Sitemaps
How We Secretly Lose Control of Our Startups
Does Startup Success Validate Us Personally?
Should Kids Follow in Our Founder Footsteps?
The Evolution of Entry Level Workers
Assume Everyone Will Leave in Year One
Was Mortgaging My Life Worth it?
What's My Startup Worth in an Acquisition?
When Our Ambition is Our Enemy
Are Startups in a "Silent Recession"?
Do Founders Deserve Their Profit?
The Utter STUPIDITY of "Risking it All"
Why Most Founders Don't Get Rich
Investors will be Obsolete
Why is a Founder so Hard to Replace?
We Can't Grow by Saying "No"
More Money (Really Means) More Problems
Committees Are Where Progress Goes to Die
Wait a Minute before Giving Away Equity
Why do Founders Suck at Asking for Help?
The Value of Actually Getting Paid
Will Investors Bail Me Out?
Is the Problem the Player or the Coach?
Do People Really Want Me to Succeed?
You Only Think You Work Hard
SMALL is the New Big — Embracing Efficiency in the Age of AI
The 9 Best Growth Agencies for Startups
Never Share Your Net Worth
This is BOOTSTRAPPED — 3 Strategies to Build Your Startup Without Funding
The Ridiculous Spectrum of Investor Feedback
$10K Per Month isn't Just Revenue — It's Life Support
Why do VCs Keep Giving Failed Founders Money?
If It Makes Money, It Makes Sense
The Hidden Treasure of Failed Startups
My Competitor Got Funded — Am I Screwed?
Why Having Zero Experience is a Huge Asset
How About a Startup that Just Makes Money?
How to Recruit a Rockstar Advisor
Risk it All vs Steady Paycheck
A Steady Hand in the Middle of the Storm
How to Pick the Wrong Co-Founder
Staying Small While Going Big
Why I'm Either Working or Feeling Guilty
Are Founders Driven by Fear or Greed?
What if I'm Building the Wrong Product?
How Startups Actually Get Bought
Quitting vs Letting Go
Actually, We Have Plenty of Time
Why Can't Founders Replace Themselves?
Who am I Really Competing Against?
Investors are NOT on Our Side of the Table
Plan for Bad Times, Budget in Good Times
Demo Article
When a $40m Exit is More Than a $200m Exit
Don't Fear the Reaper: AI Edition
Don't Let Investors Become Your Customer
We Can't Stay Out Of The Game For Too Long
What if Our Dreams Are an Illusion?
What if this isn't a "Big Business"?
Founders, Not All Problems Are Apocalyptic
Stop Listening to Investors
Can You Build a Startup in Less than 40 Hours per Week?
Unlocking the Power of a Startup Community
Strategies to Effectively Raise Capital for Your Startup Business
Are Bootstrapped Startups Less Valuable?
Why Founders Don't Ask for Help
Where to Find Startup Mentors to Take Your Business to the Next Level in 2023
What Is a Venture Capitalist and How Do They Work?
What Is an Entrepreneur? A 2023 Guide to Starting Your Own Business
A Guide to Different Stages of Funding for Startups
Time is Our Greatest Asset
The Toll of Everyone Around a Founder
Big Starts Breed False Victories
Once a Founder, Always a Founder
The Invention of the 20-Something-Year-Old Founder
When is Founder Ego Too Much?
Founder Impostor Syndrome Never Goes Away
Always Take Money off the Table
Should I Feel Guilty for Failing?
The Case Against Full Transparency
Why Do We Still Have Full-Time Employees?
This is Probably Your Last Success
How Many Deaths Can a Startup Survive?
How Should I Share My Wealth with Family?
Why Do VC Funded Startups Love "Fake Growth?"
Living the Founder Legend Isn't so Fun
Youth Entrepreneurship: Can Middle Schoolers be Founders?
How to get Customers for Startups
Founder Sacrifice — At What Point Have I Gone Too Far?
The Power of a Growth Mindset: How to Achieve Success in Your Startup
Startup Board Negotiations: How do I tell the board I need a new deal?
20 Best Kinds of Startups for 2023
Series A Funding Rounds
6 Similarities between Startup Founders and Pro Athletes
Choosing The Right Type Of Website For Your Business
Startup Failure is just One Chapter in Founder Life
What If my plan for retirement is "never retire"?
Is Quiet Quitting a Problem at Startup Companies?
If a Startup Sinks, Founders Go Down With it
Startup Growth Challenges: The Downfall of Becoming Internally Focused
Analyzing Startup Accounting Results

