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boundary=7e182b9e568533dd2dc140f07069cdcdfd6da9e9c9710d0a1288748a0f79 Date: Fri, 17 Oct 2025 17:02:42 +0000 (UTC) From: Collin Stewart Mime-Version: 1.0 Message-ID: Subject: You Need to Do It Yourself First Reply-To: Collin Stewart Feedback-ID: =?us-ascii?Q?0f7a3fbe-741e-4489-994f-c3b02cee9008=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+0f7a3fbe-741e-4489-?= =?us-ascii?Q?994f-c3b02cee9008=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?hZDViNmJjIiwicG9zdF9pZCI6IjBmN2EzZmJlLT?= =?us-ascii?Q?c0MWUtNDQ4OS05OTRmLWMzYjAyY2VlOTAwOCIsI?= =?us-ascii?Q?mxhc3RfcmVzb3VyY2VfZ3VpZCI6IlBvc3Q6MGY3?= =?us-ascii?Q?YTNmYmUtNzQxZS00NDg5LTk5NGYtYzNiMDJjZWU?= =?us-ascii?Q?5MDA4In0=2EZXbXuWNsWFK51K3WsNvbekBTgm-do1?= =?us-ascii?Q?rudarFJ3e7bFw=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?f7a3fbe-741e-4489-994f-c3b02cee9008=22=2C=22c?= =?us-ascii?Q?ategory=22=3A=22newsletter=22=2C=22email=5Fgenerated=5F?= =?us-ascii?Q?at=22=3A1760720544=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/you-need-to-do-it-yourself-first 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+fvCUJBB+9XZVVa?= =?us-ascii?Q?8gM9SOPqsmHFW+eBSxW6COptE=2FgdElXFfIXgtqj?= =?us-ascii?Q?eAv2tyrLjg0eKDWA5pacIXiEEtZQZnOsq4OqKZD?= =?us-ascii?Q?EtliEhmn3niLE96LHmPrnFx2KeN0lsCgvWJPpSs?= =?us-ascii?Q?R+MaI4OPQVr2oY0m9zSZhqeBpKZd1QjRw0E8Wvt?= =?us-ascii?Q?eB=2FeG8jQ=3D?= X-SG-ID: =?us-ascii?Q?u001=2ESdBcvi+Evd=2FbQef8eZF3BpTL9BgbK5wfSJMJGMsmprD1ZcmFObA4po1bG?= =?us-ascii?Q?aUE6gycJ+LfRoc8X0Wm0MSorFVcoWHrIixZYD9z?= =?us-ascii?Q?w25Z143eglkAJWbQrLxndYtch6lhNuMZAjzTdhS?= =?us-ascii?Q?+p7WkO424Ipk13O34SdX8bx0Vq1+NisSaeD1NDu?= =?us-ascii?Q?lUEUfLAhdIsdPIRTQf2TsvOAsEYr02=2FM73O98KA?= =?us-ascii?Q?Rg3WO5bo4JSU5tgFzfjsAdzOEtpFkg1WlLjoA8X?= =?us-ascii?Q?EuhASQRCWKjH87ZqTKqk91demuA9rzvWhqhbE8l?= =?us-ascii?Q?sHB5BmcCWEJewl=2FPkaj1YiB90qqnSReUhp2w7HN?= =?us-ascii?Q?GufPkhVIlnyquLlI3NqfIsmKgLBzJH5avMF79sz?= =?us-ascii?Q?7v4iCA0fMLa2YrT?= To: "andrew@sterlingcal.com" X-Entity-ID: u001.RuZ2+X9IBGtjUb8qq3teHQ== X-Spam-Status: No, score=-0.6 X-Spam-Score: -5 X-Spam-Bar: / X-Spam-Flag: NO --7e182b9e568533dd2dc140f07069cdcdfd6da9e9c9710d0a1288748a0f79 Content-Transfer-Encoding: quoted-printable Content-Type: text/plain; charset=utf-8 Mime-Version: 1.0 Hello Andrew,=20 **_Funny story_**_, I was in SF last week and brought a few books with me. = On my way back I had two in my bag and thought it=E2=80=99d be funny to lea= ve them in a book store at the airport with a note saying =E2=80=98hey - ta= ke this book, it=E2=80=99s not for sale yet so don=E2=80=99t try to buy it = or the cashier will be super confused=E2=80=99. Well, someone found it and = posted my first review, _[_check it out here_](https://www.linkedin.com/fee= d/update/urn:li:activity:7383548928421695491/)_. If can reshare with your n= etwork, that would be super helpful. _ **_Book update_**_: We hit 235 pre-orders this week, huge shout out to Anth= ony for ordering 5 more for his team! Get your _[_pre-order_](https://www.a= mazon.com/Terrifying-Art-Finding-Customers-Sleep-Deprived/dp/1774586134)_ i= n here if you haven=E2=80=99t already. I just added the Cold Email Delivera= bility Guide and Perfect Call GPT to the pre-order benefits list. _ _**Community update**__: I=E2=80=99ll be in NY on the 31st and am meeting u= p with a few founders for a happy hour, let me know if you=E2=80=99re inter= ested._ _Onto the newsletter=E2=80=A6_ You can't scale what you haven't done yourself. I know, I know. You're thinking, "But I don't have time to be an entry-leve= l employee in my own company." Trust me, I thought the same thing. And that= thinking cost me years of spinning wheels, multiple failed hires, and a pa= inful lesson about the difference between adding features and changing busi= ness models entirely. Let me tell you about the time I tried to pivot our entire service offering= without ever doing the work myself. ## The Business Model Shift That Nearly Broke Us In 2018, we were running Predictable Revenue as a cold email agency. For si= x years, we'd built serious muscle around cold email - we had account strat= egists, proven processes, happy clients. We knew that business inside and o= ut. But we saw the writing on the wall. Cold email reply rates were dropping dr= amatically. Our clients needed more than just email; they needed a full out= bound approach: email + phone + LinkedIn, all integrated into one seamless = process. So we made the call to pivot from a cold email shop to a full SDR outsourci= ng agency. Seemed logical, right? We already had the email piece down. How hard could = it be to just add phone and LinkedIn to the mix? Turns out, I'd made a massive assumption. What felt like adding two channel= s was actually building a completely different business from scratch. ## The False Assumption That Cost Me Everything Here's what I thought was happening: We were taking our existing cold email= service and expanding it. Same basic model, just more touchpoints. Here's what was actually happening: We were building an entirely new busine= ss. Suddenly, we needed to go from having highly skilled account strategists to= people who could be account strategists AND SDR managers. We had to hire, = train, and onboard actual SDRs - something we'd never done at scale. We had= to manage a completely different type of team delivering a completely diff= erent type of service. I totally underestimated the