Metrics
20:00 – Rule 7: The Monthly One-Pager
21:12 – Rule 8: Tools and Automation
26:11 – Rule 9: Dilution Mindset
27:59 – How to implement: The weekly rhythm in practice
29:31 – Action plan and closing
Key Points
Your P&L lies about survival—one portfolio company thought they had 8 months of runway but actually had 11 weeks when mapped to real cash flow
The Bear/Base/Bull decision framework prevents emotional spending: if two-plus scenarios say no, wait (a $60K conference booth was rejected in bear case, approved two months later in bull case)
Acquisitions happen in 48 hours—keep a 10-file data room updated quarterly so you can respond to Tuesday emails with Wednesday meetings
Trust doesn't scale, policy does: weekly corporate card reviews caught an $8K personal ad spend in 7 days instead of 30
The system runs itself once built: 15 minutes Monday + 30 minutes Friday + 4 hours/month replaces heroic monthly scrambles
Every dollar raised costs ownership forever—cutting $40K/month burn has the same 12-month runway impact as fundraising but with 0% dilution
The #1 tool to find startup ideas/trends - https://www.ideabrowser.com
LCA helps Fortune 500s and fast-growing startups build their future - from Warner Music to Fortnite to Dropbox. We turn 'what if' into reality with AI, apps, and next-gen products https://latecheckout.agency/
Boringmarketing - Vibe Marketing for Companies: boringmarketing.com
The Vibe Marketer - Join the Community and Learn: thevibemarketer.com
Startup Empire - get your free builders toolkit to build cashflowing business - https://startup-ideas-pod.link/startup-empire-toolkit
Become a member - https://startup-ideas-pod.link/startup-empire
FIND ME ON SOCIAL
X/Twitter: https://twitter.com/gregisenberg
Instagram: https://instagram.com/gregisenberg/
LinkedIn: https://www.linkedin.com/in/gisenberg/
The AI-powered Podcast Player
