Return-Path: Delivered-To: andrew@sterlingcal.com Received: from reseller401.webserversystems.com by reseller401.webserversystems.com with LMTP id EM44NLCMzWjNbwQAchKAPA (envelope-from ) for ; Fri, 19 Sep 2025 12:02:40 -0500 Return-path: Envelope-to: andrew@sterlingcal.com Delivery-date: Fri, 19 Sep 2025 12:02:40 -0500 Received: from o171.ptr9046.mail.beehiiv.com ([159.183.140.157]:40406) by reseller401.webserversystems.com with esmtps (TLS1.2) tls TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256 (Exim 4.98.1) (envelope-from ) id 1uzeVM-00000001H1C-0Yrf for andrew@sterlingcal.com; Fri, 19 Sep 2025 12:02:40 -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=X4X1IKdbu7pS6+7Qpk5+xjbk1P5XAgdCjMOGqUSJgSM=; b=HY+SLA9knqFLc2EY+EaoDhwrduEcipFpg5kkAbHVe3MdgOc0CNbOynzQknC+O9Ir9e9J 5/haOSu1fCk7b/jwssqOGZ0b/KxhI8IXisj6C43ELyu6KU8ErCUoXCAKC4kWVTW8SKuhmA iM1gYe2gTa+tZOQ776RU27UKY1K9jyHI83Z0nLY82UG05V77gEihT7uap7Q8r1bSjVbuJ+ o+7bwsOBZqqvaav6edscu3o1HhCdbXJ/ztxpx+G1ZxRn2cd3iLXqqooJ5KeZCe9fZ9pllX uW6RdyV3ZjcPCkIxQ5wR3+uboeS8BRNlo7OKnrpQEHzIYAxOobUXPC3WXu6UY9yA== Received: by recvd-67f5964c58-sc2gw with SMTP id recvd-67f5964c58-sc2gw-1-68CD8C7B-135 2025-09-19 17:01:47.678290717 +0000 UTC m=+9245848.586903906 Received: from NDAyMzQxODk (unknown) by geopod-ismtpd-35 (SG) with HTTP id qNxzfHYHRiyGI0KHcLSqow Fri, 19 Sep 2025 17:01:47.633 +0000 (UTC) Content-Type: multipart/alternative; boundary=99536b162088a19acfcdcfe5886df26d80179bea5989f69713a02fefa92c Date: Fri, 19 Sep 2025 17:02:29 +0000 (UTC) From: Collin Stewart Mime-Version: 1.0 Message-ID: Subject: We All Feel Like Impostors Reply-To: Collin Stewart Feedback-ID: =?us-ascii?Q?a9b62d7e-a9c5-4c75-aa25-a9546a5b66dd=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+a9b62d7e-a9c5-4c75-?= =?us-ascii?Q?aa25-a9546a5b66dd=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?hZDViNmJjIiwicG9zdF9pZCI6ImE5YjYyZDdlLW?= =?us-ascii?Q?E5YzUtNGM3NS1hYTI1LWE5NTQ2YTViNjZkZCIsI?= =?us-ascii?Q?mxhc3RfcmVzb3VyY2VfZ3VpZCI6IlBvc3Q6YTli?= =?us-ascii?Q?NjJkN2UtYTljNS00Yzc1LWFhMjUtYTk1NDZhNWI?= =?us-ascii?Q?2NmRkIn0=2ETayF1xx4tm8VS5LAsWdPYjGiJT1ZGi?= =?us-ascii?Q?0HdLtllYAVrU4=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=22a?= =?us-ascii?Q?9b62d7e-a9c5-4c75-aa25-a9546a5b66dd=22=2C=22c?= =?us-ascii?Q?ategory=22=3A=22newsletter=22=2C=22email=5Fgenerated=5F?= =?us-ascii?Q?at=22=3A1758301307=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/we-all-feel-like-impostors 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+fvCUJBB2Lqi6Y=2F?= =?us-ascii?Q?UaE+tER0rh3E31XJ0Bl7Tef+dVsAUj4nwCg6iCx?= =?us-ascii?Q?4Mx7Vo=2F4=2F3hR9qoKcTZ6Xauw0IgIQLvTwd6jUKe?= =?us-ascii?Q?XCpu3B81=2FiJXkRSl2Yz=2FICCeSybRuom76zP7egZ?= =?us-ascii?Q?xYLuwarASE7Na24UAGVY+fQRH26foaTPbN7Ntuo?= =?us-ascii?Q?=2FSc4bL9I=3D?= X-SG-ID: =?us-ascii?Q?u001=2ESdBcvi+Evd=2FbQef8eZF3BpTL9BgbK5wfSJMJGMsmprD1ZcmFObA4po1bG?= =?us-ascii?Q?aUE6gycJ+LfRoc8X0Wm0MSorFVcoWHrIixZYD9z?= =?us-ascii?Q?w25Z143eglkAJWbQrLxndYtch6lhNuMZAjzTdhS?= =?us-ascii?Q?+p7WkO424Ipk13O34SdX8bx0Vq1+NisSaeD1d9x?= =?us-ascii?Q?dBSWF94wwUnCrcy+1KkC65VMSs12OOvBeJx6V56?= =?us-ascii?Q?bMoybmz0hF=2FzRFsA0zzjLPbfMn8Ie1zwczVBtxe?= =?us-ascii?Q?NfTihzMce3Sw+QeOx5wL1KUvPtyGF2rPp7bNWTC?= =?us-ascii?Q?lyzU2SrEkOd3onLebufkAVdmXGgTO4K4ACJKmwT?= =?us-ascii?Q?Nh1CEwBjmCjvk=2FNJaJBYmktmp=2FLfq4qccYe5cgz?= =?us-ascii?Q?1RbhwV=2FSwEs3kqL?= To: "andrew@sterlingcal.com" X-Entity-ID: u001.RuZ2+X9IBGtjUb8qq3teHQ== X-Spam-Status: No, score=0.4 X-Spam-Score: 4 X-Spam-Bar: / X-Spam-Flag: NO --99536b162088a19acfcdcfe5886df26d80179bea5989f69713a02fefa92c Content-Transfer-Encoding: quoted-printable Content-Type: text/plain; charset=utf-8 Mime-Version: 1.0 Hello Andrew,=20 _**Pre-order update**__: I created the LinkedIn mini-course I mentioned a f= ew weeks ago and have added it to the pre-sale benefits doc. If that sounds= great, you can _[_pre-order here_](https://www.amazon.com/Terrifying-Art-F= inding-Customers-Sleep-Deprived/dp/1774586134)_, send me a screenshot, and = I=E2=80=99ll add you to