complexity of that transition. So I did what felt smart: I hired a Director of Sales Development. Someone = with serious SDR experience who could inject that expertise into our organi= zation and figure things out. But here's the crucial distinction I missed: They knew SDR work incredibly = well, but they'd never built an SDR service from scratch within an existing= company. Those are two completely different skills. I thought their SDR expertise would combine with our organizational muscle = to create something new. I assumed the people I'd trained over six years co= uld make founder-level decisions like I could. Both assumptions were dead wrong. ## The Four Levels of Work Here's what I learned the hard way. Every function in your business has fou= r levels, here=E2=80=99s an example through the lens of sales development: **Level 1 - IC Work:** Making the calls, sending the emails, using the tool= s daily. Learning objections, discovering messaging, figuring out where pro= cesses break. Most importantly, developing intuition for what "good" looks = like in your specific context. **Level 2 - Management:** Teaching others to replicate what works. Creating= structure, cadence, and accountability. You can only do this effectively i= f you've walked the path yourself. **Level 3 - Leadership:** Hiring and coaching managers, making strategic de= cisions, scaling the system. This requires deep knowledge of what happens a= t Levels 1 and 2. **Level 4 - Executive:** Allocating resources, shaping strategy, driving pe= rformance through metrics and structure. I stayed at Level 4 and hired someone to handle Levels 1-3 simultaneously. = Even worse, I expected them to build something entirely new while operating= at those levels. How could they possibly succeed when I hadn't built the foundation myself? ## What I Should Have Done (But Didn't) The fix is obvious in hindsight, but I was too stubborn to see it: I needed= to do the work myself first. Here's what I should have done from day one: Start at the IC level and work my way up one role at a time. Spend time mak= ing the calls, writing the sequences, learning the tools, mapping objection= s. Actually doing the work within our specific business context, for our sp= ecific clients. Only after I'd figured out what worked could I move to the management level= - hire someone and train them based on what I'd learned. Only after I'd pr= oven I could teach someone else could I move to the leadership level and sc= ale the team. Instead, I tried to skip directly from executive to executive while expecti= ng someone else to build everything in between. I never did go back and walk that path myself. We kept cycling through hire= s, and eventually I shut down that part of the business at the beginning of= this year. It's only in hindsight that I can see the mistakes I made - and= hopefully avoid them next time. ## When to Do the Work Yourself This isn't just about service businesses. This is about founders not diggin= g in and doing the foundational work when they should. Here's the key distinction: Is this a net new capability you're adding to y= our company, or is it an extension of something you already do well? If it's just extending an existing capability - your current team and struc= ture can probably handle it. But if you're building something truly new, yo= u need to start at the IC level. The most common example: building your first sales team. Most founders try = to skip straight to hiring a salesperson to "figure it out" instead of step= ping into the sales IC role themselves first. But you can't hire someone to= build what you haven't built yourself. The only way out is through. You have to step into the IC role and work you= r way up. The pattern is always the same: Start at the IC level, figure out what work= s, then hire someone and train them based on what you learned. Only once yo= u've successfully hired and trained someone can you move yourself up to the= next level. ## The Bottom Line You can't scale what you haven't done yourself - especially when you're bui= lding something new. Great people can't build on a foundation that doesn't exist. They can only = scale what already works; they can't create something from nothing. That so= rt of magic is reserved for founders. Do the IC work first. Build the foundation. Then hire someone great to make= it bigger. So I'll ask you: What foundational work are you trying to skip right now? Collin=C2=A0 PS - I=E2=80=99m making progress in documenting my sales process to turn it= into a set of agents. I found an MCP server for n8n and actually made some= progress on it myself using Windsurf which was super fun. If you=E2=80=99r= e keen to be an early tester and you=E2=80=99re ok recording calls via zoom= , then drop me a note. I may have something in the next month to play with.= =20 PPS - here=E2=80=99s the shot of me being cheeky at SFO=E2=80=A6=20 View image: (https://media.beehiiv.com/cdn-cgi/image/fit=3Dscale-down,forma= t=3Dauto,onerror=3Dredirect,quality=3D80/uploads/asset/file/0aec2f6b-9258-4= 7e7-a115-16f58e60969e/image.png?t=3D1760654355) 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/you-need-to-do-it-yourself-first --7e182b9e568533dd2dc140f07069cdcdfd6da9e9c9710d0a1288748a0f79 Content-Transfer-Encoding: quoted-printable Content-Type: text/html; charset=utf-8 Mime-Version: 1.0 You Need to Do It Yourself First
=
<= 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">

