On The Ground

Raissa Allaire on Growing a Nonprofit from Cat Rescue to Feline Welfare, Board Trust, and Agentic AI in FundraisingRaissa Allaire, CEO of Treehouse Humane Society, joins host James Misner to share how the Chicago nonprofit grew from a cat-adoption organization into a broader feline-welfare provider. That growth includes a low-cost veterinary wellness center and community-focused programs. She offers practical lessons on nonprofit leadership, board trust, and fundraising growth. She also explains how Treehouse uses agentic AI to extend donor outreach without replacing human relationships.This conversation is especially relevant for nonprofit executives, board members, fundraisers, and anyone curious about using AI responsibly in donor engagement. Raissa reflects on her path from museums and social services into animal welfare. She closes with a candid look at learning to pause and celebrate progress, and with the question that drives Treehouse’s vision: where do we get to a world where cats don’t need rescuing?In this episodeHow Treehouse Humane Society, founded in 1971, expanded from fostering and adopting cats to prevention, community programs, advocacy, and a veterinary wellness centerRaissa’s path from museums and social services into animal welfare, and the transferable skills in programming, operations, fundraising, finance, and board leadershipWhy comfort with ambiguity and quick learning from mistakes are core leadership skillsThe “no surprises” approach to building trust between a CEO and the boardWhy Raissa made no changes in her first three months in 2018 and spent that time on a listening tour that honored the organization’s historyHow the low-cost veterinary wellness center, opened in 2021, can serve up to 6,000 pets a year and provides about $100,000 in free or discounted servicesThe lesson in listening to concerns about AIHow Treehouse’s two AI fundraising agents, Carmen and Herb, reach donor portfolios the team lacks capacity to serve personally, with human escalation, guardrails, and opt-outs of about 0.7%How revenue grew from roughly $1.8 million to an average of about $7 million, supported by reserves and investments in major gifts, legacy giving, direct response, and fractional expertiseWhy events are an important strategy “within reason,” and why financial resilience and discipline matterUsing an executive coach and learning to pause and celebrate progressTreehouse’s future priorities: expanding access to veterinary care, targeted advocacy, and connecting pet welfare with housing, food, and social servicesTimestamps00:00 – Treehouse’s evolution from rescue to prevention 02:03 – From museums and social services to animal welfare 04:11 – Leading through ambiguity and building board trust 07:46 – Why Raissa began with a listening tour 10:42 – Opening a low-cost veterinary wellness center 12:36 – The lesson in listening to AI concerns 15:16 – How Carmen and Herb extend donor outreach 18:39 – Growing revenue from $1.8 million to $7 million 21:24 – Celebrating progress and using an executive coach 24:32 – Treehouse’s vision: access, advocacy, and connected services 27:19 – How to find Treehouse and visit its cat cafeResources & Links:The Kipos Group WebsiteSchedule a Discovery Call with JamesConnect with James Misner on LinkedInConnect with Raissa and Treehouse:Treehouse Humane Society Official WebsiteConnect with Raissa on LinkedIn

