Return-Path: Delivered-To: andrew@sterlingcal.com Received: from reseller401.webserversystems.com by reseller401.webserversystems.com with LMTP id 4D7HD72iqGjL9AoAchKAPA (envelope-from ) for ; Fri, 22 Aug 2025 12:02:53 -0500 Return-path: Envelope-to: andrew@sterlingcal.com Delivery-date: Fri, 22 Aug 2025 12:02:53 -0500 Received: from o169.ptr1700.mail.beehiiv.com ([159.183.140.201]:19414) by reseller401.webserversystems.com with esmtps (TLS1.2) tls TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256 (Exim 4.98.1) (envelope-from ) id 1upVAC-000000032NU-23O9 for andrew@sterlingcal.com; Fri, 22 Aug 2025 12:02:53 -0500 DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=mail.beehiiv.com; h=content-type:date:from:mime-version:subject:reply-to:list-unsubscribe: list-unsubscribe-post:to:cc:content-type:date:from:subject:to; s=s1; bh=iUuc2BEkkDzCqfIQavV3qCTjx+b0hUwaVwS/pXaPrqU=; b=EmY+liRPXGcnHcx+sOA8eMycT5rdUy3M9TirhtfXEMk1om289gVc85CCk6R4MPF73AW6 8p5A4T3Q8Z9fZWtcIwbfmFbrMnB3k978u5fYAHVAkxaWEy0e/B6d6gNg8OTu/764QwiGiG dxWqyHzuMsChkZdeU3p2OAAySvG5x2F1w9RxWagPs4G6F+9HaPLEZslpGvc8e2mbVZKAtZ 9/EjheAwOtNxNi7f0oP0akbb/DSDZUC8FOP4G2G5FDqiZDTLr3Am2JUgduzriipdSnBhyI PprJoC7+y8cPzPGpE8w8KhOYgWg+m8v4pDTVLwCBAZtHzWb6TmIE7nDVg3vH7btw== Received: by recvd-549df64948-s5fpj with SMTP id recvd-549df64948-s5fpj-1-68A8A2A0-55 2025-08-22 17:02:24.176786184 +0000 UTC m=+6827325.174231297 Received: from NDAyMzQxODk (unknown) by geopod-ismtpd-27 (SG) with HTTP id -DQlRwTVSwW3D08OFsRvzg Fri, 22 Aug 2025 17:02:24.118 +0000 (UTC) Content-Type: multipart/alternative; boundary=70e4805a5632794a020ca6d837fda7d88bb1e06b395cfd4d7e613cad8037 Date: Fri, 22 Aug 2025 17:02:41 +0000 (UTC) From: Collin Stewart Mime-Version: 1.0 Message-ID: <-DQlRwTVSwW3D08OFsRvzg@geopod-ismtpd-27> Subject: Your 30-Minute Demo is Killing Deals Reply-To: Collin Stewart Feedback-ID: =?us-ascii?Q?dda96e45-874a-40fc-91bf-73b29f2de34c=3Anewsletter=3A3c5b97ff-00a9-?= =?us-ascii?Q?4acc-916d-c137bca24b1d=3A23270855726497d?= List-Unsubscribe: =?us-ascii?Q?=3Cmailto=3A3c5b97ff-00a9-4acc-916d-c137bca24b1d+1d17dc26-c1df-44e?= =?us-ascii?Q?0-812a-883b6ad5b6bc+dda96e45-874a-40fc-?= =?us-ascii?Q?91bf-73b29f2de34c=40unsub=2Ebeehiiv=2Ecom=3E=2C?= =?us-ascii?Q?_=3Chttps=3A=2F=2Ffoundersedition=2Eco=2Funsubscribe=2FeyJ0eXAiOiJKV1QiLCJhbG?= =?us-ascii?Q?ciOiJIUzI1NiJ9=2EeyJzdWJzY3JpYmVyX2lkIjoi?= =?us-ascii?Q?MWQxN2RjMjYtYzFkZi00NGUwLTgxMmEtODgzYjZ?= =?us-ascii?Q?hZDViNmJjIiwicG9zdF9pZCI6ImRkYTk2ZTQ1LT?= =?us-ascii?Q?g3NGEtNDBmYy05MWJmLTczYjI5ZjJkZTM0YyIsI?= =?us-ascii?Q?mxhc3RfcmVzb3VyY2VfZ3VpZCI6IlBvc3Q6ZGRh?= =?us-ascii?Q?OTZlNDUtODc0YS00MGZjLTkxYmYtNzNiMjlmMmR?= =?us-ascii?Q?lMzRjIn0=2E5szk=5F-=5FaqZ1-uM67MV5LRM3hUafVnI?= =?us-ascii?Q?t0noFo7rAkZlk=3E?= List-Unsubscribe-Post: List-Unsubscribe=One-Click sId: 3c5b97ff-00a9-4acc-916d-c137bca24b1d x-beehiiv-ids: =?us-ascii?Q?{=22account=5Fname=22=3A=22https=3A=2F=2Ffoundersedition=2Eco=2F=22=2C=22campaign=5Fid=22=3A=22d?= =?us-ascii?Q?da96e45-874a-40fc-91bf-73b29f2de34c=22=2C=22c?= =?us-ascii?Q?ategory=22=3A=22newsletter=22=2C=22email=5Fgenerated=5F?= =?us-ascii?Q?at=22=3A1755882144=2C=22user=5Fid=22=3A=223c5b97ff-00a9?= =?us-ascii?Q?-4acc-916d-c137bca24b1d=22}?= x-beehiiv-type: newsletter x-list-id: 3c5b97ff-00a9-4acc-916d-c137bca24b1d x-list-owner: x-newsletter: https://foundersedition.co/p/your-30-minute-demo-is-killing-deals x-newsletter-id: https://foundersedition.co/ x-newsletter-signup: https://foundersedition.co/subscribe X-SG-EID: =?us-ascii?Q?u001=2E7ozyt+tmjDsHnEocxX8pymFA2v5OOh2V4Pdr6hGVjZo99sLHT4OeEg7as?