Photography
AI Strategy & Consulting
Let AI Handle the Busywork So You Can Stay Focused on the People
Automations and custom tools for the busywork. Brand and design for everything your customers see. Training and partnership for the long haul.
Somewhere along the way, the business started running you.
The follow-ups. The proposals. The scheduling. The admin that breeds more admin.
You're spending your best hours on work that has nothing to do with why people hire you.
Your clients don't come back because of your systems. They come back because of you. I make sure there’s enough left to give them.
Somewhere along the way, the business started running you.
The follow-ups. The proposals. The scheduling. The admin that breeds more admin.
You're spending your best hours on work that has nothing to do with why people hire you.
You don't need another app.
You need someone who understands your business well enough to know what to hand off, and what to protect.
How I Can Help
Start wherever you need. Learn it yourself, hand it off, or something in between.
Alameda County
Brian introduced me to AI tools and workflows I wouldn't have thought to use. I now have a way forward to execute ideas that have been percolating in my head for years.
Brian introduced me to AI tools and workflows I wouldn't have thought to use. I now have a way forward to execute ideas that have been percolating in my head for years.
MARK DOMBECK
Psychologist & Founder, Psychtools.com
Hear me out...
Should You
Leverage AI?
The answer is an astounding yes. You don't need to know anything to start. Just reach out and I'll show you.
Hear me out...
Should You
Leverage AI?
The answer is an astounding yes. You don't need to know anything to start. Just reach out and I'll show you.
Hear me out...
Should You
Leverage AI?
The answer is an astounding yes. You don't need to know anything to start. Just reach out and I'll show you.
Hear me out...
Should You
Leverage AI?
The answer is an astounding yes. You don't need to know anything to start. Just reach out and I'll show you.
2026
01
Your Time
What if You Could Get 10+ Hours a Week Back?
Most business owners I work with get that back in their first month. AI handles the work that eats your day, and those hours come back to you. Invest them in your business. Invest them in your family. Finally fix that thing that's been broken for six months or read that book finally. Once you learn how to use AI properly, it never stops giving you time back.
In Practice:
New Ventures
The Backlog
Family + Weekends Off
01
Your Time
What if You Could Get 10+ Hours a Week Back?
Most business owners I work with get that back in their first month. AI handles the work that eats your day, and those hours come back to you. Invest them in your business. Invest them in your family. Finally fix that thing that's been broken for six months or read that book finally. Once you learn how to use AI properly, it never stops giving you time back.
In Practice:
New Ventures
The Backlog
Family + Weekends Off
01
Your Time
What if You Could Get 10+ Hours a Week Back?
Most business owners I work with get that back in their first month. AI handles the work that eats your day, and those hours come back to you. Invest them in your business. Invest them in your family. Finally fix that thing that's been broken for six months or read that book finally. Once you learn how to use AI properly, it never stops giving you time back.
In Practice:
New Ventures
The Backlog
Family + Weekends Off
02
Strategy
What if You Had a Team of Strategists on Call 24/7?
A thinking partner for the hard stuff: A pricing consultant when you're undercharging. A mediator when your team's in conflict. A brand strategist when your website doesn't sound like you anymore. A negotiator when a vendor changes terms. Whatever you need, whenever you need it — no retainer, no referral, no waiting. AI doesn't replace your instincts. It sharpens them.
In Practice:
Thinking Partner
Business Coach
On-Call Advisor
02
Strategy
What if You Had a Team of Strategists on Call 24/7?
A thinking partner for the hard stuff: A pricing consultant when you're undercharging. A mediator when your team's in conflict. A brand strategist when your website doesn't sound like you anymore. A negotiator when a vendor changes terms. Whatever you need, whenever you need it — no retainer, no referral, no waiting. AI doesn't replace your instincts. It sharpens them.
In Practice:
Thinking Partner
Business Coach
On-Call Advisor
02
Strategy
What if You Had a Team of Strategists on Call 24/7?
A thinking partner for the hard stuff: A pricing consultant when you're undercharging. A mediator when your team's in conflict. A brand strategist when your website doesn't sound like you anymore. A negotiator when a vendor changes terms. Whatever you need, whenever you need it — no retainer, no referral, no waiting. AI doesn't replace your instincts. It sharpens them.
In Practice:
Thinking Partner
Business Coach
On-Call Advisor
03
Daily Comms
What if All Your Messages Landed Exactly Right?
A tough conversation with an employee, handled with the right tone. A reply to your lawyer that's clear and confident. A proposal or menu adjustment that makes your pricing feel obvious. AI doesn't just help you write, it helps you think through who you're talking to and what the moment requires.
In Practice
Internal + External Comms
Lawyers & Vendors
Sales & Pricing
03
Daily Comms
What if All Your Messages Landed Exactly Right?
A tough conversation with an employee, handled with the right tone. A reply to your lawyer that's clear and confident. A proposal or menu adjustment that makes your pricing feel obvious. AI doesn't just help you write, it helps you think through who you're talking to and what the moment requires.
In Practice
Internal + External Comms
Lawyers & Vendors
Sales & Pricing
03
Daily Comms
What if All Your Messages Landed Exactly Right?
