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- Beyond Founder-Friendly: How Portfolio Size Shapes Investor Value (And Why I Changed My Mind)
Beyond Founder-Friendly: How Portfolio Size Shapes Investor Value (And Why I Changed My Mind)
π Quick heads up: This newsletter challenges everything you think you know about portfolio management. Including what I thought I knew.
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What you'll learn:
Why conventional wisdom about portfolio size and founder support is fundamentally flawed
A counterintuitive approach that turns large portfolios into an advantage
A practical 2-hour framework for delivering systematic value at any scale
Remember when I said large portfolios = worse founder support?
Yeah, about that...
The Story: When Size Becomes Strength
Remember when I said large portfolios = worse founder support? Yeah, about that...
"Wholeheartedly disagree that this is the trade-off," Philipp MΓΆhring, founder of Tiny VC, responded to that email. "You can have a small portfolio and be very aggressive vs founders, meddling and micro-managing, and you can have a large portfolio, focus on your strengths and trust the founder with other things."
Following up from that exchange, two hypotheses emerged from a lunch conversation last week:
Most investors struggle to provide any real proactive value
When they do invest time, the ROI is usually unclear
The Insight: Quality Over Quantity
The conventional formula is broken:
More portfolio companies β less value
Less attention β worse support
Portfolio size = potential leverage
Instead, focus on:
Pick your superpower (one thing you're genuinely great at)
Build a system to deliver it consistently
Let your portfolio/community size amplify your impact
π οΈ Want to implement this tomorrow? Here's your playbook:
The Quick Win: Your 2-Hour Value Engine
Step 1: Audit Your Value (30 mins)
List every founder interaction from last month
Circle the ones that actually moved the needle
Find the pattern (hint: it's not the "catch-up calls")
Step 2: Pick Your Lane (30 mins)
Choose ONE thing you do better than 90% of investors
Make it specific (not "hiring help" but "3 VP Engineering intros in 14 days")
Write down exactly how you'll deliver it
Step 3: Build Your System (1 hour)
Create a simple intake form
Set up your delivery workflow
Test with 3 portfolio companies
π« What doesn't work:
Random "how can I help?" emails
Generic networking events
Being everyone's therapist
β What does:
Specific, measurable support
Systems that scale
Focused expertise
The future of venture support isn't about time spent β it's about value delivered.
Want to dive deeper? Reply with "INVESTOR," and I'll send you my 25-page investor reflection guideβhot off the press!
PS: Yes, of course, you are building a concentrated industry portfolio with deep knowledge in a specific industry, geo, or business model. Keep it going. You will still likely end up with 20+ portfolio companies in every fund. So the above applies to you, too.
Interested in more of my work?
If youβve made it this far, perhaps youβd be interested in my other writing and resources:
1. Most read all time: Why I Stopped Using OKRs
2. Most read Q4: Clarity, Leverage, Resilience: The Secret Sauce of High-Growth CEOs
3. New Cheat Sheets every month, full collection in this FOLDER. (16 in total, +4 since last time)
Want to work with me as a Coach & Catalyst for your business? Schedule a call HERE.
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