Taylor Doolittle sells 50+ homes a year, co-leads an 18-agent team, and builds his week around his family first. He speaks on the systems and decisions that make that possible.
Topics
Each talk comes from how Taylor runs his own business today.
Best for: producing agents and sales meetings
Taylor puts family, health, and faith on the calendar first. The business gets fit around them. This talk walks through how that works at 50+ closings a year, and what has to be in place before you can try it yourself.
Best for: solo agents doing 15+ deals
When to hire an assistant, what to hand off first, and how to keep good help around for years. Taylor's full-time assistant has been with him for five years.
Best for: team leads and growing agents
Most agents keep the repeatable parts of the business in their head. This talk is about getting them out and into systems your team can run on the days you're not there. Taylor wrote down what worked from his first year in the business, and those notes became the playbook Team Steady runs on.
Taylor also trains agents and brokerages on using AI for the admin, follow-up, and prep in their week. Those sessions, including the KEYTalks session at RE/MAX Results, have their own page on the AI Agent Academy site.
See the AI sessions (opens in a new tab)Formats
Good for a sales meeting or a brokerage with agents in several offices.
Taylor presents in person at your office or sales meeting, with time for agents to bring their own questions.
A keynote or breakout for an association, conference, or company event. It works for a mixed room, from newer agents to team leads.
Recent sessions
KEYTalks at RE/MAX Results
Edina, MN · 125+ attendees
ERA Donahoe
Zoom training for 30+ agents
Both of these were AI sessions. The talks on systems, hiring, and family-first scheduling are new.
For event organizers
Copy these straight into your program or hand the intro to your emcee.
Short bio
Taylor Doolittle is a real estate agent with RE/MAX Results in the Twin Cities. He closed 52 transactions in 2025 and has more than 550 career sales. He co-founded Team Steady with Sam Steadman and Lars Anderson and has co-led it since 2017. Today it's an 18-agent team. Taylor builds his week around his family first, and the business fits into the time that's left. Before real estate, he was a technology trainer at Apple. He also founded AI Agent Academy, an AI training program for residential agents.
Emcee introduction
Our next speaker closed 52 transactions in 2025 and co-leads an 18-agent team. He also plans his calendar around his family before his business. He's here to show you how he does it. Please welcome Taylor Doolittle.
FAQ
Yes. Zoom works well for sales meetings and for brokerages with agents spread across several offices.
Residential agents and the people who lead them. The family and first-hire talks fit producing agents. The systems talk is aimed at team leads and agents who are starting to grow.
Yes. Tell Taylor who will be in the room and what they're working on, and he'll shape the session around that.
Book a 30-minute intro call, or email taylor@ts-re.com with your date, location, and roughly how many agents will attend.
That depends on the format and location. Send the details and Taylor will follow up.
The Twin Cities, Minnesota. Zoom sessions work from anywhere. For in-person dates outside Minnesota, reach out with the details.
Yes. Taylor also trains agents and brokerages on AI. Those sessions are listed at theaiagent.academy/speaking.
Send the date, the format, and roughly how many agents will be in the room. Taylor will reply with what he'd cover.
