STARTING LINE

Mistakes. I've made a few, as I've learned over the past month.

I recently interviewed a founder for an article and had a list of questions for him. At one point, Scott referred to his fundraising as "professional begging." Did I stop running through my questions? Sadly, no. So I missed an opportunity for something special (more on that later).

If you've been interviewed for a podcast, profiled in a trade publication, or recorded a sales call this quarter, you're sitting on material your marketing team would kill for. Most of it never gets used. Not because it isn't there. Because nobody knows how to find it.

I built The Tape Room to fix that. It's a post-mortem framework for recorded interviews and conversations, much like how athletes review game film. I tested it on close to a dozen of my own transcripts before shipping it. If I had you at "Mistakes" (thanks, Jerry Maguire), you can download it here (no email required), and read the blog post here.

Here are a few things I've learned, pro and con:

THE GOOD:

1. The lie question. “What lie did you tell yourself for years that you finally stopped believing?” Three for three across recent interviews, including Scott's great story about advice from his dad and Maria's confession of parental guilt. It works because it bypasses the pitch and gets to the person. The best answers always have named characters, a specific moment, and something the subject has never said out loud before. This question may not work for you, but pay attention to the questions that do and make sure you always include them.

2. Constructive disagreement produced better material. When Paul implied there’s a male menopause equivalent, I pushed back: “There’s no such thing as male menopause.” That friction produced the andropause explanation, the testosterone decline data, and the clearest articulation of why midlife hits men as a shock rather than a known event. Agreeing would have gotten me a nod. Disagreeing got me the thesis.

3. The origin question that worked. “Tell me about the exact moment when this idea crossed the line from interesting to I have to build this, even if it’s messy and hard.” He proceeded to talk about travelers opening 15 tabs to compare flights, hotels, and activities, trying to figure out whether their Amex points transfer to this airline, and whether this hotel has a kids' club that takes a 4-year-old. All of it. On their own. On a Sunday night, when they should be relaxing. One specific, well-framed question did more work than six general ones.

4. Following the thread through multiple levels. Another client told me how he spent 18 months advising someone he hoped would eventually join him, including helping this potential competitor raise money. It came out because I asked follow-up questions at each stage. I didn’t accept the summary. That’s the interview working the way it’s supposed to.

THE NOT-SO-GOOD (BORDERING ON THE BAD)

1. "Professional Begging.” Scott dropped a vivid, specific phrase mid-answer about his fundraising, and the conversation moved forward without stopping. “Professional begging” is the kind of line that becomes a pull quote an editor circles. It’s more honest about fundraising than anything else he said on the topic. I needed to ask the follow-up: “Stop there. Professional begging: Is that really what it feels like? Walk me through what a day of that actually looks like. That phrase names something founders almost never say publicly: that fundraising is structurally humiliating for someone who once had authority and resources. It should have been a developed moment. Focus less on your list of questions and more on their answers.

2. Multi-part questions. This showed up across every one of my transcripts. A two-part question usually gets you the answer to whichever half your subject or client feels safer with. A three-part question gets you the one the subject felt most comfortable giving. The other answers disappear. One question at a time, every time. There's a related observation here: My questions are often VERY long and rambling, even with the notes I put on top of my questions -- SLOW DOWN! and KEEP IT SHORT.

3. The origin story that dissolved. When a different Paul told me he left school early and ran a desk out of his father’s professional office. Mid-sentence, he lost the thread and asked me to repeat the question. I gave him the original instead of saying “stay where you were.” A founder who left school to work out of his father’s firm is a better origin story than almost anything else in that transcript. It’s still sitting in the almost.

4. Talking about yourself at the wrong moment. A different Paul said his podcast “just took off,” and he started getting messages from older men like him. That first one came from a man who had never told anyone he was struggling. That's the reason Paul's podcast exists. My response was to spend two minutes talking about losing my own father and the sudden nature of his death. The empathy was real. The timing cost me the material. I should have asked him to "Tell Me More" about that listener's email.

If you want to run The Tape Room on your own recordings, download it here. No email required.

If you'd rather have someone do it with you, I can help. I sit with founders and executives, listen to their recorded conversations (sales calls, board prep, podcast appearances, internal town halls, short- or long-form content), and pull out the moments that their next LinkedIn post, investor letter, or About page should be built around. Reply to this email, and we'll set up a call.

FOR YOUR CONSIDERATION

1. What are the trickier positioning roadblocks out there, and how can teams get around them? April Dunford did a deep dive on this topic for Lenny's Newsletter. It's long, but it's terrific (as all her content is). Learn more: A Guide to Advanced B2B Positioning.

2. Amanda Natividad says, "In a zero-click world, content has to do more than earn visits. It has to create understanding, trust, recall, and demand." Learn more in "It's Not a Content Marketing Problem. It's a Business Problem."​

3. Andy Crestodina's posts are well-written and actionable. What more can you say? In this post, he says most weak web pages have the same problem: They're not specific enough. This article includes a simple prompt to audit any page for specificity. It took five minutes to run on Claude and 15 minutes to make the first few changes.

HOW CAN I HELP?

I've been working on ways to help people optimize their LinkedIn profiles, with a recent focus on how the algorithm evaluates their profiles and content. The output will help those who want to do it themselves, but I'm also here if you need help either on a one-time basis (fix my profile) or an ongoing basis (help with posts and/or longer-form content. If you're a B2B founder or a financial services executive who suspects your LinkedIn presence isn't quite on-brand, I'll do a one-time audit at no cost. First 10 only.

I welcome your comments or suggestions for future issues. Drop me a note here. If you found this on LinkedIn or had it forwarded to you, you can subscribe by clicking the button below.