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I’ve led over 200 investments… and the best founders all had one thing in common:
They knew why they were building the business.
When I meet a founder, I’m not investing in my own vision.
I’m underwriting their vision, and whether they have the clarity, energy, and drive to make it real.
So I listen for:
✔️ Why this product
✔️ Why this problem
✔️ Why now
✔️ Why you
Most pitches talk about the product too much.
The great ones tell a story only that founder could tell.
If you're thinking about raising venture and want to sharpen your pitch… I’ve opened up a few 1:1s on @useintro to help.
The link to book is in my profile! All proceeds are donated to dog rescue.
They knew why they were building the business.
When I meet a founder, I’m not investing in my own vision.
I’m underwriting their vision, and whether they have the clarity, energy, and drive to make it real.
So I listen for:
✔️ Why this product
✔️ Why this problem
✔️ Why now
✔️ Why you
Most pitches talk about the product too much.
The great ones tell a story only that founder could tell.
If you're thinking about raising venture and want to sharpen your pitch… I’ve opened up a few 1:1s on @useintro to help.
The link to book is in my profile! All proceeds are donated to dog rescue.
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An investor can disagree with a founder and still be firmly in their corner.
Actually, I think being able to have that conversation is part of a healthy relationship.
The goal is to care enough about the outcome that both people can be honest.
Actually, I think being able to have that conversation is part of a healthy relationship.
The goal is to care enough about the outcome that both people can be honest.
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Why do we expect founders to become M&A experts the first time they sell a company?
The buyer may have done this ten times. The founder may be learning every step while still running the business.
Getting help seems like a pretty sensible response to that gap. I’d worry more about the founder who thinks they should already know everything.
The buyer may have done this ten times. The founder may be learning every step while still running the business.
Getting help seems like a pretty sensible response to that gap. I’d worry more about the founder who thinks they should already know everything.
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I got a good question after posting that I’m a big fan of small VC funds:
How can a small fund protect its ownership when a breakout company raises a large follow-on round?
In summary, it usually doesn’t need to.
Normal dilution is part of venture investing. If the company continues growing quickly and its valuation increases, owning a slightly smaller percentage can still produce a fantastic outcome.
The value of the ownership matters more than maintaining the exact percentage. ✨
How can a small fund protect its ownership when a breakout company raises a large follow-on round?
In summary, it usually doesn’t need to.
Normal dilution is part of venture investing. If the company continues growing quickly and its valuation increases, owning a slightly smaller percentage can still produce a fantastic outcome.
The value of the ownership matters more than maintaining the exact percentage. ✨
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I’m working on something related to small VC funds that I hope to launch within the next few weeks. ✨
If you already invest in multiple funds under $50M, I’d love to chat and trade notes.
I’m especially interested in how you evaluate emerging managers, build a portfolio across funds, and think about the long tail of early-stage VC.
What has worked well? What have you learned? What would you do differently today?
If you already invest in multiple funds under $50M, I’d love to chat and trade notes.
I’m especially interested in how you evaluate emerging managers, build a portfolio across funds, and think about the long tail of early-stage VC.
What has worked well? What have you learned? What would you do differently today?
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I'd love to hear your general thoughts on joining social clubs, membership organizations, and/or affinity networks that have annual fees and structured events.
Since I am relatively new to Nashville and broadening my horizons beyond just VC, I am thinking of joining one to meet people across a range of industries.
Have you found it to be a good experience? ✨
Since I am relatively new to Nashville and broadening my horizons beyond just VC, I am thinking of joining one to meet people across a range of industries.
Have you found it to be a good experience? ✨
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A founder call is a two-way evaluation.
Founders should also ask questions.
Ask:
- how the investor makes decisions
- what support looks like after the check
- which companies received the most attention and why
- what happens when the company misses a plan.
You are learning whether the relationship fits your company, your pace, and your definition of success. A good call leaves both sides with a clearer picture, even when the answer is no.
Founders should also ask questions.
Ask:
- how the investor makes decisions
- what support looks like after the check
- which companies received the most attention and why
- what happens when the company misses a plan.
You are learning whether the relationship fits your company, your pace, and your definition of success. A good call leaves both sides with a clearer picture, even when the answer is no.
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Supporting a portfolio through the later stages looks very different from sourcing new investments.
My time now includes strategy conversations, introductions, exit preparation, reporting, and plenty of administrative details.
There is rarely one dramatic intervention.
It is mostly a series of small promises kept over many years. ✨
My time now includes strategy conversations, introductions, exit preparation, reporting, and plenty of administrative details.
There is rarely one dramatic intervention.
It is mostly a series of small promises kept over many years. ✨
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A bootstrapped company can’t always afford to keep a bad customer.
Yes, you need the revenue. But count the hours spent on custom requests, the invoices you’re chasing, and the customers you couldn’t support because this one consumed the week.
Sometimes the account you’re afraid to lose is making it harder to build the business you actually want.
Yes, you need the revenue. But count the hours spent on custom requests, the invoices you’re chasing, and the customers you couldn’t support because this one consumed the week.
Sometimes the account you’re afraid to lose is making it harder to build the business you actually want.
