Ben Fisher✨

Founder @ Rodeo and Fractional CTO to 8-figure DTC brands, sharing learnings as a Full-stack Coder, Designer and Shopify Expert

My friend Paul says I'm a "Human Zapier." That checks out. 

I'm a solid programmer and a decent designer, but they're really a means to an end: I love to build things and solve business problems. 

I'm a product person, a technologist, and an entrepreneur at heart. 

My superpower is at the intersection of tech + design + automation/optimization. And I love dtc ecomm.

I get a DISGUSTING amount of satisfaction by eliminating inefficiency. And I do it through building software tools.

I am obsessed with Systems Thinking and love to experiment with new ways to connect disparate systems.

I won't stop until we've got a deceptively simple solution that's damn fun to use.

**

For the past 10 years, I've built "commerce enablement" tools in the Shopify ecosystem that help DTC brands make more $$$.

With CartHook, we brought post-purchase upsells to the Shopify ecosystem and worked directly w/ Shopify to add it natively. 

CartHook processed > $1B GMV and added $250MM/year in revenue through its post-purchase upsell tech. It was acquired by Pantastic in 2022.

At Rodeo, we released one of the first native Shopify subscription apps (acquired by Recharge) and pivoted to a LTV Growth platform that originated as a small feature. Ultimately, wound it down as Shopify actively started building a solution themselves.

I'm on a mission to build damn good tools that help you make more money and have fun doing it.

Co-founder, Technical CEO

CEOs trying to get their teams using AI — this might be the problem.

Most AI conversations go sideways in the first message.

Not always because people are "bad at prompting" – but because they're thinking out loud. Half-formed ideas, missing context, vague asks. The AI takes that initial direction and runs with it. Now you're course-correcting for the next 10 messages.

For people who steer AI all day, that's fine. You recover and keep going.

But when someone on your team tries AI once, gets garbage, and decides "it doesn't work for me" — that's expensive. And often, it's just a bad first message.

I built Promptó to fix the 𝗳𝗶𝗿𝘀𝘁-𝗺𝗲𝘀𝘀𝗮𝗴𝗲 𝗽𝗿𝗼𝗯𝗹𝗲𝗺.

It's a desktop app – one shortcut from anywhere. Copy your rough thought, press the key, and it turns your half-baked idea into a clear starting point. Then you paste it into ChatGPT, Claude, whatever you use.

What it actually does:

- Asks clarifying questions when you're too vague
- Adds the structure AI needs to run useful
- Saves your context window for actual work, not course-correction

The reason it's a desktop app (not a browser tab): 𝗳𝗿𝗶𝗰𝘁𝗶𝗼𝗻 𝗸𝗶𝗹𝗹𝘀 𝗮𝗱𝗼𝗽𝘁𝗶𝗼𝗻. A shortcut becomes muscle memory. People use it for everything, not just "important" prompts.

The compound effect of starting clean – hundreds of times a week – is real.

One early user told me it writes better prompts for his vertical than his best employees.

If your team has quietly decided AI "isn't for them," it might just be a first-message problem.

𝗜𝘁'𝘀 𝗳𝗿𝗲𝗲 𝗳𝗼𝗿 𝗻𝗼𝘄. Link in the first comment.

Struggling with AI adoption on your team? What's worked (or hasn't)?

--

Link: https://tryprompto.com

Its companion desktop app: https://lnkd.in/ePSw5UHS

Ben Fisher 🏴‍☠️

Playing w/ AI + Automation | Prev @Rodeo, @CartHook (trusted by AG1, Four Sigmatic)

graphical user interface, text, application

Founders / PMs: stop me when this sounds familiar.

You have a great product call. Ideas, constraints, edge cases all get talked through. Everyone hangs up and... nothing really happens.

A week later you're trying to recreate what you already figured out on that call.

Last week I had a 45-minute product brainstorm with my friend Jared Cocken. By the time I closed Claude, I had:

- A first-draft spec the team could actually build from
- User stories mapped to the core problem
- A short list of questions we hadn't answered yet

Total time after the call: ~15 minutes.

In my setup, AI does the boring part:

- Pulling the relevant parts of the conversation out of the call notes
- Turning messy ideas into something an engineer can react to
- Pointing out gaps and edge cases I didn't cover

I still keep the actual thinking:

- Is this even a problem worth solving right now?
- Which requirements are real vs "nice to have"?
- What actually makes it into the doc we share?

Most teams just let transcripts pile up in whatever tool they're using and tell themselves they'll "get to it later."

In practice, later rarely happens.

This little workflow has made it way more likely that good calls turn into actual work instead of just... more recordings.

If you want to see exactly how I run this, I recorded a short "Dear Ben" episode walking through the flow step by step, plus a small Claude skill + GitHub repo you can hand to your team.