October= 17, 2025   |   Read Online

You= Need to Do It Yourself First

<= /table>
= 3D"share
&nbs= p;
3D"share
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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;">

Funny story, I was in SF last week and brought a few books = with me. On my way back I had two in my bag and thought it=E2=80=99d be fun= ny to leave them in a book store at the airport with a note saying =E2=80= =98hey - take this book, it=E2=80=99s not for sale yet so don=E2=80=99t try= to buy it or the cashier will be super confused=E2=80=99. Well, someone fo= und it and posted my first review, check it out here. If can reshare with your network, that would be sup= er helpful.

= =

Hello Andrew,

= Book update: We hi= t 235 pre-orders this week, huge shout out to Anthony for ordering 5 more f= or his team! Get your = pre-order in here if you haven=E2=80=99t already. I just added the Cold Email Deliv= erability Guide and Perfect Call GPT to the pre-order benefits list.

Community update: I=E2=80=99ll be in= NY on the 31st and am meeting up with a few founders for a happy hour, let= me know if you=E2=80=99re interested.

Onto the newsletter=E2=80=A6

You can't scale what you haven't d= one yourself.

I know, I= know. You're thinking, "But I don't have time to be an entry-= level employee in my own company." Trust me, I thought the same thing.= And that thinking cost me years of spinning wheels, multiple failed hires,= and a painful lesson about the difference between adding features and chan= ging business models entirely.

Let me tell you about the time I tried to pivot our entire service = offering without ever doing the work myself.

The Business Model Shift = That Nearly Broke Us

I= n 2018, we were running Predictable Revenue as a cold email agency. For six= years, we'd built serious muscle around cold email - we had account st= rategists, proven processes, happy clients. We knew that business inside an= d out.

But we saw the w= riting on the wall. Cold email reply rates were dropping dramatically. Our = clients needed more than just email; they needed a full outbound approach: = email + phone + LinkedIn, all integrated into one seamless process.<= /p>

So we made the call to pivot f= rom a cold email shop to a full SDR outsourcing agency.

Seemed logical, right? We already had the = email piece down. How hard could it be to just add phone and LinkedIn to th= e mix?

Turns out, I'= ;d made a massive assumption. What felt like adding two channels was actual= ly building a completely different business from scratch.

The False As= sumption That Cost Me Everything

Here's what I thought was happening: We were taking our exis= ting cold email service and expanding it. Same basic model, just more touch= points.