= =?us-ascii?Q?oEFtQzIa0qAOkk1QezFA4qrCcff9558yNK8x6zQ?= =?us-ascii?Q?0aLhxDCyAuB9kgcSLas3IIKR+fvCUJBBJPWt0aT?= =?us-ascii?Q?ilqs9wNn110q8Y0nUogkNtZmysvFy116gnOD86q?= =?us-ascii?Q?XOqSsfBPpYbM5+IInx8BH3i2DFr7XIxvKvqJKXR?= =?us-ascii?Q?2gwF=2F+I8I0bc5IKAK3wA9v2aaCLAi1H9VUuTr+p?= =?us-ascii?Q?Qotqtts9zFtrcfCYI9aYC7KzCE8DCy+6GSCNtX6?= =?us-ascii?Q?WLaGScUs=3D?= X-SG-ID: =?us-ascii?Q?u001=2ESdBcvi+Evd=2FbQef8eZF3BpTL9BgbK5wfSJMJGMsmprD1ZcmFObA4po1bG?= =?us-ascii?Q?aUE6gycJ+LfRoc8X0Wm0MSorFVcoWHrIixZYD9z?= =?us-ascii?Q?w25Z143eglkAJWbQrLxndYtch6lhNuMZAjzTdhS?= =?us-ascii?Q?+p7WkO424Ipk13O34SdX8bx0Vq1+NisSaeD1+e9?= =?us-ascii?Q?bxLW4qfw=2F6W5uTkds1sVwprngcf3y56tb+5pv6M?= =?us-ascii?Q?WS9YDZI+np72H7PX+tnSF6jdhY2ZdpJz6hlMLgI?= =?us-ascii?Q?9USK3pUPeany2oLBybnIMHZ+jEAtn9PY2uoQ=2FR7?= =?us-ascii?Q?QLZIEXOXib8ys+i=2FJItgjJbpSkn5At=2F6UpyvgEo?= =?us-ascii?Q?7kyI8q5IV4VrRqrsAjTZ0+sp=2FBl0cwfpscGPBwW?= =?us-ascii?Q?eVmTffeKQoO8BHL?= To: "andrew@sterlingcal.com" X-Entity-ID: u001.RuZ2+X9IBGtjUb8qq3teHQ== X-Spam-Status: No, score=-4.3 X-Spam-Score: -42 X-Spam-Bar: ---- X-Spam-Flag: NO --70e4805a5632794a020ca6d837fda7d88bb1e06b395cfd4d7e613cad8037 Content-Transfer-Encoding: quoted-printable Content-Type: text/plain; charset=utf-8 Mime-Version: 1.0 Hello Andrew,=20 **_Book update_**_: I just approved the Kindle version and found a solid ne= w audiobook producer (should be ready in 3 weeks). Initial sales projection= s just hit ~2,500 worldwide, including 300 from India where it's getting lo= cally produced and sold - which is honestly the most interesting part of th= is whole thing._ _If you haven't _[ordered already](https://www.amazon.com/Terrifying-Art-Fi= nding-Customers-Sleep-Deprived/dp/1774586134)_, you get a VC list, investor= list, and potentially a founder sales guide (see the last section for deta= ils) as a pre-order benefit. Just send me your receipt. _ _Anyway, back to your regularly scheduled sales advice..._ ## You're Not Getting Second Calls Because You Didn't Earn Them Most founders default to 30-minute discovery calls thinking shorter equals = easier to book. But here's what's actually happening: You're trying to cram= discovery, demo, and next steps into 30 minutes, which means you're either= rushing through discovery (so you don't understand the problem) or scrambl= ing to book the next call in the final 30 seconds while they're hitting "en= d meeting." The result? Pipeline quietly dies because you never built real momentum. Yo= ur 30-minute demo is killing your pipeline - and you don't even know it. ## The "Do Not Pass Go" Rule Just like in Monopoly - do not pass go, do not collect $200. Do NOT demo un= til you deeply understand their pain. The green light moment comes when you can say their problem back to them an= d they respond with "Exactly!" or "Yes, that's exactly what we're dealing w= ith." Only then do you demo. For example: "So if I understand correctly, yo= ur engineering team is spending 40% of their time on deployment issues, whi= ch is causing your product releases to slip by 2-3 weeks consistently, and = that's directly impacting your ability to hit Q4 revenue targets. Is that a= ccurate?" When they confirm with "Yes, exactly" - then you show them the 90= -second solution. The hard truth is that most founders are showing features, not how they can= solve the prospect's problems. Discovery isn't