the doc. _ _**Next up pre-order benefit**__: I=E2=80=99m going to leave this one up to= you all, here are two ideas I had that might be useful, vote by sending me= a screenshot of your pre-order receipt. _ 1. _I=E2=80=99ll build you a list of 25 podcasts you=E2=80=99d be a fit to = go on_ 2. _I=E2=80=99ll create a baby board book version of The Terrifying Art of = Finding Customers and donate the profit to Children=E2=80=99s Hospital (see= PS for example) _ _Now onto the newsletter._ I almost didn't write this book. We've got over 180 presales already, which blows me away =E2=80=94 and it a= lmost never happened. Not because I couldn't afford the $37K to publish it,= or because I was too busy, or because I didn't know the process. The real blocker was confidence. ## The Voice in Our Heads For months, I sat with this nagging voice: _"Do I even have the right to wr= ite this book?"_ I'd built Predictable Revenue for 13 years. Had 10 engineers at one point. = Generated millions in revenue. But when it came time to share what I'd lear= ned, that voice got loud: _"Is my experience even valid, or am I just milki= ng one story?"_ Sound familiar? I had a call with my friend Kenny last week. He's been sitting on a book id= ea for years =E2=80=94 has all this theory around product-market fit that I= 've seen work in practice. But he won't write it yet. "I feel like I got a lot of theory," he told me. "It's only been in the las= t month where I feel like, okay yeah, it's working. I'm applying the theory= , and it's working." He's founded multiple startups, helped dozens of founders, and regularly po= sts essays on Hacker News that founders thank him for months later. But he'= s waiting until he feels "qualified enough." ## The Universal Question I found myself asking Kenny: _"Is my experience even valid?"_ And then I realized it connected to something bigger. I=E2=80=99ve bootstra= pped all of my startups using services to get them off the ground or the re= venue from our services business to fund their development. This puts me on= e foot in the agency founder space and one foot in the tech startup founder= space.=C2=A0 I feel like every founder in my situation is asking themselves the same que= stion: "Am I a real startup founder? Or am I just a guy who wasted millions= of dollars of services profit on developers?"=C2=A0 I=E2=80=99ve started multiple software companies, at peak [Carb.io](https:/= /Carb.io) had 10 engineers and $1m in ARR. And I=E2=80=99m still asking mys= elf, =E2=80=9Cam I really a software startup founder?=E2=80=9D That's the question, isn't it? The one we all ask but rarely say out loud. _Am I really qualified for this?_ _Do I actually know what I'm doing?_ _Wha= t if everyone finds out I'm just figuring it out as I go?_ I see this everywhere. The founder with 30 customers wondering if they're "= real" yet. The CEO who just raised Series A asking if they deserve to be in= the room. The consultant with years of experience second-guessing whether = their advice is worth anything. We're all walking around carrying this secret fear that we're frauds about = to be exposed. ## The You-Shaped Curve (it=E2=80=99s a pun, you=E2=80=99ll get it later) Here's what's wild: the more qualified you actually are, the more impostor = syndrome hits you. Kenny talked about this during our call. He's spent years studying what mak= es companies succeed or fail. He=E2=80=99s a true mad scientist of product-= market fit =E2=86=92 he called the fact that AI would eat our SDR agency in= ~2019, well before the ChatGPT moment made it truly obvious. But he won't write about it yet because he wants more "proof." Meanwhile, there are people pumping out courses and books with a fraction o= f his experience, making bank off theories they've never tested. They don't= suffer from impostor syndrome because they don't know enough to question t= hemselves. The Dunning-Kruger effect: the more you know, the more you realize you don'= t know, and the less confident you feel. Kenny put it perfectly: _"We learn way more from failure. People who succee= d too quick and too fast get arrogant, and that can blow up in a bad way. W= hereas people who struggle and fail for a long time... I suspect I'm actual= ly more competent than it feels like I am."