The Startup Roadmap

Actionable advice to help you navigate your hardest inflection points, bridge the gap between vision and execution, and take charge of your startup's destiny.

The Startup Roadmap

Featured Insights

Embrace the MVP and Stop Trying To Boil The Ocean

Valuation Makes the Headlines, But Liquidation Preferences Allocate the Cash

You Are Ignoring 40% of Your Buyers

Bridge Rounds Rarely Save Startups

You Are Managing Two Runways, Not One

Don't Be the Hound. Pick Up Your Head.

The Complete Library

Embrace the MVP and Stop Trying To Boil The Ocean

Stop Setting Your Team Up to Fail

Where Did the Climate Seed Money Go?

You Are Managing Two Runways, Not One

The Q1 2026 VC Headline Is Lying to You

Three Guardrails That Keep Acquirers Honest During Diligence

Stop Protecting Your Org Chart

Avoid the Selective Board Disclosure Trap

The Exit Trap - Why Pausing Your Bridge Round Leads to a Fire Sale

Private Equity Won't Save Your SaaS Startup

The Collapsing Seat Economy Is Driving the SaaS-pocalypse

Headcount Is Not A Vanity Metric

Bridge Rounds Rarely Save Startups

You Are Ignoring 40% of Your Buyers

Where Did All the Venture Capital Go?

When One Sector Gets 64% of All VC Dollars, You Pay Attention

Your Board Meeting Isn’t Just an Update—It’s Your Moment to Lead

What's Your Ownership Stake Really Worth?

Navigating the 2025 Startup Valuation Reset

The Series A Squeeze – This is What a Tighter Fundraise Environment Looks Like

High Rates and Tariffs Are Delaying Startup Exits

Q1 VC Fundraising Tracks to Decade Low

When 71.1% of VC Dollars Go to One Sector, You Pay Attention

The Holiday Fundraising Trap – What Founders Should Do Now

Time Is Killing Venture Returns

Why Longer Fundraising Cycles Are Actually Good for Startups

The Rapid Rise of Zombie VCs

Getting from Series A to Series B

Unicorn bubbles

Your Mushroom Farm is Not a Tech Company

Census Data Highlights Surge in New Startups

The Team Skills Gap Assessment

The Team Skills Gap Assessment Workbook

Four Steps to Navigating the Startup Team Skills Gap

Avoid the Safe Note Dilution Trap

How To Steer Your Startup Through The VC Shakeout

Fear Uncertainty and Doubt Can Be Founder Superpowers

Are You Growing Fast Enough to Raise Your Next Round

Don't Believe The Hype

Down Rounds and Recaps Part 4 – Navigating the Startup Recap

Down Rounds and Recaps Part 3 – A Deep Dive into Down Rounds

Down Rounds and Recaps Part 2 – Managing Your Key Stakeholders

Down Rounds and Recaps Part 1 — What, Why, When

Staying True to Your Values - Learning from Substack's Crowdfunding Decision

From DTC to AI - Lessons in Navigating Business Model Shifts

The Ripple Effects of SVB's Failure on the Funding Landscape for Venture-Backed Companies

Mass Extinction Event for Startups? Are You Default Investable or Default Alive?

The Inevitable Pivot – 2 Traps You Must Avoid

Don't Be the Hound. Pick Up Your Head.

Lighten Up, Speed Up

Don't Trade Valuation For Structure

Inflation and Recession Are Coming For Your Contribution Margin! Here’s What You Need To Do.

Want to Create a Culture of Innovation? Ask These 3 Essential Questions.

4 Pitfalls of Raising VC and How To Avoid Them

Send It! Bad Advice In Mountain Biking and Startups

3 Essential Steps to Keep Enough Cash in the Bank

3 Common Mistakes That Are Inflating Your Marketing Budget

Don’t Let Selective Storytelling in the Media Warp Your Perspective

Wrong Sales Channels - Let's Fix That

Startup Restructuring 101 - Find Your Stop Doing Work

Down Round, Cram Down, or Wind Down. Difficult Decisions Ahead

External Events Can Move the Goalpost

Choose Your Venture Investors Wisely

Scaling Product-Market Fit is a Marathon, Not a Sprint

Stay in Control

The Casper IPO - Investor Leverage, The Hit to Employee Moral, and the Tough Road Ahead

Learning From the Casper IPO

Know Your Burn Rate - Set Up Your Assessment Framework

Defining Product-Market Fit - Feasible, Desirable, and Viable

Now You Know That Private Company Valuations Are Arbitrary

Gross Revenue Is A Vanity Metric