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"Too early to think about an exit” is bad advice.
Too early to sell? Maybe.
But knowing who might buy your company, why they’d want it, and what would make it valuable to them can improve the business you’re building today.
Too early to sell? Maybe.
But knowing who might buy your company, why they’d want it, and what would make it valuable to them can improve the business you’re building today.
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As an investor and dog rescuer, my jaw is on the floor.
- Warhound just raised $200M at a $1.2B valuation
HUH? Is this proven? Or is VC getting even crazier and throwing money at anything at this point?
-If we're investing this kind of money to fill the gap in non-human assistance in war and first responding, are robots or drones or other non-living "beings" an option?
-Have you seen all the press this year with multiple K9 handlers allowing their dogs to die in hot cars? That's just one example of what could go wrong (not to mention the process of rehoming them at the end of their "service" if they make that it that far)
-How are we shutting down beagle testing labs in the US (finally) and now we see this pop up?
❓ I'm curious what others in my network think about this. I've read lots of takes on both sides. Ethical or no? Good idea or no?
- Warhound just raised $200M at a $1.2B valuation
HUH? Is this proven? Or is VC getting even crazier and throwing money at anything at this point?
-If we're investing this kind of money to fill the gap in non-human assistance in war and first responding, are robots or drones or other non-living "beings" an option?
-Have you seen all the press this year with multiple K9 handlers allowing their dogs to die in hot cars? That's just one example of what could go wrong (not to mention the process of rehoming them at the end of their "service" if they make that it that far)
-How are we shutting down beagle testing labs in the US (finally) and now we see this pop up?
❓ I'm curious what others in my network think about this. I've read lots of takes on both sides. Ethical or no? Good idea or no?
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Here's an article about the raise announcement:
techcrunch.com/2026/10/22/ben…
techcrunch.com/2026/10/22/ben…
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We celebrate founders for refusing to quit, then act surprised when they stay too long in a business that no longer makes sense.
Persistence deserves respect.
So does recognizing when your next five years would be better spent building something else.
Persistence deserves respect.
So does recognizing when your next five years would be better spent building something else.
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An exit can be an IPO, large M&A, small M&A, a PE roll-up, or an acquihire.
Each path asks different questions:
✨Who is the buyer?
✨Which customer problem has become valuable?
✨Can the team explain the product without a 40-slide deck?
✨Are the ownership records clean enough for someone else to understand?
Founders!! You don't need to predict the buyer on day one. Just build something durable enough that several kinds of buyers can see the value.
Each path asks different questions:
✨Who is the buyer?
✨Which customer problem has become valuable?
✨Can the team explain the product without a 40-slide deck?
✨Are the ownership records clean enough for someone else to understand?
Founders!! You don't need to predict the buyer on day one. Just build something durable enough that several kinds of buyers can see the value.
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An investor’s advice should help a founder make a better decision.
To give useful advice, you need to know the company, what it’s been through, who’s involved, and what they’ve already tried.
Without that understanding, you’re mostly sharing an opinion.
To give useful advice, you need to know the company, what it’s been through, who’s involved, and what they’ve already tried.
Without that understanding, you’re mostly sharing an opinion.
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Portfolio support is rarely one big strategic gesture.
It's a series of small actions:
- reading the update
- making a thoughtful introduction
- asking the difficult question
- reviewing the plan
- answering the call when things go wrong
None of this is glamorous. All of it compounds.
It's a series of small actions:
- reading the update
- making a thoughtful introduction
- asking the difficult question
- reviewing the plan
- answering the call when things go wrong
None of this is glamorous. All of it compounds.
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The updates I value most are often the uncomfortable ones. That’s usually when an investor can actually be useful.
Every relationship runs on trust and communication. VC and CEO is no different.
The founders I trust most send a monthly update when things are bad, not just when they're good.
Bad news early builds trust. Surprises destroy it.
Trust is what gets you the follow-on check.
Founders: what's the hardest update you ever sent your investors?
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Why is exit planning important for VC backed companies??
Because only about one-third of them will return cash and have a shot at making the founders & investors money.
Only one-third!!
And I'd guess that only 10-15% of all VC-backed businesses yield good or great outcomes for founer 14 years in VC, I believe all founders should have an exit plan.
Because only about one-third of them will return cash and have a shot at making the founders & investors money.
Only one-third!!
And I'd guess that only 10-15% of all VC-backed businesses yield good or great outcomes for founer 14 years in VC, I believe all founders should have an exit plan.
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I just landed in San Francisco to speak at the Solo GP conference today and keynote a founder seminar on exit planning tomorrow.
I hope I get to see lots of my VC friends over the next 2 days!!! ✨
I hope I get to see lots of my VC friends over the next 2 days!!! ✨
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If $500K gets the company where it needs to go, there is no prize for raising $5M.
Every extra dollar comes with dilution, expectations, and less control over what happens next.
Raise enough to reach the next meaningful milestone.
More capital doesn’t automatically create a better company. ✨
Every extra dollar comes with dilution, expectations, and less control over what happens next.
Raise enough to reach the next meaningful milestone.
More capital doesn’t automatically create a better company. ✨
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