Return-Path: Delivered-To: andrew@sterlingcal.com Received: from reseller401.webserversystems.com by reseller401.webserversystems.com with LMTP id 8D2FKdtDcWhDDwsAchKAPA (envelope-from ) for ; Fri, 11 Jul 2025 12:03:23 -0500 Return-path: Envelope-to: andrew@sterlingcal.com Delivery-date: Fri, 11 Jul 2025 12:03:23 -0500 Received: from o170.ptr9231.mail.beehiiv.com ([159.183.140.172]:11106) by reseller401.webserversystems.com with esmtps (TLS1.2) tls TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256 (Exim 4.98.1) (envelope-from ) id 1uaH9e-000000034C3-3sgM for andrew@sterlingcal.com; Fri, 11 Jul 2025 12:03:23 -0500 DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=mail.beehiiv.com; h=content-type:from:mime-version:subject:reply-to:list-unsubscribe: list-unsubscribe-post:to:cc:content-type:from:subject:to; s=s1; bh=vIwVIcQbQm+22j/LGcg/2zGEjv3fCUlfXVbTxrNL5l0=; b=IJ429zEqiruLLt2vcspvNhENNb3Tz3qIkMryDf5JuCHOXbGqaqwrFroRXLMsZnzLcIR0 o2IEskLdvH9Slpv/QRsVHcP/g3wGXL98KuoJK1SqBgS3JS+ppXoSC+qE87qVGak/d/grib DcRN1JOGX0wr9+Dwo296po8wAJHa93jwDkbiz9MkhpqZvDR872idgOIj0+M6T0nBMTrTNm AHkNcQY7n681/0qDFfW7upz/Dzet98uGmniM7Y1d0tfdS2idwuAfzTgMtsOQPfAo2GQDPr zepCoGV4JNcGoXmJv+B8F0ADyKV4M/iI5DB1sfuOUOpQHgBaYHuSwBHhZSuxAzUA== Received: by recvd-695b55cd4d-gcvxf with SMTP id recvd-695b55cd4d-gcvxf-1-687143A6-54 2025-07-11 17:02:30.154126075 +0000 UTC m=+3197880.356519826 Received: from NDAyMzQxODk (unknown) by geopod-ismtpd-0 (SG) with HTTP id w_xz33klSvCfdPqjsiItZw Fri, 11 Jul 2025 17:02:30.026 +0000 (UTC) Content-Type: multipart/alternative; boundary=7bf28879d092e84e44e108f74764eb0b6f805d55d1fae120bdfdb9a6818e Date: Fri, 11 Jul 2025 17:03:11 +0000 (UTC) From: Collin Stewart Mime-Version: 1.0 Message-ID: Subject: Trust your gut Reply-To: Collin Stewart Feedback-ID: =?us-ascii?Q?04df61c4-d7fc-4ca4-93cb-8c1e8220cd20=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+04df61c4-d7fc-4ca4-?= =?us-ascii?Q?93cb-8c1e8220cd20=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?hZDViNmJjIiwicG9zdF9pZCI6IjA0ZGY2MWM0LW?= =?us-ascii?Q?Q3ZmMtNGNhNC05M2NiLThjMWU4MjIwY2QyMCIsI?= =?us-ascii?Q?mxhc3RfcmVzb3VyY2VfZ3VpZCI6IlBvc3Q6MDRk?= =?us-ascii?Q?ZjYxYzQtZDdmYy00Y2E0LTkzY2ItOGMxZTgyMjB?= =?us-ascii?Q?jZDIwIn0=2EAJ8jGWmNuUkJnXTr=5FuONZ-=5FSyu8-1I?= =?us-ascii?Q?4H0exLFjfzHdk=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=220?= =?us-ascii?Q?4df61c4-d7fc-4ca4-93cb-8c1e8220cd20=22=2C=22c?= =?us-ascii?Q?ategory=22=3A=22newsletter=22=2C=22email=5Fgenerated=5F?= =?us-ascii?Q?at=22=3A1752253349=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/trust-your-gut 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+fvCUJBBhexKzam?= =?us-ascii?Q?f8+fZZe+DYqvepESOMEUsCkHHFpTzvzgRJCkbaQ?= =?us-ascii?Q?4D=2FvZjG7seX+ghxxRLasaqtU3mrI7kOkE9qP8D=2F?= =?us-ascii?Q?ekhHbfmYKS+3Eod57txa7fxW14BrUBPnOw9EXEd?= =?us-ascii?Q?3Y7Q668+lYEwFxHt=2Fdw5=2FhOQJN3fjz2wG+KuNS3?= =?us-ascii?Q?Le=2FSkqU0=3D?= X-SG-ID: =?us-ascii?Q?u001=2ESdBcvi+Evd=2FbQef8eZF3BpTL9BgbK5wfSJMJGMsmprD1ZcmFObA4po1bG?= =?us-ascii?Q?aUE6gycJ+LfRoc8X0Wm0MSorFVcoWHrIixZYD9z?= =?us-ascii?Q?w25Z143eglkAJWbQrLxndYtch6lhNuMZlJvnWcK?= =?us-ascii?Q?B6cVlkwX+=2FO699QxZkVwiCRofIDqcd=2F36CzRa4C?= =?us-ascii?Q?dfzka+e=2FwEH6=2FDW++5SoAm6sXqnmX3LgTBoVWWF?= =?us-ascii?Q?CyotcAICp+oe4fCJ5l=2FRok+MFTN+P6ee4EIJtUS?= =?us-ascii?Q?i2eW63=2Fb+eXNfzVu5rL14DnCBDpXmEQ8wO8UbMZ?= =?us-ascii?Q?QAsVqMGDuNityUMEAyYoL=2FCCrbCjFuSCKtRu66w?= =?us-ascii?Q?uv1YeTqwKZ+WCtDrUhqptPPwBGo+fH+Hw=3D?= To: "andrew@sterlingcal.com" X-Entity-ID: u001.RuZ2+X9IBGtjUb8qq3teHQ== X-Spam-Status: No, score=-0.3 X-Spam-Score: -2 X-Spam-Bar: / X-Spam-Flag: NO --7bf28879d092e84e44e108f74764eb0b6f805d55d1fae120bdfdb9a6818e Content-Transfer-Encoding: quoted-printable Content-Type: text/plain; charset=utf-8 Mime-Version: 1.0 Hello Andrew,=20 _**Book Update**__ - I just spent two days locked in a recording studio nar= rating the audiobook! It went well, but holy hell was it exhausting - turns= out reading your own book aloud for 9 hours straight is harder than writin= g it. _[Pre-orders](https://www.amazon.com/Terrifying-Art-Finding-Customers= -Sleep-Deprived/dp/1774586134)_ are live, and I'm putting together a workbo= ok that walks you through the entire playbook step-by-step. This guide is e= xclusive to pre-order folks and you'll get it before the book