_ The cruel irony is that impostor feelings often show up precisely when you'= re most qualified to help. You feel like a fraud because you remember all your mistakes. You know how = much you struggled. You can see the gap between where you are and where you= want to be. But that struggling? Those mistakes? That gap? They're exactly what makes y= our perspective valuable. Kenny talked about feeling like he was in "the valley of despair" for years= =E2=80=94 that phase where your confidence crashes as you realize how much= you don't know. But now he's coming out the other side: _"I feel like I'm = starting to hit that other side of the Dunning-Kruger, where my confidence = is catching up with my competence."_ The people who need your help are still in that valley. They need someone w= ho remembers what it was like to be there. ## What Success Actually Looks Like I used to think successful people were the ones who never doubted themselve= s. Turns out, the opposite is true. Kenny shared something that stuck with me. He said even now, with his curre= nt company taking off, he feels terrified about the next phase: _"I feel li= ke I've got the first part figured out. But then there's this problem of bu= ilding a machine that scales. And I haven't done that yet. So I feel like I= 'm gonna be stumbling through the dark, bumping my face, stubbing my toe ag= ain."_ This from a guy who's about to speak at a conference where the entire audie= nce is his ideal customer profile. Who has 30+ customers already using his = product. Who's getting the kind of gushing feedback every founder dreams of= . Success doesn't eliminate impostor feelings. It just changes what you feel = like an impostor about. ## The Only Way Is Through I wrote the book anyway. Despite the voice telling me I wasn't qualified. D= espite wondering if my experience with one company was enough to help other= founders. Not because I conquered my impostor feelings, but because I decided to act = despite them. The response has been better than I imagined. Not just the presales =E2=80= =94 but the notes from you all saying it's exactly what you needed to hear = or saying you=E2=80=99ve forwarded it to a family member so they can better= understand what you=E2=80=99re going through.=C2=A0 The only way through impostor feelings is to act anyway. Share your story. = Test your ideas. Put yourself out there. Your experience matters. Your struggles taught you something. Someone needs= to hear what you learned. The results =E2=80=94 over 180 presales for a book that almost never existe= d =E2=80=94 validate what fear told you to hide. _What's something you've been holding back on because you don't feel "quali= fied" enough? Hit reply and tell me =E2=80=94 I'd love to hear._ Collin=C2=A0 **PS -** If you want to grab one of those 180+ presales, you can [order the= book here](https://www.amazon.com/Terrifying-Art-Finding-Customers-Sleep-D= eprived/dp/1774586134). It officially launches next month and I have some e= xtras for folks who pre-order.=20 **PPS - **here=E2=80=99s roughly what I=E2=80=99m thinking for the baby boa= rd book:=20 View image: (https://media.beehiiv.com/cdn-cgi/image/fit=3Dscale-down,forma= t=3Dauto,onerror=3Dredirect,quality=3D80/uploads/asset/file/3e818ae4-9031-4= d32-b6d5-c7a515c7c9f9/Gemini_Generated_Image_xd6jyixd6jyixd6j.png?t=3D17582= 95957) Caption:=20 =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/we-all-feel-like-impostors --99536b162088a19acfcdcfe5886df26d80179bea5989f69713a02fefa92c Content-Transfer-Encoding: quoted-printable Content-Type: text/html; charset=utf-8 Mime-Version: 1.0 We All Feel Like Impostors
<= 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">
=