(Link in first comment)

--

Show notes & grab the Claude skill: https://lnkd.in/emJ8AbjQ

𝗦𝘁𝗼𝗽 𝘀𝗲𝗻𝗱𝗶𝗻𝗴 (𝗷𝘂𝘀𝘁) 𝘀𝗰𝗵𝗲𝗱𝘂𝗹𝗶𝗻𝗴 𝗹𝗶𝗻𝗸𝘀.

They feel efficient. They're actually kind of rude.

"Here's my calendar. You do the work."

Open link → load page → scroll days → do timezone math → fill the form. All the friction is on the other person.

The most respectful thing you can do instead:

- Propose specific times
- In 𝘁𝗵𝗲𝗶𝗿 timezone
- With a backup link if nothing works

Something like:

> Would any of these times work for a 25 min meeting (ET)?
> • Wed, Jan 7: 10:30am, 10:30am, 1:00pm
> • Thu, Jan 8: 1:00pm, 3:00pm, 3:30pm
> • Fri, Jan 9: 7:00am, 9:00am, 10:30am

> If none of these work, here's my full calendar: [link]

Doing this manually every time sucks:
check calendar → convert timezones → format nicely.

Even premium tools miss this. 

Superhuman has a built-in scheduler, but you still have to *manually* select your available slots. Every. Single. Time. 

I thought AI agents might solve this, but they got timezone conversions wrong or inconsistently replied.

So I did what I usually do with this kind of annoyance:
I built a small tool for myself.

- Raycast extension that pulls from SavvyCal or Cal dot com
- You pick the recipient's timezone
- It batches times around your existing meetings—not random scattered slots & respects your scheduling preferences (buffer times, working hours, etc.)
- Each time is a clickable link to book  

Both are open source.

Same pattern as Promptó for me: build something I genuinely rely on in my own workflow, then see if it quietly becomes indispensable for other people too.

This one just attacks a very specific kind of friction: making other people do the work to meet with you.

👉 (See link in first comment)

Curious: how are you making scheduling less painful for the people you work with?

--

- "Propose Times" — Raycast extension (https://lnkd.in/eVSrzFrp)

- "SavvyCal Booker" — one-click booking form (for Cal.com or SavvyCal) https://lnkd.in/e5P-AVqb

Everyone's hyped about how fast AI can ship features.

Almost no one is talking about the fights it's causing inside engineering teams.

I had two conversations last week with CEOs trying to get their teams to adopt AI. Same pattern both times.

The CEO discovered vibe coding. Built a feature themselves — maybe a proof of concept, maybe a working prototype. Felt the speed. Got excited.

Came back to the team with, "We should all be doing this."

And hit a wall.

Here's what I've realized: the engineers pushing back aren't all pushing back for the same reasons.

I'm seeing two camps:

𝗠𝗮𝗸𝗲𝗿𝘀 — product-oriented. They care about what gets shipped. AI is leverage. Less boilerplate, more interesting problems. They're often already experimenting. (That's me.)

𝗔𝗿𝘁𝗶𝘀𝗮𝗻𝘀 — craft-oriented. They love writing code. The problem-solving, the shaping, the control. They'll happily spend an afternoon refactoring a module no one else will ever see, because the code "wasn't right." AI doesn't just change how they work — it threatens something they've built their whole career around.

The artisan isn't wrong. They're assessing AI through a different lens. And as a leader, you need to recognize: adopting AI might mean giving up parts of the job they genuinely love.

What I've seen work:

𝗙𝗼𝗿 𝗮𝗿𝘁𝗶𝘀𝗮𝗻𝘀 — don't lead with "look how fast it codes." They've seen the output. They're not impressed. Start with workflows that protect the craft: scaffolding, guardrails, and reviews that produce code they'd actually be proud to ship.

𝗙𝗼𝗿 𝗺𝗮𝗸𝗲𝗿𝘀 — they might need the opposite. Coaching on product thinking, not just AI enthusiasm. Sometimes they're over-indexed on the tooling.

The starting point is the same: stop selling AI as a productivity tool. Start by understanding what each person stands to lose — and what they might actually gain.

Which camp are you in? And if you're leading both, what's actually working (or not) on your team?

𝗦𝘁𝗼𝗽 𝘀𝗲𝗻𝗱𝗶𝗻𝗴 𝘀𝗰𝗵𝗲𝗱𝘂𝗹𝗶𝗻𝗴 𝗹𝗶𝗻𝗸𝘀.

They feel efficient. They're actually kind of rude.

"Here's my calendar. You do the work."

Open link → load page → scroll days → do timezone math → fill the form. All the friction is on the other person.

