Return-Path: Delivered-To: andrew@sterlingcal.com Received: from reseller401.webserversystems.com by reseller401.webserversystems.com with LMTP id kKquKpUmy2dQKQYAchKAPA (envelope-from ) for ; Fri, 07 Mar 2025 11:02:13 -0600 Return-path: Envelope-to: andrew@sterlingcal.com Delivery-date: Fri, 07 Mar 2025 11:02:13 -0600 Received: from o172.ptr2130.mail.beehiiv.com ([159.183.140.149]:45820) by reseller401.webserversystems.com with esmtps (TLS1.2) tls TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256 (Exim 4.98.1) (envelope-from ) id 1tqb5Q-00000001o56-44qv for andrew@sterlingcal.com; Fri, 07 Mar 2025 11:02:13 -0600 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=P8eMWbFlsMwqt9zZ4vt6KZyqPv1FqmJOEm8bjTrABjA=; b=h85EPdxsm64wzn1zrzRmrzWxwQC1u3CHKk6fFz1RRoFEg2n1gghOYU2Vn4mQJsoGN0h3 ydw7tT/o64JInZ2xpfxUe5dRG+MOCpFYmKiG9GWfVuQ/N8IBPQvgUg+t0RFFN1Kg955CbK b9CTmfTBAfw3C+f7KfEc6ue4k0r0X88XblQ2H0rBZYgq/nge3AXf7/jTFLCrjVr5/bzvpF lmarBOYPXIeDQVqyFypDF1yK+CkXQIMwUJdW6Syn/UIFhgjRccP//yExM2lhOGY6mb6ksk Ropso9+78SIelxTu8Nu3kL8Wr+2NyPXPNX27LZ7pw6r2Z97CDP2dhgYcIDy7sZQQ== Received: by recvd-canary-847dc7f567-4qbgw with SMTP id recvd-canary-847dc7f567-4qbgw-1-67CB267B-DA 2025-03-07 17:01:47.583122363 +0000 UTC m=+2664405.972041407 Received: from NDAyMzQxODk (unknown) by geopod-ismtpd-5 (SG) with HTTP id h2X2Cd3hTIeU2afmdRzK3g Fri, 07 Mar 2025 17:01:47.508 +0000 (UTC) Content-Type: multipart/alternative; boundary=5ee1784feb365f1fa7985ebd30688e44a2e687f81467661d7a2175202398 Date: Fri, 07 Mar 2025 17:02:01 +0000 (UTC) From: Collin Stewart Mime-Version: 1.0 Message-ID: Subject: dream crushers Reply-To: Collin Stewart Feedback-ID: =?us-ascii?Q?3a88989e-a590-484f-8d98-3aece6670269=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+3a88989e-a590-484f-?= =?us-ascii?Q?8d98-3aece6670269=40unsub=2Ebeehiiv=2Ecom=3E=2C?= =?us-ascii?Q?_=3Chttps=3A=2F=2Fpredictablerevenue-newsletter=2Ebeehiiv=2Ecom=2Funsubscribe?= =?us-ascii?Q?=2FeyJ0eXAiOiJKV1QiLCJhbGciOiJIUzI1NiJ9=2Ee?= =?us-ascii?Q?yJzdWJzY3JpYmVyX2lkIjoiMWQxN2RjMjYtYzFk?= =?us-ascii?Q?Zi00NGUwLTgxMmEtODgzYjZhZDViNmJjIiwicG9?= =?us-ascii?Q?zdF9pZCI6IjNhODg5ODllLWE1OTAtNDg0Zi04ZD?= =?us-ascii?Q?k4LTNhZWNlNjY3MDI2OSIsImxhc3RfcmVzb3VyY?= =?us-ascii?Q?2VfZ3VpZCI6IlBvc3Q6M2E4ODk4OWUtYTU5MC00?= =?us-ascii?Q?ODRmLThkOTgtM2FlY2U2NjcwMjY5In0=2EUsZYddp?= =?us-ascii?Q?Tv7qxQaN8rnnkjx60CoDnhHIGFCRLTSPj4mA=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=2Fpredictablerevenue-newsletter=2Ebeehiiv?= =?us-ascii?Q?=2Ecom=2F=22=2C=22campaign=5Fid=22=3A=223a88989e-a590-484?= =?us-ascii?Q?f-8d98-3aece6670269=22=2C=22category=22=3A=22newsle?= =?us-ascii?Q?tter=22=2C=22email=5Fgenerated=5Fat=22=3A1741366907=2C=22?= =?us-ascii?Q?user=5Fid=22=3A=223c5b97ff-00a9-4acc-916d-c137b?= =?us-ascii?Q?ca24b1d=22}?= x-beehiiv-type: newsletter x-list-id: 3c5b97ff-00a9-4acc-916d-c137bca24b1d x-list-owner: x-newsletter: https://predictablerevenue-newsletter.beehiiv.com/p/dream-crushers x-newsletter-id: https://predictablerevenue-newsletter.beehiiv.com/ x-newsletter-signup: https://predictablerevenue-newsletter.beehiiv.com/subscribe X-SG-EID: =?us-ascii?Q?u001=2E7ozyt+tmjDsHnEocxX8pymFA2v5OOh2V4Pdr6hGVjZo99sLHT4OeEg7as?= =?us-ascii?Q?oEFtQzIa0qAOkk1QezFA4qrCcff9558yNK8x6zQ?= =?us-ascii?Q?0aLhxDCyAuB9kgcSLas3IIKR+fvCUJBBLhObljX?= =?us-ascii?Q?cjPuiZc4QNHuZ+S1OkJy2veAvSn3=2FrdNdWH=2Fiu2?= =?us-ascii?Q?e3LQmjPbdLduyyhhta3R5bLwfz5RTyPXpoBSjR8?= =?us-ascii?Q?Uo=2F6xtIOWDbWnQIxUqWyCrZpefIk0lbYKNHsPqH?= =?us-ascii?Q?g0rgHYFpLDzG4Aedzt1PdKBxi0s00bByqo8226r?= =?us-ascii?Q?rAZYpbxw=3D?= X-SG-ID: =?us-ascii?Q?u001=2ESdBcvi+Evd=2FbQef8eZF3BpTL9BgbK5wfSJMJGMsmprAVgeiC8iaV7rEmQ?= =?us-ascii?Q?+cYi2k7A0jo7vKiVAo7ctXrtTXYj7=2F8poesMqp=2F?= =?us-ascii?Q?HyY4E+oSECrQ6FOL9lWtBsbmzXaOri6c=2FcPyykz?= =?us-ascii?Q?TXOJZlwFTsIqUVbKbe8qPi8sCD3gq3tw8=2FD2yCU?= =?us-ascii?Q?FjjO5twFLiKu9znRDGqX8zhzXsmh4m86QX6vjp8?