The You-Shaped Curve (= it=E2=80=99s a pun, you=E2=80=99ll get it later)

<= td class=3D"dd" align=3D"left" style=3D"padding:0px 15px;text-align:left;wo= rd-break:break-word;">

Here's what's wild: the more qualified = you actually are, the more impostor syndrome hits you.

= =

Septemb= er 19, 2025   |   Read Online

We All Feel Like Impostors

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

Hello Andrew,

Pre-order update= : I created the Linked= In mini-course I mentioned a few weeks ago and have added it to the pre-sal= e benefits doc. If that sounds great, you can pre-order here, send me a screenshot, and I=E2=80=99ll add= you to the doc.

<= i>Next up pre-order benefit: I=E2=80=99m going to leave this one up to you all, here are t= wo ideas I had that might be useful, vote by sending me a screenshot of you= r pre-order receipt.

    =

  1. I=E2=80=99ll build you a list of 25 podcasts you=E2=80=99d be = a fit to go on

  2. I=E2=80=99ll create a baby b= oard book version of The Terrifying Art of Finding Customers and donate the= profit to Children=E2=80=99s Hospital (see PS for example)

    =

Now onto the n= ewsletter.

I almost= didn't write this book.

We've got over 180 presales already, which blows me away =E2=80= =94 and it almost never happened. Not because I couldn't afford the $37= K to publish it, or because I was too busy, or because I didn't know th= e process.

The real blo= cker was confidence.

The Voice in Our Heads

For months, I sat with this nagging voice: "Do I even have the right to write this= book?"

I'= d built Predictable Revenue for 13 years. Had 10 engineers at one point. Ge= nerated millions in revenue. But when it came time to share what I'd le= arned, that voice got loud: <= i>"Is my experience even valid, or am I just milking one story?"<= /i>

Sound familiar?

I had a call with my frien= d Kenny last week. He's been sitting on a book idea for years =E2=80=94= has all this theory around product-market fit that I've seen work in p= ractice. But he won't write it yet.

"I feel like I got a lot of theory," he told m= e. "It's only been in the last month where I feel like, okay yeah,= it's working. I'm applying the theory, and it's working."=

He's founded multi= ple startups, helped dozens of founders, and regularly posts essays on Hack= er News that founders thank him for months later. But he's waiting unti= l he feels "qualified enough."

The Universal Question

I found myself asking Kenny: "Is my experience even valid?&quo= t;

And then I reali= zed it connected to something bigger. I=E2=80=99ve bootstrapped all of my s= tartups using services to get them off the ground or the revenue from our s= ervices business to fund their development. This puts me one foot in the ag= ency founder space and one foot in the tech startup founder space.=C2=A0

I feel like every founder= in my situation is asking themselves the same question: "Am I a real = startup founder? Or am I just a guy who wasted millions of dollars of servi= ces profit on developers?"=C2=A0

I=E2=80=99ve started multiple software companies, at peak Carb.io had 10 engineers and $1m in ARR. And I=E2=80= =99m still asking myself, =E2=80=9Cam I really a software startup founder?= =E2=80=9D

That's th= e question, isn't it? The one we all ask but rarely say out loud.

Am I really qualified for= this?=C2=A0Do I actually know what I'm doing?<= /i>=C2=A0What if everyone finds out I'm just figu= ring it out as I go?

We're all walking around carrying this secret = fear that we're frauds about to be exposed.

Kenny talked about this during our call. He= 's spent years studying what makes companies succeed or fail. He=E2=80= =99s a true mad scientist of product-market fit =E2=86=92 he called the fac= t that AI would eat our SDR agency in ~2019, well before the ChatGPT moment= made it truly obvious.