Here's what= was actually happening: We were building an entirely new business.<= /p>

Suddenly, we needed to go from= having highly skilled account strategists to people who could be account s= trategists AND SDR managers. We had to hire, train, and onboard actual SDRs= - something we'd never done at scale. We had to manage a completely di= fferent type of team delivering a completely different type of service.

I totally underestimated t= he complexity of that transition.

So I did what felt smart: I hired a Director of Sales Developmen= t. Someone with serious SDR experience who could inject that expertise into= our organization and figure things out.

But here's the crucial distinction I missed: They kn= ew SDR work incredibly well, but they'd never built an SDR service from= scratch within an existing company. Those are two completely different ski= lls.

I thought their SD= R expertise would combine with our organizational muscle to create somethin= g new. I assumed the people I'd trained over six years could make found= er-level decisions like I could.

Both assumptions were dead wrong.

<= h2 style=3D"color:#2A2A2A;font-weight:normal;mso-line-height-alt:150.0%;"><= span style=3D"color:rgb(44, 62, 80);">The Four Levels of Work

Here's what I learned the hard = way. Every function in your business has four levels, here=E2=80=99s an exa= mple through the lens of sales development:

Level 1 - IC Work: Making the calls, sending the emails, usi= ng the tools daily. Learning objections, discovering messaging, figuring ou= t where processes break. Most importantly, developing intuition for what &q= uot;good" looks like in your specific context.

Level 2 - Management: Teaching others to replicate w= hat works. Creating structure, cadence, and accountability. You can only do= this effectively if you've walked the path yourself.

Level 3 - Leadership:= Hiring and coaching mana= gers, making strategic decisions, scaling the system. This requires deep kn= owledge of what happens at Levels 1 and 2.

Level 4 - Executive: Allocating resources, shaping strategy, = driving performance through metrics and structure.

I stayed at Level 4 and hired someone to handle= Levels 1-3 simultaneously. Even worse, I expected them to build something = entirely new while operating at those levels.

How could they possibly succeed when I hadn't bu= ilt the foundation myself?

What I Should Have Done (But Didn't)

The fix is obvious in hind= sight, but I was too stubborn to see it: I needed to do the work myself fir= st.

Here's what I s= hould have done from day one:

Start at the IC level and work my way up one role at a time. Spend t= ime making the calls, writing the sequences, learning the tools, mapping ob= jections. Actually doing the work within our specific business context, for= our specific clients.

= Only after I'd figured out what worked could I move to the management l= evel - hire someone and train them based on what I'd learned. Only afte= r I'd proven I could teach someone else could I move to the leadership = level and scale the team.

Instead, I tried to skip directly from executive to executive while expe= cting someone else to build everything in between.

I never did go back and walk that path myself. = We kept cycling through hires, and eventually I shut down that part of the = business at the beginning of this year. It's only in hindsight that I c= an see the mistakes I made - and hopefully avoid them next time.

=

When to Do t= he Work Yourself

Thi= s isn't just about service businesses. This is about founders not diggi= ng in and doing the foundational work when they should.

Here's the key distinction: Is this a = net new capability you're adding to your company, or is it an extension= of something you already do well?

If it's just extending an existing capability - your curren= t team and structure can probably handle it. But if you're building som= ething truly new, you need to start at the IC level.

The most common example: building your first = sales team. Most founders try to skip straight to hiring a salesperson to &= quot;figure it out" instead of stepping into the sales IC role themsel= ves first. But you can't hire someone to build what you haven't bui= lt yourself.

The only = way out is through. You have to step into the IC role and work your way up.=

The pattern is always = the same: Start at the IC level, figure out what works, then hire someone a= nd train them based on what you learned. Only once you've successfully = hired and trained someone can you move yourself up to the next level.

The Bottom Line

You can't scale what y= ou haven't done yourself - especially when you're building somethin= g new.

Great people can= 't build on a foundation that doesn't exist. They can only scale wh= at already works; they can't create something from nothing. That sort o= f magic is reserved for founders.

Do the IC work first. Build the foundation. Then hire someone gr= eat to make it bigger.

= So I'll ask you: What foundational work are you trying to skip right no= w?

Collin=C2=A0<= /p>

PS - I=E2=80=99m making progre= ss in documenting my sales process to turn it into a set of agents. I found= an MCP server for n8n and actually made some progress on it myself using W= indsurf which was super fun. If you=E2=80=99re keen to be an early tester a= nd you=E2=80=99re ok recording calls via zoom, then drop me a note. I may h= ave something in the next month to play with.

PPS - here=E2=80=99s the shot of me being cheeky at= SFO=E2=80=A6

3D""
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