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The Device Files: From Concept to Commercialization · Aug 5, 2026

Burn the Haystack: Understanding the Investor Mindset, Part Two

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The Ick Factor

The Burned Haystack Dating Method was created by Dr. Jennie Young, professor of writing and rhetoric at the University of Wisconsin-Green Bay. This series is not affiliated with or endorsed by Dr. Young or the Burned Haystack Dating Method. It is an independent application of her analytical approach to founder-investor dynamics, with full credit to her original work.

Last week I walked through the methodology of the Burn the Haystack movement and how it maps to understanding the mindset of an investor. If you missed it, here you go:

This week we’re delving into the second half of Young’s framework, which is the rhetorical analysis examples you can use to weed out bad dating prospects – or in our case, what things give our investors the “ick”.

This article would not have been possible without the great conversations I had with the following people who helped me shape this piece with real-world examples: Alberto Chan, Scott Walchek, Ben Patterson, Javier Perez, Jakob Diepenbrock, Diane Bouis, Amy Millman, Jackson Streeter, and Mihir Patel.

Yeah, this article took a lot of work, so I hope you appreciate it 😊

The Device Files: From Concept to Commercialization is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

Critical Rhetoric Analysis

In Burn the Haystack, Dr. Young gives us a lot of good patterns we can look out for, or just use to put words to the unnamed reasons some profile gave us the “ick”. The concept of Critical Rhetoric Analysis has been around for a while. Its about what we learn by reading between the lines to understand what’s implied.

Here are two examples to give you an idea of how it works:

  1. The “Test and Apologize”. This is a guy who sends something sexual then preemptively apologizes for being too forward. Why do we care? Well besides the fact that it was kinda creepy, he’s actually using it to test what he can get away with. The apology purposefully puts you in an awkward position where you either just put up with it because he apologized and so everything is cool now, right? Or you say it wasn’t cool, and now you’re meant to come across as not being able to take a joke.

  2. The “My Kids Come First”. This guy is a tricky one. Having your kids come first sounds really sweet at first blush, so why did it give you pause? Well because actually he’s just created an unnecessary pecking order and letting you know you’re not on the top, you’re probably never going to be close to it, and that should keep you in your place.

If you’re a guy reading this and thinking this is all too nitpicky, you may be “that guy”. But I’m not here to debate her method, I’m here to make our own list! So, here’s The Device Files list of Rhetorical Red Flags when trying to get investor attention.

Rhetorical Red Flags

We’re not going to spend a lot of time digging into the details on each of these, because actually there are quite a few - and really they aren’t that hard to understand (unlike that Kids Come First one. That’s tricky stuff).

1. The Resume Open

The founder who opens the pitch with credentials instead of the reason for building. Bragging that you went to Harvard plays the same way with investors as it does in dating. Some people will be impressed. Others will get the ick. The founder who opens with pedigree is telling the investor they think their pedigree substitutes for a thesis. Your education isn’t a replacement for having the right solution to a real problem, but it might signal you have the right connections. Play that hand carefully.

2. The Cookie Cutter Pitch

The deck that clearly followed a “10 things to include in your pitch” template. Problem slide, solution slide, market size, team, traction, ask, in the same order every founder learned in the same accelerator. The problem here is that:

  1. It looks like you asked AI to create your deck and didn’t think it through yourself

  2. Its most likely not telling a compelling narrative. To have a truly good pitch you need to grab an investor’s attention and tell a story compelling enough that they want to know how it ends.

On dating apps this would be the guy who asks some lame question they read was the best way to start a conversation in the advice columns. Like, “Hey. How’s your day going?”

3. The Sloppy Show-Up

The founder who shows up unprepared. Untied shoes. Wrinkled shirt. Typos in the deck. Numbers that don’t add up between slides.

To be clear, you don’t have to be in a three piece suit. You can show up looking like an investment banker, and IBM exec, or the Silicon Valley jeans, sneakers, t-shirt look. But they all do it with polish. What’s not fine is showing up looking like you couldn’t be bothered. It’s the same as dating. Did you shower? Put on deodorant? Founders who can’t get it together are telling the investor how they’re going to run the business.