But he won't write about it yet because he wants more "proof.&quo= t;

Meanwhile, there are= people pumping out courses and books with a fraction of his experience, ma= king bank off theories they've never tested. They don't suffer from= impostor syndrome because they don't know enough to question themselve= s.

The Dunning-Kruger e= ffect: the more you know, the more you realize you don't know, and the = less confident you feel.

= "We learn way more from failure. People who succeed too quick and too = fast get arrogant, and that can blow up in a bad way. Whereas people who st= ruggle and fail for a long time... I suspect I'm actually more competen= t than it feels like I am."

The cruel irony is that impostor feelings often show up preci= sely when you're most qualified to help.

You feel like a fraud because you remember all your m= istakes. You know how much you struggled. You can see the gap between where= you are and where you want to be.

But that struggling? Those mistakes? That gap? They're exac= tly what makes your perspective valuable.

Kenny talked about feeling like he was in "the vall= ey of despair" for years =E2=80=94 that phase where your confidence cr= ashes as you realize how much you don't know. But now he's coming o= ut the other side: "I= feel like I'm starting to hit that other side of the Dunning-Kruger, w= here my confidence is catching up with my competence."

<= /td>

The people who need your help are = still in that valley. They need someone who remembers what it was like to b= e there.

What Success Actually Looks Like

I used to think successful people were the ones who n= ever doubted themselves. Turns out, the opposite is true.

Kenny shared something that stuck with m= e. He said even now, with his current company taking off, he feels terrifie= d about the next phase: &q= uot;I feel like I've got the first part figured out. But then there'= ;s this problem of building a machine that scales. And I haven't done t= hat yet. So I feel like I'm gonna be stumbling through the dark, bumpin= g my face, stubbing my toe again."

This from a guy who's about to speak at a conferen= ce where the entire audience is his ideal customer profile. Who has 30+ cus= tomers already using his product. Who's getting the kind of gushing fee= dback every founder dreams of.

Success doesn't eliminate impostor feelings. It just changes wh= at you feel like an impostor about.

The Only Way Is Through

I wrote the book anyway. Despite the voice = telling me I wasn't qualified. Despite wondering if my experience with = one company was enough to help other founders.

Not because I conquered my impostor feelings, but b= ecause I decided to act despite them.

The response has been better than I imagined. Not just the p= resales =E2=80=94 but the notes from you all saying it's exactly what y= ou needed to hear or saying you=E2=80=99ve forwarded it to a family member = so they can better understand what you=E2=80=99re going through.=C2=A0

The only way through impost= or feelings is to act anyway. Share your story. Test your ideas. Put yourse= lf out there.

Your expe= rience matters. Your struggles taught you something. Someone needs to hear = what you learned.

The= results =E2=80=94 over 180 presales for a book that almost never existed = =E2=80=94 validate what fear told you to hide.

What's something you've been holding bac= k on because you don't feel "qualified" enough? Hit reply and= tell me =E2=80=94 I'd love to hear.

Collin=C2=A0

PS - If you want to grab one of those 180+ presales, you can <= a class=3D"link" href=3D"https://link.mail.beehiiv.com/ss/c/u001.UY7-jEMcRL= Z5W6M0bzLpmzKZu4CMZ-4VPqYNLlg6yrGxR2XQhddm9dZyX6mpnTOell2BYjET-Y8l9HDSfj1AJ= Qh-u__Ozm5nzjGP54xQkGt8BkBwNf31D79F3CPl6rqE0csmgiDjAQi8JfWYU1YHq8qLIL3rukeI= oNRtPc66neihCiQ-9xchQDhpEmGm0Bdye4gdY1_CgKD-VDmpZ2T6BJCORbQzitB685s4L9rp79_= kQ_OEzCi9dVACkF4swd7sDahQ9XmC2zvlgQU7KfKJIjczMrwlrBT3vhkWfpp6V045KVes-55c9r= yDA2DLDPcU/4k1/TEf32wWJTxKj5zJkalDBeQ/h7/h001.WvgR2Bl05LYGU_oyV8AUFIvrOE-f5= g7714iO9amviNk" target=3D"_blank" rel=3D"noopener noreferrer nofollow">order the book here. It= officially launches next month and I have some extras for folks who pre-or= der.

PPS - here=E2=80=99s roughly what I=E2= =80=99m thinking for the baby board book:

<= /tr>
3D"yt"3D"in"
 
=

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