Karen Houghton on Building Nonprofit Financial Resilience, Smarter Reserves, and Stock Gift ReadinessKaren Houghton, founder of Infinite Giving, joins host James Misner to explain how nonprofits can build financial resilience and better steward their funds. Drawing on her experience in the nonprofit, technology, and venture-capital worlds, she breaks down reserve targets, safer cash management, endowments, and why nonprofits need the infrastructure to accept stock gifts and other assets.This conversation is especially relevant for nonprofit leaders, finance staff, board members, and fundraisers. Karen reflects on her path from founding a nonprofit in Rwanda and East Africa to building a company that serves more than 500 nonprofits across 43 states, and she closes with a lesson on failure: learn from setbacks without attaching shame to them.In this episodeKaren’s path from founding a nonprofit working in Rwanda and East Africa to technology, venture capital, and Infinite GivingHow Infinite Giving supports more than 500 nonprofits across 43 states with financial infrastructure and stewardshipWhy six to twelve months of reserves is a common healthy target, and why the right level depends on each organizationThe difference between liquid, lower-risk cash management and longer-term investingWhy endowments need an investment strategy instead of sitting in checking or savings accountsAlternatives to low-yield bank accounts, including FDIC sweep coverage, money markets, and Treasury securitiesHow brokerage accounts and stock-gift capability connect to donor access, tax efficiency, and less friction in givingWhy accepting stock and legacy gifts helps small and midsized nonprofits reach assets beyond credit- and debit-card donationsKaren’s perspective on failure: learn, keep trying, and avoid shameTimestamps 00:00 – From nonprofit founder to building Infinite Giving 04:12 – Serving 500-plus nonprofits across 43 states 06:09 – Why reserves create continuity for mission-driven work 08:27 – Spotting reserve gaps and idle cash 11:33 – Cash management, FDIC coverage, and lower-risk options 15:39 – Why endowments need a long-term investment plan 18:12 – How much should a nonprofit keep in reserve? 20:04 – Brokerage accounts, stock gifts, and donor opportunity 28:59 – Making brokerage accounts and stock donations easier 31:36 – Learning from failure without shame 33:38 – Karen’s books and how to connectResources & Links:The Kipos Group WebsiteSchedule a Discovery Call with JamesConnect with James Misner on LinkedInConnect with Karen:Infinite Giving Official WebsiteConnect with Karen on LinkedIn

Rae Martin on Building St. John Center’s Homeless Services Continuum and Doubling the BudgetRae Martin of St. John Center in Louisville shares how the organization serves people experiencing homelessness through a continuum of care from day shelter and outreach to permanent supportive housing. She also explains how careful preparation and a mix of public, philanthropic, and housing-finance support helped make Sheehan Landing possible.This conversation is especially relevant for people working in homelessness services, nonprofit leadership, and fundraising. Rae reflects on her path from educator to organizational leader, the funding strategy behind St. John Center’s growth, and lessons learned from efforts that didn’t go as planned.In this episodeSt. John Center’s day shelter, outreach program, and permanent supportive housingSheehan Landing and housing options for people with complex support needsThe scale of homelessness and demand for services in LouisvilleRae’s leadership journey, from Youth Build to St. John CenterHow advance planning helped the organization act when funding opportunities aroseHow public funding, housing tax credits, and a development partnership helped finance Sheehan LandingThe role of HUD grants, rental assistance, and housing vouchers in supporting operationsGrowing operating support through public funding, foundations, and other partnershipsThe challenges of Medicaid billing and generating revenue as an affordable housing providerHow volunteers, donors, and community partners support St. John Center’s workTimestamps00:00 – Rae Martin and St. John Center’s mission00:27 – The organization’s programs and services01:30 – Outreach and permanent supportive housing03:48 – The scale of homelessness in Louisville05:52 – Rae’s leadership journey07:59 – Why housing stability matters09:52 – Finding her way to St. John Center13:13 – The organization’s growth and new housing facility14:58 – Preparing for funding opportunities16:43 – Bringing funding sources together for Sheehan Landing18:09 – Funding supportive services and housing operations21:00 – Growing the operating budget24:03 – Medicaid billing and long-term sustainability25:16 – Lessons from strategies that didn’t work29:29 – How to connect with St. John Center30:19 – Volunteers, community support, and upcoming eventsResources & Links:The Kipos Group WebsiteSchedule a Discovery Call with JamesConnect with James Misner on LinkedinConnect with Rae:St. Jhonn Center Official WebsiteConnect with Rae on Linkedin