= =?us-ascii?Q?Po=2FnBzkD+XMphuCr=2FOtKy7W44DQOdS8cFCU3x+M?= =?us-ascii?Q?j3VaUzlq5FvA04KnsVZi2USfEw=3D=3D?= 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 --5ee1784feb365f1fa7985ebd30688e44a2e687f81467661d7a2175202398 Content-Transfer-Encoding: quoted-printable Content-Type: text/plain; charset=utf-8 Mime-Version: 1.0 Hello Andrew,=20 **_Book update_**_: Thank you to all the early ARC reviewers for sharing yo= ur reviews and comments! If you haven=E2=80=99t shared yours, your review i= s still helpful because I=E2=80=99ll be adding them to the website later th= is month. I=E2=80=99ve now submitted my first round of copy edit feedback a= nd we=E2=80=99re working on the design/typesetting of the book (check the b= ottom for a sneak preview). _ _**Community update**__: our next Revenue Roundtable is March 14th (next Fr= iday) at 930am PT, we have a few more spots and then I=E2=80=99ll be instit= uting a waitlist. Hit me back if you=E2=80=99re interested in joining us._ _Here=E2=80=99s an early review from Susan Abbott, founder of Just Know: _ _=E2=80=9C_I=E2=80=99m absolutely loving the book. I initially thought it w= ould be a light read, reinforcing things I already knew or had read elsewhe= re=E2=80=94but it has completely blown me away. So many aha moments have ma= de me pause and reflect on what they mean for my startup.=E2=80=9D=20 _**tl;dr**__ _ * _Play Dream Crushers as a fun way of testing / validating new startup ide= as _ * _Founder Story: How Courtney Krstich (EarthaPro) found her first customer= s over Instagram and at conferences (_[_check it out on Spotify_](https://o= pen.spotify.com/episode/6BkRb4BOy8goT9LPrtu6LQ)_)_ I recently connected with a fellow founder who stumbled upon what seemed li= ke a massive gap in the market. Their enthusiasm was contagious, and our co= nversation inspired today's post.=20 Here=E2=80=99s a bit about their situation: They were convinced they had a surefire opportunity=E2=80=94a huge, untappe= d market with only around 10% penetration, based on their calculations. The= y had the technical skills to build the software, but there was a catch: th= e product required hardware manufacturing. That meant real capital, establi= shed supply chain partners, and a supporting team. At just 19 years old, they had zero capital, no significant manufacturing n= etwork, and couldn=E2=80=99t find a co-founder to help shoulder the load. T= hey felt stuck=E2=80=94as if all the puzzle pieces for a successful busines= s existed, but they couldn=E2=80=99t get the first domino to fall. _Does this resonate? Let me know if you started out with similar ideas and = how you broke through. _ Their situation brought me back to the early days of my first company, volt= ageCRM, when I faced exactly this kind of dilemma. Here=E2=80=99s an exerci= se we used that helped me (and might help you) break through: **Dream Crushers** I don=E2=80=99t remember who created the game, but I vividly recall Mack Fl= avelle MC=E2=80=99ing our event and turning the act of getting your dreams = crushed into a cathartic and hilarious experience. We played it over beers = at our co-working space, among familiar faces. It was a safe space=E2=80=A6= kinda. Here=E2=80=99s how Dream Crushers works: * The Founder=E2=80=99s goal is to convince The Crowd their dream is still = alive. * The Panel=E2=80=99s goal is to convince The Crowd that the Founder=E2=80= =99s dream is dead. The Panel assumes the role of disgruntled, skeptical VC= s whose sole mission is to find fatal flaws in the Founder=E2=80=99s pitch. * The Crowd=E2=80=99s role is simple: decide who wins by cheering loudly fo= r whichever side made the most compelling arguments. The Structure: 1. Pitch: The Founder gets 2 minutes to present their idea. 2. Preparation: The Panel has 2 minutes to quickly research and prepare the= ir toughest questions. 