4. The Trophy Collector

The founder who’s stacked up pitch competition wins, accelerator badges, and startup awards, and puts all of them on the deck. Who talks proudly about winning the elevator pitch competition at some conference. Who’s optimized for the appearance of success. Some investors see accumulated pitch-competition wins as a red flag, because it signals the founder has been spending their time performing instead of building the company. The dating parallel is the guy who’s very proud of notches in his bedpost. Somewhere along the way he mistook game for the real thing.

Which leads us to the next one…

5. The Pickup Artist

Remember The Game? Negging? The “tools of the pickup artist”? Well, the same goes for using obvious and outdated sales techniques. The founder who uses your name too much. Who feels like he’s closing you constantly instead of talking to you.

Some people fall for the sales-guy thing. Some people get the ick from it. That’s fair. Not every pattern in this piece is the same ick for everybody. But the founder whose skill set is a heavily-calibrated sales technique is going to hit that ick with a real percentage of the investors they meet, and the investors who read them as slick are often (or hopefully?) the sophisticated ones the founder wants.

6. The Fantasy Founder

This one is particularly fun because it directly parallels one in Dr. Young’s book. Guys who have a fantasy woman in their head that no real woman could live up to. They say in their profile they’re “Looking for a woman who loves to dress up but is just as happy hanging out in sweats with no makeup. Someone who can hold her own at a black-tie gala AND wants to camp under the stars. Loves the opera but also a dive bar. Down to earth, but ambitious. Adventurous, but a homebody. Independent, but loves to cuddle. Fit, but loves pizza. You get the idea.” You can have high standards but we’re also real people and not Build-a-Bears.

In the startup world this is the founder who has built a beautiful model of how the world will respond to their company, and the model bears (no pun intended) no relationship to how the real world actually works. This shows up in multiple ways:

· The hockey stick that goes up and to the right in a straight line for eight straight years.

· The $100 billion TAM with the “and we only need 1%” line - as if 1% of a huge market were a strategy rather than a wish.

· The “we have no competition” slide, which either means the founder doesn’t know or understand the competition.

· The projections built on assumed infection rates or usage frequencies that a sophisticated reader knows are wrong.

7. The Un-Coachable

The founder who takes any pushback as an attack. When the investor asks a follow-up question that implies they know something the founder doesn’t, the un-coachable founder digs in on their original answer instead of picking up the hint. This is the dating equivalent of the guy whose girlfriend has told him five times to pick his laundry up off the bedroom floor and yet, there is still is and he’s offended she keeps nagging him about it.

No investor wants to think the leader they’re investing in is uncoachable. It’s a hard balance to hit – accepting new ideas while still having conviction. Especially if you’ve already considered those points. I personally think this is one of the greatest skills a founder can learn, and one of the hardest.

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8. The Fake Insider

The founder who claims connections, traction, or validation that don’t survive scrutiny. Investments from foreign HNWI (High Net Worth Individual) that never materialize, a list of advisors who don’t actually remember speaking to the company, or future commitments for sales that are a real stretch given they just had a vague response from a mid-level manager. Sometimes its stating regulatory certainty about an FDA pathway they have never discussed with the agency.

Its pretty simple – don’t fabricate stuff. Just be honest about where you are and the help you could use to get to your next milestones.

9. The Self-Deluded

The founder who insists they’re not the kind of company they clearly are. This is usually attached to something that is a current buzzword or a market they think comes with a higher valuation – or they’re just ignorant because they’re trying to play in a space they have no experience in.

Examples: The SaMD company that thinks they don’t need to be talking to medical device investors because, “It’s not a medical device - it’s ‘AI software’”. Think of some buzzwords that have popped up in the last few years “AI” “blockchain” “digital twin” “BCI”. Not that there aren’t completely legitimate companies in these categories, but is YOUR company in that category?