The most respectful thing you can do instead:

- Propose specific times
- In 𝘁𝗵𝗲𝗶𝗿 timezone
- With a backup link if nothing works

Something like:

> Here are a few options that should work on your end:
> • Tues, Jan 14 – 10:00–10:30am your time
> • Wed, Jan 15 – 1:30–2:00pm your time
> • Thurs, Jan 16 – 4:00–4:30pm your time
> If none of these work, here's my full calendar: [link]

Doing this manually every time sucks:
check calendar → convert timezones → format nicely.

𝗘𝘃𝗲𝗻 𝗽𝗿𝗲𝗺𝗶𝘂𝗺 𝘁𝗼𝗼𝗹𝘀 𝗺𝗶𝘀𝘀 𝘁𝗵𝗶𝘀. Superhuman Mail has a built-in scheduler, but you still have to manually pick your available slots every single time. No memory, no defaults. It's just a slightly faster version of the same repetitive work.

I thought AI agents might solve this. Tested three: Howie, Fyxer, and a custom Lindy agent. None of them nailed it. They either got timezone conversions wrong, inconsistently replied, or made the back-and-forth longer instead of shorter.

𝗔𝗻𝗱 𝗲𝘃𝗲𝗻 𝘄𝗵𝗲𝗻 𝘁𝗵𝗲𝘆 𝘄𝗼𝗿𝗸, 𝘁𝗵𝗲𝘆 𝗼𝗻𝗹𝘆 𝗺𝗮𝗸𝗲 𝗶𝘁 𝗲𝗮𝘀𝗶𝗲𝗿 𝗳𝗼𝗿 *𝗺𝗲*. The other person still gets a link. Still has to check their calendar, do timezone math, fill out a form. The friction just moved—it didn't disappear.

So I did what I usually do with this kind of annoyance:
I built a small tool for myself, then opened it up.

So I did what I usually do with this kind of annoyance:
I built a small tool for myself, then opened it up.

- Raycast extension that pulls from SavvyCal or Cal dot com
- You pick the recipient's timezone
- It spits out a preformatted message with a few options
- Each time is a clickable link—there's an optional Vercel app that pre-fills the time slot (neither SavvyCal nor Cal dot com support that natively)

Both are open source:

- Propose Times (Raycast extension)
- SavvyCal-Booker (optional one-click booking form)

Same pattern as Promptó for me: build something I genuinely rely on in my own workflow, then see if it quietly becomes indispensable for other people too.

This one just attacks a very specific kind of friction: making other people do the work to meet with you.

👉 (See link in first comment)

Curious: how are you making scheduling less painful for the people you work with?

Ex-VC of early stage startups. Then founded FounderProject, a venture fund run by students investing in student startups. 

The problem? The fund didn’t materialize as I’d hoped, and that hit hard. 

Yet, amidst the disappointment there was real impact. Hundreds of startups took flight, thousands of startup jobs were created, and the VC world took notice.

It became clear to me: while the right funding matters, the right talent can make or break a startup. That insight led me to create StackedSP, a talent firm for venture backed startups.

Fast forward a decade, StackedSP has helped founders and their startups hire thousands - from founding employees, to leaders. Today, those startups are industry leaders and have raised billions from top investors.

But it's not just about the hires. I actively invest in tech startups, and am a limited partner in venture funds. And, building community is crucial. 

Enter Unstacked Startups – a hub for startup founders and talent. There's a podcast, live events, and a newsletter called FounderMail.

My mission? Empower founders, and startups to build a better future.

Ilan Saks

One of the privileges of running a talent firm focused on venture-backed startups is that you sit at an interesting intersection.

You talk to founders about who they need. You talk to investors about what they're funding. You talk to operators about where they want to go next.

This week we brought 15 of those people into a room together.

No decks or agendas. Just drinks and honest conversation about what's actually working, especially around AI.

What stood out: the knowledge wasn't siloed. Someone shared their AI stack. Someone else asked how they set it up. 20 minutes later they're huddled in a corner still going.

That's the thing about small rooms with the right people, the learning compounds in ways that don't happen at big events with name tags.

This is what Unstacked Startups is becoming: a community where founders, investors, and the best talent in tech actually know each other.

Not through LinkedIn. Through rooms like this.

DM me if you want in.

Unstacked Startups & StackedSP | Backing founders & helping them hire elite talent ⚡

"I want to be one of the first two calls when the CEO is facing a hard moment."
- Chris Arsenault, Co-Founder of Inovia Capital

This is what true partnership looks like.

Not quarterly board meetings, or strategic advice when things are going well.

But being the person founders call when:
- They just lost their biggest customer
- There's a co-founder conflict
- An acquisition offer is on the table
- They need to soundboard in real-time

Chris measures success by this metric, and founders who have someone like this in their corner are miles ahead.