Why fractional support can help nonprofits do more with lessNicole Kirkorian Elmes, CEO of MissionWell, joins James Misner to talk about her path from Disney and DoorDash into nonprofit support work, and why fractional services can be a smart fit for organizations that need senior-level help without adding full-time headcount. They also dig into what nonprofits actually need to run well, from finance and HR to board support, and why the sector is often more resilient and resourceful than people assume.In this episode:How her career at Disney and DoorDash shaped a people-first leadership style focused on making life easier for othersWhy she moved into nonprofit and faith-based work after finding herself drawn to boards, church service, and community leadershipWhat “fractional” means in practice: flexible support that can scale up or down based on organizational needHow MissionWell can function as a finance department, HR partner, or board support resourceWhy a fractional model can cost less than hiring a full in-house team, while also reducing management burdenThe kinds of work MissionWell handles, from bookkeeping and controller-level finance to CHRO work and organizational designHow board services help clarify oversight, recruiting, and the division between staff and board responsibilitiesWhat Nicole is seeing across the nonprofit sector, including growth in niche organizations and strong appetite from donors and supportersWhy strong systems, clear roles, and good HR practices matter if a nonprofit wants to “run like a business” in the right waysHow volunteer leadership is different from employee management, and why finding the “low lift” is key to avoiding burnoutTimestamps00:00 – Meet Nicole Elmes and her journey to MissionWell01:16 – From Disney and DoorDash to nonprofit leadership03:06 – How church and board service led her to MissionWell04:50 – Disney’s Tangled and a successful movie launch06:45 – Understanding fractional support for nonprofits09:39 – MissionWell’s finance, HR, and board services11:27 – The growth of specialized nonprofit organizations14:45 – Cost benefits of fractional vs. in-house support16:36 – Technology, digitization, and strategic efficiency18:05 – The challenges of wearing multiple hats20:25 – Why nonprofit leaders hesitate to outsource21:59 – Nicole’s biggest surprises in the nonprofit sector25:11 – Running nonprofits with a business mindset27:49 – Rethinking volunteer leadership and preventing burnout30:46 – Challenges and lessons from scaling MissionWell32:15 – Connecting with Nicole and MissionWellResources & Links:The Kipos Group WebsiteSchedule a Discovery Call with JamesConnect with James Misner on LinkedinConnect with Nicole:Missionwell Official WebsiteConnect with Nicole on Linkedin

Daniel Drewski on Character, Collaboration, and Fundraising That LastsJames Misner talks with Daniel Drewski, president and CEO of International Leadership Institute, about developing leaders across more than 100 nations and 70 languages. They explore why character is foundational to effective leadership, how to collaborate across cultures, and what sustainable fundraising looks like for nonprofits and ministries.Daniel shares lessons from his career in politics, hospitality, education, and global ministry including how to build systems that can outlast any one leader.Key topicsDaniel’s journey to leading International Leadership Institute as its first successorThe importance of local leaders and character developmentThe “tyranny of the urgent” and the apartment-fire analogyFour keys to collaboration: shared goals, success measures, support, and communicationNavigating cultural differences with graceHow scarcity thinking affects partnershipsBuilding sustainable fundraising systems and prioritizing relationshipsLessons from an event with competing goalsDaniel’s vision for developing leaders and closing leadership gapsTimestamps00:00 – Introducing Daniel Drewski and global leadership00:31 – Daniel’s journey at International Leadership Institute01:49 – Local leadership and community transformation03:24 – Character development in leadership04:14 – The apartment-fire analogy and leadership urgency06:36 – The tyranny of the urgent and succession08:28 – Cultural differences and good character11:52 – Shared goals, success measures, and communication13:20 – Scarcity thinking and its impact on partnerships14:14 – Turning concerns into action18:28 – Fundraising lessons and sustainable systems20:36 – Major gifts, grassroots support, and relationships24:45 – Fundraising failures and lessons learned28:06 – The importance of clear fundraising goals29:48 – Stewardship and scarcity31:17 – Daniel’s five-year vision for leadership33:45 – Preparing leaders for growth34:56 – Connecting with Daniel and International Leadership InstituteResources & Links:The Kipos Group WebsiteSchedule a Discovery Call with JamesConnect with James Misner on LinkedinConnect with Daniel:International Leadership Institute Official WebsiteConnect with Daniel on Linkedin