a checkbox to get to the de= mo - it's the most important part of the call. ## The Best Demos Are 90 Seconds Great demos last 30-90 seconds and answer one specific question. The formul= a is simple: "Based on what you just told me about [specific problem], let = me show you exactly how we solve that." Share screen, show the exact featur= e or workflow that addresses their pain, then explain: "This is how you'd g= o from [current bad state] to [desired good state] in about 30 seconds." You might have multiple of these 90-second clips, each one tied to a pain p= oint you found in discovery. Your demo should be closer to a TikTok video t= han a Lex Fridman podcast. If you truly understand their problem and can articulate how your software = solves it, what it looks like almost doesn't matter. The demo becomes proof= , not persuasion. The hard part isn't the demo - it's asking more questions= than feels comfortable, especially for first-time sellers. Most founders s= top asking questions too early because silence feels awkward. ## Stop Cramming Everything Into 30 Minutes Here's a better framework: 5-10 minutes for intros and agenda setting, 40 m= inutes for deep discovery (this is where deals are won or lost), 5 minutes = for targeted demo of only relevant parts, and 5 minutes for clear next step= s. Most founders think "30 minutes equals easier to book." Test this assumptio= n. Try asking for 45-60 minutes and see if people actually push back. You m= ight be surprised. Use honest positioning: "Typically these conversations t= ake about 45 minutes because I don't want to just show you everything and h= ope something sticks. I'd rather understand your specific challenges first = and show you exactly how we solve those. Does that work for your schedule?" If they push back, that's actually valuable information. If someone won't c= ommit 45 minutes to potentially solving a real business problem, they might= not be serious about solving it. When discovery comes first, your demo bec= omes proof of understanding, not a fishing expedition. ## Call Management Is Deal Management Sales calls are like reading sheet music - you need to know where you are i= n the song. Are you in the verse? The bridge? The solo? Every song ends, an= d you need to nail the ending. Psychology research shows people remember pe= ak emotions and ending emotions more than anything in the middle. A rushed = "sorry I gotta run" creates a negative ending memory that kills momentum. Start every call by asking: "I see we're scheduled for 30 minutes. Does eve= ryone have a hard stop at the top of the hour, or do we have some flexibili= ty?" This single question gives you crucial information without asking for = more time upfront. When you're 10 minutes from the end, check in: "I've got a couple more impo= rtant questions that typically take about 15 minutes. Do you all have a har= d stop, or can we continue for a few more minutes?" If they do have a hard = stop, pivot professionally: "No problem. Let me prioritize the most importa= nt questions, and we can schedule 30 minutes next week to dive deeper into = [specific area]." Pro tip: Always leave a 2-inch sliver on your monitor showing the time. Put= it right between your notes and their video. You can't manage what you can= 't see. End with confidence instead of scrambling to schedule in the last 3= 0 seconds: "Based on what we discussed, I think the next logical step is [s= pecific action]. I