3. Hell breaks loose: 5 minutes of intense Q&A and spirited debate between = Founder and Panel. 4. Judgement: The Crowd cheers for the winner based on the strength of the = arguments. Yes, it's intimidating=E2=80=94but somehow, knowing the Panel was instructe= d to act like assholes actually made it easier to digest criticism. We later adapted Dream Crushers into a fun version for pitch practice or un= winding after a tough week. Here=E2=80=99s how we tweaked it: Instead of pitching real startup ideas, founders drew randomly from three h= ats: * Hat 1: Startup name * Hat 2: Market vertical (sales, healthcare, fintech, etc.) * Hat 3: Product type (SaaS, marketplace, consumer app, hardware, etc.) Participants had 1 minute think, 1 minute to share the value proposition an= d market hypothesis and 2 minutes to defend their new idea.. We ran it as a ladder-style tournament, pitting two founders head-to-head, = with The Crowd deciding who moved forward. It was a fun way to practice thi= nking on our feet and have a few laughs with our fellow co-working space in= habitants.=20 Back to my conversation with the new founder, my advice was for them to pla= y Dream Crusher Solitaire. They should give themselves an hour to draft a d= ocument clearly laying out their hypothesis. Then, they should take on the = role of the panel and give themselves another hour to ruthlessly tear apart= their own hypothesis. Afterward, they can decide for themselves or toss th= e documents into an LLM and let Skynet decide. What=E2=80=99s the toughest feedback you=E2=80=99ve ever gotten on your sta= rtup? Hit reply and let me know.=C2=A0 Collin=C2=A0 PS - I=E2=80=99ve been interviewing founders lately to learn about their pr= oduct-market fit journey and I=E2=80=99d like your feedback. Have a look at= the below preview. Do these belong in a separate post? Or are you good wit= h a summary appended after my regular post?=C2=A0 ### **Founder Spotlight: Courtney Krstich, EarthaPro** I sat down with Courtney, to talk about her journey to product-market fit. = Courtney=E2=80=99s story is a masterclass in customer discovery, validation= , and persistence. She started her career in field sales, working directly with landscapers an= d lawn care businesses. Over time, she noticed a glaring problem: these bus= inesses were running on pen, paper, Apple Notes, and Excel, with no streaml= ined system to track jobs, invoicing, or operations. When she asked why the= y weren=E2=80=99t using software, the response was always the same=E2=80=94= it was too expensive, too complicated, or just not built for them. That was the spark. Courtney teamed up with an old friend, and software dev= eloper, and started Eartha Pro=E2=80=94named after her cat. But before quit= ting her job, she put in the work. She did 50+ customer interviews, attende= d industry trade shows, and joined a pre-accelerator to validate the idea. Her first customers didn=E2=80=99t come from ads or outbound emails. They c= ame from Instagram. Want to hear the full story? Check out [the episode her= e](https://open.spotify.com/episode/6BkRb4BOy8goT9LPrtu6LQ).=C2=A0 **Interior Sample Design Preview ** Let me know what you think of the font.=20 View image: (https://media.beehiiv.com/cdn-cgi/image/fit=3Dscale-down,forma= t=3Dauto,onerror=3Dredirect,quality=3D80/uploads/asset/file/cc49af04-7db9-4= 868-990c-37a17bc826b8/CleanShot_2025-03-07_at_07.03.07.png?t=3D1741359820) 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://predictablerevenue-newsletter.beehiiv.com/p/dream-crushers --5ee1784feb365f1fa7985ebd30688e44a2e687f81467661d7a2175202398 Content-Transfer-Encoding: quoted-printable Content-Type: text/html; charset=utf-8 Mime-Version: 1.0 dream crushers
<= td align=3D"center" valign=3D"top" style=3D"border:0px solid #FFFFFF;border= -radius:10px;background-color:#FFFFFF;" class=3D"c">