Good things happen when you’re helpful

Doug Crescenzi

Good things happen when you’re helpful

1*IdAiAhzSD24b4PI1s-RmMA

Five years ago I dropped out of a PhD program and started my first company. I had no idea what I was doing and made every mistake you could imagine. Needless to say that business didn’t last very long.

Since then I’ve gone on to start three more companies — one venture-backed, two service-based — each with varying levels of success and failure.

From these experiences there’s one lesson I’ve learned that’s remarkably simple, exceedingly powerful and virtually universal: good things happen when you’re helpful.

Clear a path and make others look good

I was recently introduced to Ryan Holiday’s “canvas strategy”. In short, his “canvas strategy” speaks to the notion of identifying mentors and actively finding ways to support them and their missions. It’s about being humble, doing the dirty work, making them look good and learning from your experiences along the way.

“Find and make canvases for other people to paint on.”

This apprentice model has proven tremendously successful throughout history. Holiday describes the best apprentices as the ones who are able to “clear a path” for their mentors.

“The Roman’s had a loose word for the concept: anteambulo and it meant a person who cleared the path in front of their patron. If you can do that successfully, you secure a quick and educational power position.”

However, many of us nowadays are too anxious to lead. That or we lack the humility to do the unsexy work that no one else wants to do. Yet the reality is if you clear a path for others, you ultimately help steer its course. At the same time you create a unique path for yourself.

So, how should you go about instituting your own “canvas strategy”?

Identify opportunities to compliment the skills of others — remove their distractions — save them time

When it comes to being helpful and instituting your own canvas strategy, you should attach yourself to people and organizations who are already successful. Additionally, you should hone in on the shortcomings they have that you can address with your strengths.

If you can identify the right people and organizations where your strengths will compliment their weaknesses, you’ll be well-positioned to make them even more successful. At the same time you’ll see first hand how they operate, the diverse problems they solve and why they do things the way they do.

Complimentary skill sets however aren’t always enough. Sometimes it’s a matter of doing what needs to get done. I.e., helping them save time and removing distractions that will hinder their progress and focus. This may not involve the most compelling set of tasks and responsibilities, but it’s an investment in your development that’s worth making.

Invest in the long-term

Too often too many of us feel entitled to success. Our egos cloud our judgement and stymie our progress. The canvas strategy, however, requires modesty and patience.

To successfully institute the canvas strategy you have to be willing to set aside your ego. It’s a long-term investment and there are significant and meaningful returns to be had.

Be comfortable playing the long game.

Help your mentors who you respect and admire succeed overtime and in parallel learn how they lead, operate and execute from within their organizations. This will present you a highly unique and vivid picture into the underlying characteristics and systems that ultimately make them successful.

“Greatness comes from humble beginnings; it comes from grunt work. It means you’re the least important person in the room — until you change that with results.” — Ryan Holiday

We approach our work with our clients in this way. That is to say, we strive to clear a path for them, compliment their weaknesses with our strengths, and invest in their long-term growth and success.

It’s rewarding work, but at the end of the day we’re entitled to nothing.

Therefore, it’s paramount we make ourselves indispensable and constantly seek to identify new canvases upon which they can paint. It’s remarkably simple, exceedingly powerful and virtually universal.

Good things happen when you’re helpful.


Also shared on Upstate Interactive.

Find this article helpful?

This is just a small sample! Register to unlock our in-depth courses, hundreds of video courses, and a library of playbooks and articles to grow your startup fast. Let us Let us show you!

Submission confirms agreement to our Terms of Service and Privacy Policy.

Already a member? Login

No comments yet.

Register to join the discussion.

Already a member? Login

Create Free Account