can send you times that work this week, or we can find s= omething right now. What works better for you?" ## You're the Expert in This Decision Process Here's the mindset shift you need: You're not just selling software - you'r= e the expert in how companies should evaluate and buy this type of solution= . You help teams make this decision every day. They do it maybe once every = few years. This expertise gives you the authority to guide the process. When a prospec= t says they only have 30 minutes, or they want to send materials to someone= else, or they need to "think about it" - you know from experience what usu= ally happens next. Most of the time, nothing happens. The evaluation stalls= , gets deprioritized, or they make a rushed decision they regret later. Your job isn't just to pitch your product. It's to help them follow a proce= ss that leads to the right outcome, whether that's buying from you or not. = When you approach sales calls with this expert mindset, you naturally becom= e more consultative and less desperate. You're not begging for their time -= you're investing your expertise in helping them solve a real problem. ## Don't Lose the Thread, Multi-Thread The next time a prospect wants to "show someone else," don't lose momentum = by forgetting to book a next step with the core decision makers. Use new en= trants as "in-between" calls. Respond with: "Great, I'm glad you're getting= [engineering/other stakeholders] involved. What we find is that [specific = role] typically cares about X and Y. Do you know what specifically matters = most to them?" If they can't answer, push for a live conversation: "I'd love to have a qui= ck 15-minute conversation with them to understand what they care about, so = I can make sure this is a good fit. Can you introduce us, or should I reach= out directly?" Use confident positioning: "You probably don't buy this type of software ve= ry often, but I help people make these decisions every day. Part of followi= ng a good process is getting all the right stakeholders involved early." Al= ways avoid "send me a demo video" requests. Materials can't answer question= s or handle objections. Always push for live conversations. ## Founder Sales Guide I'm considering putting together a Founder Sales Guide as my next project. = I haven't started yet because it's a lot of work. But after everyone floode= d my inbox for the mutual action plan template last week, I think it might = be worth doing. If you're interested, reply with "playbook." If you're really interested, r= eply with "playbook" plus a [receipt](https://www.amazon.com/Terrifying-Art= -Finding-Customers-Sleep-Deprived/dp/1774586134). The more interest there i= s, the more time I'll spend on it. Collin=C2=A0 PS - Stop asking for 30-minute calls, your solution is better than that. =E2=80=94=E2=80=94=E2=80=94 You are reading a plain text version of this post. For the best experience,= copy and paste this link in your browser to view the post online: https://foundersedition.co/p/your-30-minute-demo-is-killing-deals --70e4805a5632794a020ca6d837fda7d88bb1e06b395cfd4d7e613cad8037 Content-Transfer-Encoding: quoted-printable Content-Type: text/html; charset=iso-8859-1 Mime-Version: 1.0 Your 30-Minute Demo is Killing Deals
<= td align=3D"center" valign=3D"top" style=3D"border-width:0px 0px 0px 0px;bo= rder-style: solid; border-color: #FFFFFF;border-radius:10px 10px 0px 0px;ba= ckground-color:#FFFFFF;" class=3D"c">