A tough conversation with an employee, handled with the right tone. A reply to your lawyer that's clear and confident. A proposal or menu adjustment that makes your pricing feel obvious. AI doesn't just help you write, it helps you think through who you're talking to and what the moment requires.
In Practice
Internal + External Comms
Lawyers & Vendors
Sales & Pricing
04
Operations
What if You Had a Project Manager for Every Idea?
From kickoff to delivery — AI helps you build living documents that track every detail, keep your team aligned, and give clients the feeling that nothing will fall through the cracks. The kind of organization that used to require a full-time project manager.
In Practice:
Projects & Operations
Start-to-Finish Tracking
Complex Project Management
04
Operations
What if You Had a Project Manager for Every Idea?
From kickoff to delivery — AI helps you build living documents that track every detail, keep your team aligned, and give clients the feeling that nothing will fall through the cracks. The kind of organization that used to require a full-time project manager.
In Practice:
Projects & Operations
Start-to-Finish Tracking
Complex Project Management
04
Operations
What if You Had a Project Manager for Every Idea?
From kickoff to delivery — AI helps you build living documents that track every detail, keep your team aligned, and give clients the feeling that nothing will fall through the cracks. The kind of organization that used to require a full-time project manager.
In Practice:
Projects & Operations
Start-to-Finish Tracking
Complex Project Management
You don't need to be tech savvy. You need someone to show you what's worth your time.
If you've been meaning to figure out AI, but havent known where to start… start here.
BRIAN DESIMONE
Serving San Francisco’s ambitious founders since 2015.
Ai Generated
Questions
Questions
I'll Ask You.
I'll Ask You.
What would you do with 10 extra hours a week?
You'd be surprised how many people pause on this one. They've been so deep in the day-to-day that they've stopped imagining what they'd do with the time. That pause tells me everything I need to know about how much the admin has taken over.
What would you do with 10 extra hours a week?
You'd be surprised how many people pause on this one. They've been so deep in the day-to-day that they've stopped imagining what they'd do with the time. That pause tells me everything I need to know about how much the admin has taken over.
What would you do with 10 extra hours a week?
You'd be surprised how many people pause on this one. They've been so deep in the day-to-day that they've stopped imagining what they'd do with the time. That pause tells me everything I need to know about how much the admin has taken over.
Where does your business break down when you step away?
If taking a week off means things fall through the cracks — missed follow-ups, stalled projects, confused clients — that's not a vacation problem. It's a systems problem. This question shows me exactly where your business is too dependent on you being in every conversation.
Where does your business break down when you step away?
If taking a week off means things fall through the cracks — missed follow-ups, stalled projects, confused clients — that's not a vacation problem. It's a systems problem. This question shows me exactly where your business is too dependent on you being in every conversation.
Where does your business break down when you step away?
If taking a week off means things fall through the cracks — missed follow-ups, stalled projects, confused clients — that's not a vacation problem. It's a systems problem. This question shows me exactly where your business is too dependent on you being in every conversation.
What's the idea you keep almost starting?
This is the one that gets people talking. It's always something they're excited about but can never prioritize over the day-to-day. AI is really good at helping you go from "I've been thinking about this for a year" to "here's the plan, let's move."
What's the idea you keep almost starting?
This is the one that gets people talking. It's always something they're excited about but can never prioritize over the day-to-day. AI is really good at helping you go from "I've been thinking about this for a year" to "here's the plan, let's move."
What's the idea you keep almost starting?
This is the one that gets people talking. It's always something they're excited about but can never prioritize over the day-to-day. AI is really good at helping you go from "I've been thinking about this for a year" to "here's the plan, let's move."
What would your business look like if you only did the work you're best at?
This is the real question underneath all the others. Everything we do together is pointed at this — clearing out the work that anyone could do so you can focus on the work that only you can do. Most people light up when they start to see what that actually looks like.
What would your business look like if you only did the work you're best at?
This is the real question underneath all the others. Everything we do together is pointed at this — clearing out the work that anyone could do so you can focus on the work that only you can do. Most people light up when they start to see what that actually looks like.
What would your business look like if you only did the work you're best at?
This is the real question underneath all the others. Everything we do together is pointed at this — clearing out the work that anyone could do so you can focus on the work that only you can do. Most people light up when they start to see what that actually looks like.
© Damn your hair looks good today!
About
Brian DeSimone is an Oakland-based portrait photographer serving San Francisco, Silicon Valley, and the Bay Area.
Specializing in executive headshots, founder portraits, corporate team photography, and editorial brand campaigns for startups, leaders, and creative businesses.
❤️
Studio
© Damn your hair looks good today!
About
Brian DeSimone is an Oakland-based portrait photographer serving San Francisco, Silicon Valley, and the Bay Area.
Specializing in executive headshots, founder portraits, corporate team photography, and editorial brand campaigns for startups, leaders, and creative businesses.
❤️
Studio
© Damn your hair looks good today!
About
Brian DeSimone is an Oakland-based portrait photographer serving San Francisco, Silicon Valley, and the Bay Area.
Specializing in executive headshots, founder portraits, corporate team photography, and editorial brand campaigns for startups, leaders, and creative businesses.
❤️