Throwback to the full episode with Chris on Optionality, AI, and Talent: https://lnkd.in/d9-fgrZh

What's the hard moment where you'd want someone in your corner?

"If you're hiring a VP of Engineering or CTO, what makes them valuable?"

Khang Tran's answer surprised me.

Khang built engineering teams at Uber, scaled teams at Sonder and HipCamp, and continues to build Eng teams at top startups.

His take on what separates great engineering leaders:

"It's not that they can code really well. It's not that they're really great at architecture."

"It's really about: can this person build a great team"

He breaks it down: 

- Do you know how to hire? 
- Can you close the candidates you want? 
- Can you do tons of interviews and spot the best? 
- Can you make the hard calls when someone isn't working out? 
- Can you build culture and figure out comp?

Technical brilliance and team-building are different muscles.

I've seen 10x engineers struggle to build a team of 3.

And I've seen leaders who haven’t coded much in years build high-performing eng teams.

The best do both. But if I had to pick one for a leadership role? I'm betting on the builder.

🎬 Hit play, Khang explains it better than I can.

#UnstackedPod #StackedSP #EngineeringLeadership

Stop hiring specialists.

That's the counterintuitive advice from Andy Sen, CTO of unicorn AppDirect, who's spent years scaling engineering teams globally.

He's seeing something shift in real-time:

"AI is bringing about a resurgence of generalists. We're already at the point where somebody who's not a specialist, using an AI tool, can design something, build it, and have a finished product out there."

The old model: 5 specialists on one team.
The new model: 5 teams of generalists with specialists jumping in to "polish."

Andy calls this becoming more "talent fluid" — engineers who can shape-shift across backend, frontend, product thinking.

We are also seeing this shift at StackedSP. The best early-stage hires right now aren't the deepest experts. They're the curious generalists who can wield AI as a force multiplier.

What's more valuable to your team right now — depth or adaptability?

🎧 Full conversation on the Unstacked Startups podcast: https://lnkd.in/dy7yhJfD

#UnstackedPod #StackedSP #HighAgency #10xTalent #AIinHiring

Most founders underestimate how early talent decisions compound.

Great founders don’t treat hiring as a checklist.
They treat it as infrastructure.

Whether it’s a VP of Engineering or the first non-technical hire every person shapes:
• culture
• standards
• velocity
• future hiring quality

Early teams don’t just execute work, they define what “good” looks like for everyone who joins next.

This is why “we’ll fix hiring later” is one of the most expensive lies in startups.

Check out Foundermail for more on how to get early hiring right: https://lnkd.in/gbVjDQVB

#startuptalent #earlyhiring

Many founders obsess over ideas.

The best ones obsess over people.

Every breakout company I’ve seen had:
• A founder who could recruit talent before traction
• Early hires who were operators, not passengers
• A culture that filtered out low-agency behaviour fast

Ideas pivot.
Markets shift.
Talent compounds.

If you’re struggling to hire right now, it’s usually not a sourcing problem.

It’s a clarity problem.

Do you actually know:
- what “great” looks like in this role?
- why a top 1% person would join you?
- what this hire unlocks 12 months from now?

Most hiring stalls not because founders can’t find talent 
but because they can’t clearly articulate why the right person should care.

Clarity attracts talent.

Check out the latest edition of Foundermail for more startup talent related insight.

Open article: FounderMail #17 Edition: Your Only Early Stage Moat by foundermail.substack.com

FounderMail #17 Edition: Your Only Early Stage Moat

One line from my conversation with Andy Sen that stood out: 

"Your company's strategy is downstream from your culture."

After 16 years as CTO at AppDirect, Andy's seen teams scale from 3 people in one room to 1,000+ across the globe.

His take on AI and talent:

We're witnessing the resurgence of the generalist. Instead of 5 specialists on one team, Andy sees a future of 5 generalist-led teams with specialists jumping in to "polish" the work.

He called it being "talent fluid"... the ability to shape-shift and adapt.

Thanks Andy for the conversation and for always keeping the bar high. It was great catching up after all these years.

🎧 Full episode link below
#UnstackedPod #StackedSP #HighAgency #10xTalent

AI isn’t replacing strategy - it’s reshaping how teams think, build, and solve problems.

In this episode, Ilan Saks sits down with Andy Sen, CTO of AppDirect, to unpack lessons from years in e-commerce, remote team building, and leading through rapid change. From why culture drives strategy to how AI is bringing back the generalist, this conversation is a grounded look at leadership in an evolving talent landscape.

Listen now and explore what it really takes to build adaptable, future-ready teams.

https://lnkd.in/eE5xw7gM

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The Battle

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Engagements

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