Ep. #70 | Systems, Partnerships, and the Power Couple Playbook With Tony and Ashley Eisenhauer
Tue Feb 03 2026
In this episode of The Long Game, Ryan Richards sits down with Tony and Ashley Eisenhauer, a real estate power couple based in Northern Connecticut who are scaling fast across multiple ventures, from fix and flips and long-term rentals to short-term rentals and home staging.
This conversation is all about what changes when you stop thinking like a worker and start thinking like an operator. Tony and Ashley break down the systems mindset behind building more without burning out, including how they buy back their time, build the right team, and make strategic decisions that compound over years, not weeks.
They also unpack the real-world lessons from launching a high-performing Airbnb in North Conway, New Hampshire, why design and amenities matter more than most investors realize, and how they think about mentoring others through the entire STR launch process from market analysis to execution.
Ryan and the Eisenhauers dive into creative finance, community, and purpose, including how they frame goals around impact first and income second, and what it looks like to build a business and a life with aligned values.
What you’ll learn:
The systems mindset behind scaling multiple businesses at onceWhy buying back your time is a business strategy, not a luxuryHow Tony forced a role shift by removing “busy work” from his lifeWhat separates high-performing short-term rentals from “just another listing”How they use market data to choose amenities that drive higher revenueThe difference between visionaries and integrators when choosing business partnersWhy community is a cheat code for growth in real estate and entrepreneurshipA practical way to start building systems without getting stuck in analysis paralysisHow creative finance strategies can unlock faster scaling when you know your numbers
GUEST INFO:
Instagram | @tonyeisenhower @ash_eisenhauerYouTube | @tonyeisenhauerInterested in connecting?
HOST
Ryan Richards | Branch Manager, Northpoint Mortgage | NMLS 1987735
rrichards@trynorthpoint.com | www.financewithteamrichards.com
204 Turnpike Rd, Westborough, MA 01581
Licensed in MA, CT, FL, NC, NH, PA, RI
Follow us on Instagram @financewithteamrichards @the.longgamepodcast
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In this episode of The Long Game, Ryan Richards sits down with Tony and Ashley Eisenhauer, a real estate power couple based in Northern Connecticut who are scaling fast across multiple ventures, from fix and flips and long-term rentals to short-term rentals and home staging. This conversation is all about what changes when you stop thinking like a worker and start thinking like an operator. Tony and Ashley break down the systems mindset behind building more without burning out, including how they buy back their time, build the right team, and make strategic decisions that compound over years, not weeks. They also unpack the real-world lessons from launching a high-performing Airbnb in North Conway, New Hampshire, why design and amenities matter more than most investors realize, and how they think about mentoring others through the entire STR launch process from market analysis to execution. Ryan and the Eisenhauers dive into creative finance, community, and purpose, including how they frame goals around impact first and income second, and what it looks like to build a business and a life with aligned values. What you’ll learn: The systems mindset behind scaling multiple businesses at onceWhy buying back your time is a business strategy, not a luxuryHow Tony forced a role shift by removing “busy work” from his lifeWhat separates high-performing short-term rentals from “just another listing”How they use market data to choose amenities that drive higher revenueThe difference between visionaries and integrators when choosing business partnersWhy community is a cheat code for growth in real estate and entrepreneurshipA practical way to start building systems without getting stuck in analysis paralysisHow creative finance strategies can unlock faster scaling when you know your numbers GUEST INFO: Instagram | @tonyeisenhower @ash_eisenhauerYouTube | @tonyeisenhauerInterested in connecting? HOST Ryan Richards | Branch Manager, Northpoint Mortgage | NMLS 1987735 rrichards@trynorthpoint.com | www.financewithteamrichards.com 204 Turnpike Rd, Westborough, MA 01581 Licensed in MA, CT, FL, NC, NH, PA, RI Follow us on Instagram @financewithteamrichards @the.longgamepodcast