Founder Playbook · The Bootstrapped Founder
13 tactics from Brennan Dunn
Brennan Dunn — This Is Personal
Watch the full episode“I'm very used to like iterative building and kind of this idea that you never actually finish anything... this whole idea of like it's a bit like I guess like making a movie where once it's done it's done”
Match shipping cadence to the medium
Book publishing is the inverse of SaaS — no A/B tests, no iteration, no immediate feedback loop. Budget for a multi-year process you can't tweak post-launch, and accept that the audience will be unpredictably broad. If you need the dopamine of weekly shipping, books will frustrate you. Pick the right cadence per medium instead of fighting it.
“Early on the idea is before you spend a ton of time on a sales page or marketing website you should get on calls and do demos and so on and so forth, and that's kind of the conventional wisdom right, like you should learn as much as you can from your audience”
Run sales-style demos before scaling marketing pages
Skip the polished marketing site at first. Hop on one-to-one calls, listen for the objections that actually surface, and learn which benefits land with which type of buyer. That direct sales context becomes the raw material for every segment and conditional block you build later in your funnel.
“Even if I don't do anything with that data I think it's important to have that information... I started doing that when I did Create and Sell and launched it to the world at first, immediately I was segmenting but I wasn't doing anything with that data”
Segment at opt-in even if you do nothing with the data
Bake two segmentation questions into your opt-in from launch day — even before you're ready to act on them. It's brutally hard to retrofit identity data onto an existing 50K-subscriber list; far easier to ask each new subscriber on day one. The first job of the data is market research on your own audience; conditional emails come later.
“across the board we're seeing between an 80 to 85 response rate so completion rate of the surveys for new subscribers when doing that... they make it clear this is not just like market research data... we're getting this information so I can better serve you”
Frame surveys as "to serve you" for 80% completion
Position the post-signup survey as "so I can better serve you" — never as research. Keep questions to one-tap multiple choice, promise 15-20 seconds, and you'll consistently see 80-85% completion across audiences of all sizes. Position trumps every other survey-design lever.
“I prefer one of many... it's more work to fill in a text field than it is to click a button and on top of that if it's like which of the following do you like red green or blue if they choose red it's very easy for you to then say hey if they chose red make the background red”
Force multiple choice — never free text
Multi-choice buttons drive 98-99% click-through to the next question because there's zero cognitive load and the answers are machine-readable for downstream personalization. Free-text input collapses both completion AND your ability to use the data. Use an "Other" with a free-text follow-up only as a release valve, then mine those entries to rephrase existing buttons later.
“at a minimum you should be uncovering two things one of which is why they're currently interested in what you have to offer... and then a who question is so the who for me is what email platform you use and how would you self-assess your experience with it”
Ask one outcome question and one identity question
Keep the post-signup survey to two essentials: one outcome question (what are you trying to achieve?) and one identity/tool question (what's your stack, what's your experience level?). That pairing tells you who's showing up, what content they need, and which product gaps to fill next — without survey fatigue.
“convert to people for me are worth about eighty dollars per subscriber but somebody on active campaign is worth about like five right so I that tells me like either converted people have a lot more disposable income and they really like what I'm doing versus active campaign or I'm dropping the ball with them”
Measure subscriber value by attribute to find product gaps
Wire your ESP + Stripe data into a tool like SegMetrics so you can break average subscriber value down by every survey attribute. A 16x value gap between two segments (ConvertKit $80 vs ActiveCampaign $5) is a flashing sign of a missing product, not a coincidence — Brennan's new beginner segmentation course came directly from spotting exactly this gap.
“I've recently kind of started doing consulting again with this little agency thing and um we've been doing pretty much for all of our clients setting up segmentation survey funnels”
Spin up an agency arm on top of your SaaS
Run a small agency that delivers your SaaS's playbook done-for-you to high-leverage clients (Pat Flynn, Justin Welsh). You get statistically significant data from their giant lists, social proof from name-brand creators, and the agency cash funds product R&D. The SaaS and the agency compound each other in ways the SaaS alone cannot.
“we just do a simple broadcast that goes out to the list and says hey we want to make like we're working on the next kind of like our future content calendar and we want to make sure that what we're creating aligns with you and your needs what do you remind or would you mind replying to this email with one or two sentences”
Validate audience with one broadcast reply email
If you have no idea who's actually on your list, send one plain-text broadcast asking for a one-or-two-sentence reply about who they are and what they want. Normalize the top three or four themes into a V1 segmentation, ignore the outliers, and ship. This is the cheapest audience research in existence and takes one hour.
“what if we could then dynamically Niche so instead it's like they are getting a email that I send about the course and then if they're a Creator maybe I put the quote from Dickey push of ship 30 because he's a Creator and if they are a consultant maybe I put the quote from... they've used their clients to like make to basically they've taken what I've taught them and built a really good little personal freelancing or agency business”
Dynamically niche by swapping testimonials, not pages
Niching always wins, but running "Mastering ConvertKit for SaaS" AND "...for Book Authors" AND "...for Consultants" is insane. Keep one product page/email and conditionally swap the testimonial, case study, or single benefit paragraph based on what the visitor told you. Cheapest form of dynamic niching, and it's why generic "works for everyone" copy converts worse than either targeted version.
“I look at it as the middle ground between what most of us are doing now which is basically online brochures where you have like your website which is like a brochure it's like the same thing for everyone... I call it like billboard kind of marketing it's the middle ground between that and what you would do if you picked up the phone”
Position marketing between billboard and phone call
Most founder websites are billboards — one message, identical for every visitor, lands with no one specifically. A sales call is the opposite extreme — perfectly tailored but caps at one human per hour. Personalized marketing splits the difference: write the page or email as if you were on the phone with the segment you already know they belong to, with if/else logic doing the heavy lifting.
“what queer bit reveal in in platforms like that allow you to do where given an IP address it will say we think they work at IBM and then like a little pop-up will show up like a chat driftbot saying Hey ibmer or something like that to me is... where it gets a little creepy”
Listen, don't enrich — citation is the creepy-line
The line between helpful and creepy is whether you name where the data came from. Personalization based on volunteered data ("you told me you work with a team, so here's why this fits") feels like listening; personalization based on inferred data (IP→company, scraped LinkedIn, wrong first name) feels invasive and breaks trust the moment it's wrong. Cite the source explicitly: "you shared this with me" beats every black-box inference.
“it's not about being Coy it's not about being it's just about like again like showing that you're listening and saying I'm listening and here's a different set of bullet points for you that I think are going to really resonate with you”
Open personalized copy with "you shared with me"
Open every personalized block with explicit attribution — "you shared with me that you work with a team, so here's why this gets you to the next level" — instead of silently injecting inferred facts. Pat Flynn's Black Friday A/B test using exactly this "you fit this profile, here's why" framing was 2.38x more performant than the generic everything-on-offer control.