releases. Gra= b your copy, send me the receipt, and I'll add you to the VIP list._ _**An experiment**__ - I tried something different this week, instead of si= tting down and writing, I wrote an outline on a post-it, recorded it, and t= hen used the transcript as my initial first draft of the newsletter. You ca= n check out _[_the video_](https://youtu.be/3QdwdR8_SCk)_ here. Let me know= if you like this style._ Thirteen years into this entrepreneurial roller coaster, I've learned somet= hing crucial: the very instinct that made you crazy enough to start a compa= ny is probably the same one you've been systematically trained to ignore. Think about it. You had the conviction to quit a six-figure job and go to z= ero income. You believed something so deeply that you were willing to bet e= verything on changing how people use CRM, or prospect, or whatever big prob= lem you're tackling. That takes a special kind of insanity - the good kind. But here's what happened to me, and I suspect it's happening to you too. ## The Slow Erosion of Founder Conviction As I built out our team and hired smart executives, I started doing what al= l the mentors told me to do: "mature," "grow up," "become a professional CE= O." I began deferring to other people's expertise and trusting myself less. Every time we had a strategic decision, I'd weigh my gut instinct equally w= ith everyone else's opinion. I believed in flat organizational structures a= nd collaborative decision-making. Sounds smart, right? Wrong. What actually happened was my reliance on intuition - the thing that made m= e successful in the first place - dropped precipitously. I went from founde= r mode to professional manager mode, and it killed my company's momentum. The result? More than a couple of years where I genuinely didn't love runni= ng Predictable Revenue. We had good people and good customers, but I wasn't= happy. I didn't have high enough conviction to break through the inertia o= f "this is how we've always done it." ## The Confidence Roller Coaster Every founder experiences this. Even [Sam Altman](https://blog.samaltman.co= m/the-days-are-long-but-the-decades-are-short) (see rule 36, =E2=80=9Cthe d= ays are long but decades are short=E2=80=9D) has days where he feels like t= he king of the world and days where everything seems ready to explode. You'= re not alone in having these swings between supreme confidence and riding t= he struggle bus all the way home. The problem isn't the ups and downs - those are inevitable. The problem is = when low confidence leads you to stop trusting the very instincts that got = you here. ## Two Books That Changed Everything When I was struggling to find my strategic footing, two books completely tr= ansformed how I think about decision-making: **Good Strategy, Bad Strategy** by Richard Rumelt showed me I'd never actua= lly done anything strategic. All our quarterly planning and annual goal-set= ting were just "pick a number and make up math to get there." We had fancy = names and big hairy audacious goals, but zero strategic thinking. Rumelt's framework is deceptively simple: * **Situation**: What's actually happening? What position are you in? * **Diagnosis**: Why are you in this situation? What's the real crux? * **Guiding Policy**: How will you get out of this situation? * **Coherent Action**: What are the specific next steps? This isn't something you can rush through. The last time I ran this with my= exec team, we spent nearly an entire day just on situation and diagnosis. = But that deep thinking revealed strategic blind spots I'd been missing for = years. **How to Decide** by Annie Duke (yes, the poker player) taught me about dec= ision quality versus outcomes. You can make great decisions and still have = bad outcomes - that doesn't make you a bad founder. Duke's insight hit me like a ton of bricks: she didn't want to be an "outco= mes collector." She wanted to follow a good decision process. When she play= ed a poker hand correctly but lost, she was still a good poker player. The same applies to you. Your last sale, your last customer interaction, yo= ur last product launch - none of these individual outcomes define whether y= ou're a good entrepreneur. ## From Beliefs to Bets Here's the game-changer from Duke's approach: when