August = 22, 2025   |   Read Online

Your 30-Minute Demo is Killing Deals

<= /tr>
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3D"share
 
= 3D"share
 
3D"share
3D""=
=

Hello = Andrew,

Book upd= ate: I just approv= ed the Kindle version and found a solid new audiobook producer (should be r= eady in 3 weeks). Initial sales projections just hit ~2,500 worldwide, incl= uding 300 from India where it's getting locally produced and sold - whi= ch is honestly the most interesting part of this whole thing.

If you haven't ordered already, you get a VC list, investor list, and potentially a fo= under sales guide (see the last section for details) as a pre-order benefit= . Just send me your receipt.

Anyway, back to your regularly scheduled sales advice...<= /span>

You're Not Getting Second Calls Because You Didn't Earn Them

Most founders default t= o 30-minute discovery calls thinking shorter equals easier to book. But her= e's what's actually happening: You're trying to cram discovery,= demo, and next steps into 30 minutes, which means you're either rushin= g through discovery (so you don't understand the problem) or scrambling= to book the next call in the final 30 seconds while they're hitting &q= uot;end meeting."

= The result? Pipeline quietly dies because you never built real momentum. Yo= ur 30-minute demo is killing your pipeline - and you don't even know it= .

The &= quot;Do Not Pass Go" Rule

Just like in Monopoly - do not pass go, do not collect $200. Do NO= T demo until you deeply understand their pain.

The green light moment comes when you can say their= problem back to them and they respond with "Exactly!" or "Y= es, that's exactly what we're dealing with." Only then do you = demo. For example: "So if I understand correctly, your engineering tea= m is spending 40% of their time on deployment issues, which is causing your= product releases to slip by 2-3 weeks consistently, and that's directl= y impacting your ability to hit Q4 revenue targets. Is that accurate?"= When they confirm with "Yes, exactly" - then you show them the 9= 0-second solution.

The= hard truth is that most founders are showing features, not how they can so= lve the prospect's problems. Discovery isn't a checkbox to get to t= he demo - it's the most important part of the call.

The Best Demos Are 9= 0 Seconds

Great demos = last 30-90 seconds and answer one specific question. The formula is simple:= "Based on what you just told me about [specific problem], let me show= you exactly how we solve that." Share screen, show the exact feature = or workflow that addresses their pain, then explain: "This is how you&= #39;d go from [current bad state] to [desired good state] in about 30 secon= ds."

You might hav= e multiple of these 90-second clips, each one tied to a pain point you foun= d in discovery. Your demo should be closer to a TikTok video than a Lex Fri= dman podcast.

If you tr= uly understand their problem and can articulate how your software solves it= , what it looks like almost doesn't matter. The demo becomes proof, not= persuasion. The hard part isn't the demo - it's asking more questi= ons than feels comfortable, especially for first-time sellers. Most founder= s stop asking questions too early because silence feels awkward.

=

Stop = Cramming Everything Into 30 Minutes

Here's a better framework: 5-10 minutes for intros and ag= enda setting, 40 minutes for deep discovery (this is where deals are won or= lost), 5 minutes for targeted demo of only relevant parts, and 5 minutes f= or clear next steps.

