Chicago, Illinois
Donald T. Spann
Serial entrepreneur, investor, lifelong Chicagoan at heart.
Twenty-time Founder. 4 exits and counting. I build companies that answer the phone, show up on time and do the unglamorous work well — and I back founders doing the same.
Currently building
Companies I run today
Call Canna
2022Founder
A contact center built for plant-touching cannabis businesses — US-based and offshore teams with deep expertise in compliance, pharma and customer support.
Visit site →LifeTech Staffing
2024Co-Founder, Head of Sales
A boutique staffing firm placing life sciences and AI talent, from SMBs to the Fortune 500, with a decade-plus of recruiting behind it.
Visit site →Switchboard Consultants
2021Founder
Call center implementation services.
Visit site →Hybrid Call Center Class
2026Creator
A course on how to build a Voice AI and Human powered contact center.
Visit site →Stealth Venture
2026Founder
A stealth call center in the healthcare space.
In stealthFounded & built
Companies I've exited
Vicky Virtual Receptionists
Live, human receptionists answering calls for small businesses across the US.
Companion Maids
On-demand residential cleaning, built and scaled in the Chicago market.
Rentobo
Software and services for independent landlords and property managers.
Flashy Photobooth
An early venture in on-demand consumer services.
Investing
Where I put capital
Investor & Advisor
FigTree Delivery Services
Last-mile delivery infrastructure for regional retailers.
Angel
Early-stage service businesses
Checks and hands-on operating help for founders building unglamorous, cash-flowing service companies.
Advisor
Operator-led rollups
Backing operators acquiring and modernizing home and business services.
Board & community
Where I give back
Board Member
Poder
A Chicago non-profit that helps immigrant adults build English fluency, digital skills and career pathways to economic mobility. I serve on the board, supporting the organization's growth, workforce partnerships and long-term strategy.
Youth Mentor
NFTE
Mentoring young people through NFTE's entrepreneurship programs — helping students turn an idea into a real business plan, and showing them that a founder's life is available to them too.
Legacy Mentor
Legacy Leaders
Serving as a Legacy Mentor — walking alongside the next generation of leaders and helping them build the habits, relationships and purpose that outlast any single venture.