you write down your assu= mptions, biases, and probabilities, they transform from beliefs into bets. = Beliefs are internal and hard to challenge. Bets are measurable and testabl= e. Her six-step process centers on building a living decision tree using what = she calls the 3 Ps - Preferences, Payoffs & Probabilities: 1. **List possible outcomes** - Sketch a "decision multiverse" showing ever= y branch that could unfold 2. **State your preferences** - Attach what you value (money, time, reputat= ion, happiness) to each branch so trade-offs are explicit 3. **Estimate probabilities** - Make your best guess for how likely each ou= tcome is, using both inside knowledge and outside base-rates 4. **Compare upside vs. downside** - Ask whether the reward justifies the r= isk; get precise where it matters, stay loose where it doesn't 5. **Iterate & expand** - Loop back through steps 1-4 for unexplored option= s or when new information arrives 6. **Commit, then check** - If no single piece of additional data would cha= nge your decision, decide, document why, and move on When you combine this with Rumelt's strategic thinking, you get something p= owerful: a framework for trusting your gut while making high-quality decisi= ons. ## Why This Matters Now I'm not telling you to ignore your team or make unilateral decisions. I'm t= elling you to remember that you're the expert on your customers and your ma= rket. You've done the work. You understand the gap you're trying to fill. Where I failed was communicating my instincts to the team in a way they cou= ld understand and get behind. I let imposter syndrome convince me that ever= yone else's opinion was as valuable as mine on core strategic questions. That's not true. As the founder, you have context and conviction that other= s simply don't have. Your job isn't to be democratic about vision - it's to= be right about where you're going and compelling about why others should f= ollow. ## The Turnaround Six months ago, I made the scary decision to shut down our outsourcing busi= ness and pivot to coaching founders. It was terrifying, but following this = strategic framework gave me the conviction to push through the inertia. The result? I'm 10x happier running my company today than I was a year ago.= The team pulled through, and we're building something I genuinely love aga= in. ## Your Next Move Here's what I want you to do: 1. Buy these books. Seriously. Good Strategy, Bad Strategy and How to Decid= e will change how you think about running your company. 2. Document your biases. Write down what you believe about your market, you= r customers, your competition. Transform those beliefs into testable bets. 3. Run the strategy framework. Spend serious time on situation and diagnosi= s. Don't rush to solutions. 4. Trust your gut, but verify it. Your instincts got you here. Don't let th= em be drowned out by committee thinking. You started this company because you saw something others didn't. That visi= on, that conviction, that willingness to make big bets - those are features= , not bugs. The market needs founders who trust themselves enough to make bold moves. Y= our customers need you to have conviction about where you're taking them. So trust your gut. But make it strategic. You've got this. _What's your experience with balancing gut instinct and strategic thinking?= Hit reply and let me know - I read every response._ Collin=C2=A0 PS - I=E2=80=99d love your feedback on what else I can create for you all a= s a reward for pre-ordering the book. Here are a few ideas: exclusive pre-o= rder book club, video course to accompany the workbook, a physical copy of = the workbook (madlibs style), and access to a GPT with the full content of = the book. Hit reply and let me know.=20 PPS - if you love audiobooks and can commit to a quick turnaround, I=E2=80= =99m looking for a few people to listen and help me find any issues. Hit re= ply if you=E2=80=99re interested.=C2=A0 =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/trust-your-gut --7bf28879d092e84e44e108f74764eb0b6f805d55d1fae120bdfdb9a6818e Content-Transfer-Encoding: quoted-printable Content-Type: text/html; charset=utf-8 Mime-Version: 1.0 Trust your gut
=
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July 11= , 2025   |   Read Online