March 07, 2025   |   Read Online

<= table role=3D"none" width=3D"100%" border=3D"0" cellspacing=3D"0" cellpaddi= ng=3D"0" align=3D"center">

dream crushers

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

Book update: Thank you to all the early ARC reviewers for sharing your= reviews and comments! If you haven=E2=80=99t shared yours, your review is = still helpful because I=E2=80=99ll be adding them to the website later this= month. I=E2=80=99ve now submitted my first round of copy edit feedback and= we=E2=80=99re working on the design/typesetting of the book (check the bot= tom for a sneak preview).

They were convinced they had a surefire opportunity=E2=80=94= a huge, untapped market with only around 10% penetration, based on their ca= lculations. They had the technical skills to build the software, but there = was a catch: the product required hardware manufacturing. That meant real c= apital, established supply chain partners, and a supporting team.

=

Participants had 1 minute think, 1 minute to share the value= proposition and market hypothesis and 2 minutes to defend their new idea..=

= = <= tr>

Hello Andrew,

Community update<= i>: our next Revenue Roundtable is March 14th (next Friday) at 930am PT, we= have a few more spots and then I=E2=80=99ll be instituting a waitlist. Hit= me back if you=E2=80=99re interested in joining us.

Here=E2=80=99s an early review from Susan Abbott= , founder of Just Know:
=E2=80=9CI=E2=80=99= m absolutely loving the book. I initially thought it would be a light read,= reinforcing things I already knew or had read elsewhere=E2=80=94but it has= completely blown me away. So many aha moments have made me pause and refle= ct on what they mean for my startup.=E2=80=9D

tl;dr=C2=A0

  • Play Dream Crushers = as a fun way of testing / validating new startup ideas

    • =

  • = Founder Story: How Courtney Krstich (EarthaPro) found her first customer= s over Instagram and at conferences (che= ck it out on Spotify)

I = recently connected with a fellow founder who stumbled upon what seemed like= a massive gap in the market. Their enthusiasm was contagious, and our conv= ersation inspired today's post.

Here=E2=80=99s a bit about their situation:

At just 19 years old, they had zero capita= l, no significant manufacturing network, and couldn=E2=80=99t find a co-fou= nder to help shoulder the load. They felt stuck=E2=80=94as if all the puzzl= e pieces for a successful business existed, but they couldn=E2=80=99t get t= he first domino to fall.

