Startup Advising

The technical calls and pivot moments that determine whether your startup scales or stalls. Guidance from someone who ships products, not just advises on them.

What’s included

Honest answers to the questions you can’t ask anyone else. Technical decisions, scaling calls, and pivot moments with someone who’s sat in your seat and made the same calls.

Sounding board

Architecture, infrastructure, and build-or-buy decisions with someone who’s made them.

Scaling guidance

When to hire, when to outsource, and how to grow without outpacing your runway.

Pivot clarity

Sharp assessment when the original plan isn’t working and the clock is ticking.

Hands-on building

When advice isn’t enough, we roll up our sleeves and build alongside you.

The hardest conversations I have with founders aren’t about technology. They’re about the thing they haven’t said out loud yet. Once it’s on the table, we can actually work with it.

Justin Sisley

Justin Sisley

Founder, Peppercrest

How it works

From tough calls to clear direction

01

Understand your situation

We learn what you’re building and what’s keeping you up at night. No pitch. Just a conversation.

02

Work the hard calls

Regular sessions focused on the decisions that matter most. Technical architecture, hiring, product direction, runway.

03

Grow the relationship

As your needs change, advisory expands into hands-on building. Same person, same standard, no vendor search.

At a glance

Measurable impact

Startup decisions don’t get easier, but they get clearer when you have someone in your corner who’s faced similar situations and knows where the landmines are.

Operator advisory

Guidance from someone who builds products, not just advises on them

One seat, full stack

Technical, product, and business decisions without assembling a committee

Built for

Built for founders in the thick of it

Scaling fast

You raised capital and need to build. Every technical decision compounds.

Facing a pivot

The original plan isn’t working and the runway is burning.

Technical founder

You can build anything but need a strategic sounding board for the business side.

Non-technical founder

You have the vision but need a technical co-pilot you can be honest with.

FAQ

Common questions

What to expect from a Startup Advising relationship.

Get started

Let’s talk about what you’re building

Tell us where you are and what’s in front of you. If our experience is relevant, you’ll know in the first conversation. If it’s not, we’ll tell you.

  • Tell us what you’re building and what’s in front of you
  • We’ll assess fit and propose how to work together
  • Kick off with a session on your hardest problem

How we work

See our approach and process from strategy to shipped.

Playbooks

Explore our guides and frameworks for founders building with AI.

Your next hard call doesn’t have to be solo

Tell us what you’re building. If we can help, you’ll know in the first conversation.