Trust y= our gut

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=3D"share
 
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<= /tr>=

H= ello Andrew,

Book Update - I just spent two days locked in a recording studio narrating the a= udiobook! It went well, but holy hell was it exhausting - turns out reading= your own book aloud for 9 hours straight is harder than writing it. Pre-orders are live, and I'm pu= tting together a workbook that walks you through the entire playbook step-b= y-step. This guide is exclusive to pre-order folks and you'll get it be= fore the book releases. Grab your copy, send me the receipt, and I'll a= dd you to the VIP list.

An experiment - I tried something different this week, instead of sitting down an= d writing, I wrote an outline on a post-it, recorded it, and then used the = transcript as my initial first draft of the newsletter. You can check out <= /i>the video here. Let me know if you like t= his style.

Thirteen= years into this entrepreneurial roller coaster, I've learned something= crucial: the very instinct that made you crazy enough to start a company i= s probably the same one you've been systematically trained to ignore.

Think about it. You had = the conviction to quit a six-figure job and go to zero income. You believed= something so deeply that you were willing to bet everything on changing ho= w people use CRM, or prospect, or whatever big problem you're tackling.= That takes a special kind of insanity - the good kind.

But here's what happened to me, and I = suspect it's happening to you too.

The Slow Erosion of Founder Con= viction

As I built out= our team and hired smart executives, I started doing what all the mentors = told me to do: "mature," "grow up," "become a prof= essional CEO." I began deferring to other people's expertise and t= rusting myself less.

Ev= ery time we had a strategic decision, I'd weigh my gut instinct equally= with everyone else's opinion. I believed in flat organizational struct= ures and collaborative decision-making. Sounds smart, right?

<= span style=3D"color:rgb(44, 62, 80);">Wrong.

What actually happened was my reliance on intuition -= the thing that made me successful in the first place - dropped precipitous= ly. I went from founder mode to professional manager mode, and it killed my= company's momentum.

The Confi= dence Roller Coaster

E= very founder experiences this. Even Sam Altman (see rule = 36, =E2=80=9Cthe days are long but decades are short=E2=80=9D) has days whe= re he feels like the king of the world and days where everything seems read= y to explode. You're not alone in having these swings between supreme c= onfidence and riding the struggle bus all the way home.

The problem isn't the ups and downs - = those are inevitable. The problem is when low confidence leads you to stop = trusting the very instincts that got you here.

Two Books That Changed Ev= erything

When I was st= ruggling to find my strategic footing, two books completely transformed how= I think about decision-making:

Good Strategy, Bad Strategy by Richard Rumelt showed me I'd never ac= tually done anything strategic. All our quarterly planning and annual goal-= setting were just "pick a number and make up math to get there." = We had fancy names and big hairy audacious goals, but zero strategic thinki= ng.