The dating parallel is the guy whose self-image doesn’t match reality, like he tells you he’s a low-drama guy but always seems to attract crazy women. He isn’t lying, exactly. He genuinely believes his self-description. The problem is that his self-description isn’t accurate.

10. The Cool Kids Club

The founder who ranks people by perceived importance and treats them accordingly. He ignores you at the conference until he finds out you know someone important, and then he suddenly wants your card. He’s dismissive of the woman at the booth until he realizes she’s a partner at the fund. Then all of a sudden, he’s warm and inclusive and inviting you to the private dinner.

We all know the dating rule about seeing how people “treat the help”. This one is totally basic and isn’t one you can fix. As my dad always says, “Sooner or later everyone sees the cut of their jib.”

11. The Know-It-All

The founder who thinks he’s hot shit and doesn’t know what he doesn’t know. Doesn’t hire specialists because he thinks he can figure it out. Did his own pre-sub with the FDA without a regulatory consultant (BTW if you’re this guy – EVERYONE is worried you messed that up and have no clue what damage you might have already done). Dismisses market access, reimbursement strategy, or clinical study design as things he’ll get to later.

The dating parallel is the guy who won’t ask for directions, won’t read the instructions, and won’t take advice from anyone who might have been through what he’s about to walk into. He’ll figure it out, he always does! Except when he doesn’t.

12. The Dreamer

The founder with big vision and no plan. They can tell you a great story about where they’re going but can’t give you any good details on how they plan to get from here to there quarter by quarter.

Also in this category – the guy who just can’t seem to figure out how to find investors. Guess what? That’s your job as CEO. If you can’t figure it out, you’re not destined to be the CEO of a successful business. So, either figure it out or get yourself a real CEO.

The dating parallel is the guy who’s always about to. About to start the business, get in shape, propose, or fix that thing on the ‘Honey-do’ list. The vision is always bigger than the execution.

13. The Won’t Take a Hint Guy

The founder who follows the investor into the bathroom to keep pitching (yes, these are REAL examples), inserts himself awkwardly into a conversation without an introduction, or who sends five unanswered follow-up emails. Every version of this is the same underlying failure to read the room. The dating parallel is the guy who won’t leave you alone at the bar after you’ve made it clear you’re not interested. And why do investors run away? Because that inability to read the signal and adjust is going to show up in other aspects of the company’s success, like in how you deal with potential customers or your employees.

The Point of the List

There’s an ongoing conversation in the Burned Haystack community about whether men should even get feedback on their profiles. In the dating world, the general consensus is that we shouldn’t give feedback, lest we arm bad dating prosects with cheat codes that allow them to mask their true intentions.

However, I believe in the world of entrepreneurship most of these issues can be overcome with a good team or the right training – and if not, we’ll probably figure you out anyway! But I wanted to mention this because the goal here isn’t to become better at hiding a bad company behind good investor communication (we don’t want another Theranos, thank you).

If your pitch is signaling something is off, the issue is almost never the phrasing. There is something not fully thought through, or a misconception about what the investor actually needs to hear, or a real fundamental that has not been nailed down. This list is to help entrepreneurs figure out where they might need to do some real work.

That, and it was kinda fun to make.

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The Good News

The good news is, if you managed to not make any of these faux pas then you most likely fall into the category of a “needle”. You’ve now become one of the very select few worth talking to. You might not be THIS investor’s needle in the haystack, but you’re probably someone’s – so keep getting out there!

Next week we’re going to wrap up the series by talking about what works.

Blythe Karow is a strategic management consultant and founder of The Karow Advisory Group. The insights shared here reflect Blythe’s strategic expertise navigating the complex world of MedTech and wearables. Imagine what that same thinking could uncover when applied to your business.

How Blythe can help:

  • Commercialization & Market Readiness Reviews

  • Product & Business Strategy

  • U.S. Market Entry Planning & Education

  • Strategic Advisory for MedTech, Wearables, and HealthTech

Read on blythekarow.substack.com

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