Mo= st founders think "30 minutes equals easier to book." Test this a= ssumption. Try asking for 45-60 minutes and see if people actually push bac= k. You might be surprised. Use honest positioning: "Typically these co= nversations take about 45 minutes because I don't want to just show you= everything and hope something sticks. I'd rather understand your speci= fic challenges first and show you exactly how we solve those. Does that wor= k for your schedule?"

If they push back, that's actually valuable information. If someo= ne won't commit 45 minutes to potentially solving a real business probl= em, they might not be serious about solving it. When discovery comes first,= your demo becomes proof of understanding, not a fishing expedition.=

Ca= ll Management Is Deal Management

Sales calls are like reading sheet music - you need to know wher= e you are in the song. Are you in the verse? The bridge? The solo? Every so= ng ends, and you need to nail the ending. Psychology research shows people = remember peak emotions and ending emotions more than anything in the middle= . A rushed "sorry I gotta run" creates a negative ending memory t= hat kills momentum.

Sta= rt every call by asking: "I see we're scheduled for 30 minutes. Do= es everyone have a hard stop at the top of the hour, or do we have some fle= xibility?" This single question gives you crucial information without = asking for more time upfront.

When you're 10 minutes from the end, check in: "I've go= t a couple more important questions that typically take about 15 minutes. D= o you all have a hard stop, or can we continue for a few more minutes?"= ; If they do have a hard stop, pivot professionally: "No problem. Let = me prioritize the most important questions, and we can schedule 30 minutes = next week to dive deeper into [specific area]."

Pro tip: Always leave a 2-inch sliver on your= monitor showing the time. Put it right between your notes and their video.= You can't manage what you can't see. End with confidence instead o= f scrambling to schedule in the last 30 seconds: "Based on what we dis= cussed, I think the next logical step is [specific action]. I can send you = times that work this week, or we can find something right now. What works b= etter for you?"

You're the Expert in This Decision Process<= /span>

Here's the mindset= shift you need: You're not just selling software - you're the expe= rt in how companies should evaluate and buy this type of solution. You help= teams make this decision every day. They do it maybe once every few years.=

This expertise gives y= ou the authority to guide the process. When a prospect says they only have = 30 minutes, or they want to send materials to someone else, or they need to= "think about it" - you know from experience what usually happens= next. Most of the time, nothing happens. The evaluation stalls, gets depri= oritized, or they make a rushed decision they regret later.

Your job isn't just to pitch your = product. It's to help them follow a process that leads to the right out= come, whether that's buying from you or not. When you approach sales ca= lls with this expert mindset, you naturally become more consultative and le= ss desperate. You're not begging for their time - you're investing = your expertise in helping them solve a real problem.

Don't Lose the = Thread, Multi-Thread

T= he next time a prospect wants to "show someone else," don't l= ose momentum by forgetting to book a next step with the core decision maker= s. Use new entrants as "in-between" calls. Respond with: "Gr= eat, I'm glad you're getting [engineering/other stakeholders] invol= ved. What we find is that [specific role] typically cares about X and Y. Do= you know what specifically matters most to them?"

If they can't answer, push for a live = conversation: "I'd love to have a quick 15-minute conversation wit= h them to understand what they care about, so I can make sure this is a goo= d fit. Can you introduce us, or should I reach out directly?"

Use confident positioning: &quo= t;You probably don't buy this type of software very often, but I help p= eople make these decisions every day. Part of following a good process is g= etting all the right stakeholders involved early." Always avoid "= send me a demo video" requests. Materials can't answer questions o= r handle objections. Always push for live conversations.

Founder Sales Guide

I'm considering putting tog= ether a Founder Sales Guide as my next project. I haven't started yet b= ecause it's a lot of work. But after everyone flooded my inbox for the = mutual action plan template last week, I think it might be worth doing.

If you're interested, = reply with "playbook." If you're really interested, reply wit= h "playbook" plus a receipt. The more interest there is, t= he more time I'll spend on it.

Collin=A0

P= S - Stop asking for 30-minute calls, your solution is better than that.

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