Rumelt's framew= ork is deceptively simple:

  • Situation: What's ac= tually happening? What position are you in?

  • Diagnosis: W= hy are you in this situation? What's the real crux?

  • Guiding Policy: How will you get out of this situation?

  • Coherent Action: What are the specific next steps?

This isn't something you ca= n rush through. The last time I ran this with my exec team, we spent nearly= an entire day just on situation and diagnosis. But that deep thinking reve= aled strategic blind spots I'd been missing for years.

How to Decide by Annie Duke (yes, the poker p= layer) taught me about decision quality versus outcomes. You can make great= decisions and still have bad outcomes - that doesn't make you a bad fo= under.

Duke's insig= ht hit me like a ton of bricks: she didn't want to be an "outcomes= collector." She wanted to follow a good decision process. When she pl= ayed a poker hand correctly but lost, she was still a good poker player.

The same applies to you. = Your last sale, your last customer interaction, your last product launch - = none of these individual outcomes define whether you're a good entrepre= neur.

From= Beliefs to Bets

Her= e's the game-changer from Duke's approach: when you write down your= assumptions, biases, and probabilities, they transform from beliefs into b= ets. Beliefs are internal and hard to challenge. Bets are measurable and te= stable.

Her six-step pr= ocess centers on building a living decision tree using what she calls the 3= Ps - Preferences, Payoffs & Probabilities:

  1. List possible outcomes - Sketch a "decision mult= iverse" showing every branch that could unfold

  2. State your preferences - Attach what you value (money, time, reputation, happin= ess) to each branch so trade-offs are explicit

  3. Estimate probabilities - Make your best guess for how likely each outcome is, using = both inside knowledge and outside base-rates

  4. Compare upside vs. downside - Ask whether the reward justifies the risk; get precise w= here it matters, stay loose where it doesn't

  5. Iterate & expand - Loop back through steps 1-4 for unexplored options or when ne= w information arrives

  6. Commit, t= hen check - If no single = piece of additional data would change your decision, decide, document why, = and move on

When you combine this with Rumelt's strategic thinking, you get s= omething powerful: a framework for trusting your gut while making high-qual= ity decisions.

Why This Matters Now

I'm not telling you to ignore your team or make unilateral decisi= ons. I'm telling you to remember that you're the expert on your cus= tomers and your market. You've done the work. You understand the gap yo= u're trying to fill.

That's not true= . As the founder, you have context and conviction that others simply don= 9;t have. Your job isn't to be democratic about vision - it's to be= right about where you're going and compelling about why others should = follow.

The Turn= around

Six months ago,= I made the scary decision to shut down our outsourcing business and pivot = to coaching founders. It was terrifying, but following this strategic frame= work gave me the conviction to push through the inertia.

The result? I'm 10x happier running m= y company today than I was a year ago. The team pulled through, and we'= re building something I genuinely love again.

Your Next Move

Here's what I want you to do:

  1. Buy these books. Seriously. Good Strategy, Bad = Strategy and How to Decide will change how you think about running your com= pany.

  1. Document your biases. Write down what you believe about your market, your customer= s, your competition. Transform those beliefs into testable bets.

    =

  1. Run the strategy framework. Spend serious time on situation and diagnosis. Don't rush to solut= ions.

  1. Trust your gut, but verify it. Your instincts got you here. Don't let them be = drowned out by committee thinking.

You started this company because you saw someth= ing others didn't. That vision, that conviction, that willingness to ma= ke big bets - those are features, not bugs.

The market needs founders who trust themselves enough = to make bold moves. Your customers need you to have conviction about where = you're taking them.

So trust your gut. But make it strategic.

You've got this.

What's your experience with balancing gut instinc= t and strategic thinking? Hit reply and let me know - I read every response= .

Collin=C2=A0

PS - I=E2=80=99d love your = feedback on what else I can create for you all as a reward for pre-ordering= the book. Here are a few ideas: exclusive pre-order book club, video cours= e to accompany the workbook, a physical copy of the workbook (madlibs style= ), and access to a GPT with the full content of the book. Hit reply and let= me know.

PPS - if you= love audiobooks and can commit to a quick turnaround, I=E2=80=99m looking = for a few people to listen and help me find any issues. Hit reply if you=E2= =80=99re interested.=C2=A0

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