Does = this resonate? Let me know if you started out with similar ideas and how yo= u broke through.

Their situa= tion brought me back to the early days of my first company, voltageCRM, whe= n I faced exactly this kind of dilemma. Here=E2=80=99s an exercise we used = that helped me (and might help you) break through:

Dream Crushers

I don=E2=80=99t remember who created the game, but I vividly recal= l Mack Flavelle MC=E2=80=99ing our event and turning the act of getting you= r dreams crushed into a cathartic and hilarious experience. We played it ov= er beers at our co-working space, among familiar faces. It was a safe space= =E2=80=A6 kinda.

Here=E2=80=99s h= ow Dream Crushers works:

  • The Founder=E2= =80=99s goal is to convince The Crowd their dream is still alive.

  • The Panel=E2=80=99s goal is to convince The Crowd that the Founder=E2= =80=99s dream is dead. The Panel assumes the role of disgruntled, skeptical= VCs whose sole mission is to find fatal flaws in the Founder=E2=80=99s pit= ch.

  • The Crowd=E2=80=99s role is simple: decide who wins by c= heering loudly for whichever side made the most compelling arguments.

T= he Structure:

  1. Pitch: The F= ounder gets 2 minutes to present their idea.

  2. Preparation: Th= e Panel has 2 minutes to quickly research and prepare their toughest questi= ons.

  3. Hell breaks loose: 5 minutes of intense Q&A and spirite= d debate between Founder and Panel.

  4. Judgement: The Crowd che= ers for the winner based on the strength of the arguments.

    5. <= /ol>

Yes, it's intimidating=E2=80= =94but somehow, knowing the Panel was instructed to act like assholes actua= lly made it easier to digest criticism.

We later adapted Dream Crushers into a fun version for pitch pract= ice or unwinding after a tough week. Here=E2=80=99s how we tweaked it:

<= span style=3D"color:rgb(44, 62, 80);">Instead of pitching real startup idea= s, founders drew randomly from three hats:

    Hat 2: Market vertical (sales, healthc= are, fintech, etc.)

  • Hat 3: Product type (SaaS, marketplace= , consumer app, hardware, etc.)

We ran it as a ladder-style tour= nament, pitting two founders head-to-head, with The Crowd deciding who move= d forward. It was a fun way to practice thinking on our feet and have a few= laughs with our fellow co-working space inhabitants.

Back to my conversation with the new founder, my advi= ce was for them to play Dream Crusher Solitaire. They should give themselve= s an hour to draft a document clearly laying out their hypothesis. Then, th= ey should take on the role of the panel and give themselves another hour to= ruthlessly tear apart their own hypothesis. Afterward, they can decide for= themselves or toss the documents into an LLM and let Skynet decide.=

What=E2=80=99s the toughest feedback yo= u=E2=80=99ve ever gotten on your startup? Hit reply and let me know.=C2=A0<= /span>

Collin=C2=A0

PS - I=E2=80=99ve been interviewing founders lately t= o learn about their product-market fit journey and I=E2=80=99d like your fe= edback. Have a look at the below preview. Do these belong in a separate pos= t? Or are you good with a summary appended after my regular post?=C2=A0

Founder Spotlight: C= ourtney Krstich, EarthaPro

I= sat down with Courtney, to talk about her journey to product-market fit. C= ourtney=E2=80=99s story is a masterclass in customer discovery, validation,= and persistence.

She started h= er career in field sales, working directly with landscapers and lawn care b= usinesses. Over time, she noticed a glaring problem: these businesses were = running on pen, paper, Apple Notes, and Excel, with no streamlined system t= o track jobs, invoicing, or operations. When she asked why they weren=E2=80= =99t using software, the response was always the same=E2=80=94it was too ex= pensive, too complicated, or just not built for them.

That was the spark. Courtney teamed up with an old fri= end, and software developer, and started Eartha Pro=E2=80=94named after her= cat. But before quitting her job, she put in the work. She did 50+ custome= r interviews, attended industry trade shows, and joined a pre-accelerator t= o validate the idea.

Her first cu= stomers didn=E2=80=99t come from ads or outbound emails. They came from Ins= tagram. Want to hear the full story? Check out the episode here.=C2=A0

Interior Sample Design Pre= view

Let me know what you th= ink of the font.

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