From T-Shirts to Impact: How I Built the Stupid Cancer Store

In 2012, we sold our first white Gildan 5000 t-shirt for $20. There was no inventory system, no marketing funnel, and no real supply chain. But that one shirt — with “Stupid Cancer” boldly printed across the front — sparked something bigger than I ever imagined.

What started as a side project to raise a little awareness and a few dollars for a cause close to my heart quickly became a fully operational lifestyle brand. Along the way, we outgrew systems, learned from stockroom mistakes, and navigated the unique balance of nonprofit values and ecommerce hustle. This is the story of how the Stupid Cancer store came to life.

Why We Needed a Store in the First Place

The Stupid Cancer community is bold, passionate, and proud. As a nonprofit focused on supporting young adults affected by cancer, our messaging was never subtle — and neither was our brand. People didn’t just want to donate; they wanted to wear their support. They wanted to make a statement.

At the time, we were using CafePress — a print-on-demand platform that allowed us to offer some designs, but we had limited control over quality, fulfillment, and, most importantly, profit margins. It was time to bring ecommerce in-house.

But as a nonprofit, we had to be smart. Donor dollars couldn't fund the merch line. So we launched the store with one low-risk product: a white tee, printed in bulk, paid for out-of-pocket. We built everything else from the ground up.

Building the Store, One App at a Time

As Chief Operating Officer, I wore a lot of hats — and one of them was ecommerce manager. I designed the early store infrastructure around automation, integration, and scalability. Our first major platform was Volusion, but I quickly realized we needed more customization and better reporting tools. That led us to Bigcommerce, a platform that offered the flexibility I needed to tinker under the hood.

Apps became my team.

• Slack gave me a dashboard to watch customer activity, Zendesk tickets, and incoming orders — all from my phone.

• Zapier and Kevy were the glue, connecting platforms like PayPal, Trello, and Mailchimp without writing a single line of code.

• Evernote became my product spec vault.

• Inventory Planner helped me make smarter purchasing decisions and understand product velocity.

• Zendesk allowed us to manage omnichannel customer service across email, Facebook, and Twitter, without letting anything fall through the cracks.

Without these tools, there’s no way we could’ve scaled the store — especially with a lean team and no dedicated ecommerce department.

From Tiny TriBeCa Office to a 3PL

Initially, I fulfilled every order by hand — literally packing and shipping shirts out of our Lower Manhattan office. Eventually, the growth caught up with us. We ran out of space and time.

The next milestone was transitioning to a third-party fulfillment partner (3PL). After attending eTail West and getting a few rejections for being too “small,” I found a partner in Karol Fulfillment in Pennsylvania. They understood our needs, automated our inventory management, and helped us scale up production without sacrificing flexibility.

The move allowed us to expand our product line — more colors, more sizes, more types of apparel — without worrying about how we’d store or ship it. It also enabled us to take advantage of bulk pricing, lowering production costs and improving margins while still keeping prices accessible for our community.

Profit vs. Purpose: Walking the Line

We were never in it for the profit — but that doesn’t mean the store didn’t have to operate like a real business.

Yes, the store helped fund programs and overhead. But for me, it was equally valuable as a visibility engine. Every person wearing a Stupid Cancer shirt was a walking billboard for the movement.

That’s why we sometimes sold items at a loss or ran flash sales and free shipping weekends. We launched “grab bags” full of retired designs and promo items, just to surprise customers and keep the momentum going. It wasn’t just ecommerce — it was community-building through merchandise.

I was also keenly aware of our audience. Many of our customers were in treatment or financially strained. So while I aimed for a 50% gross margin, I never let the numbers override our mission. We priced with empathy.

Lessons from the (Virtual) Frontlines

Over the years, I’ve made plenty of mistakes — ordered too many shirts, misjudged which designs would resonate, neglected to use minimum inventory alerts — but each mistake taught me how to run a smarter, leaner operation.

Some of my key takeaways:

• Automate early, and often. Time is your most valuable asset, especially when you’re wearing multiple hats.

• Don’t over-order. Stale inventory isn't just a cash drain — it becomes a storage problem if you're using a 3PL.

• Use pre-orders to test demand. One of our best sellers was a holiday sweater we launched via a 99Designs contest and pre-sold through email and social media.

• Design matters, but community matters more. Our best customers didn’t just like the design — they loved what it stood for.

The Results

Since 2012, the Stupid Cancer Store has fulfilled thousands of orders and created millions of impressions for the Stupid Cancer brand. It has funded programs, sparked conversations, and connected survivors in ways we never could have predicted.

But more than anything, it proved something I believe deeply: Nonprofits can — and should — build revenue models that are mission-aligned, community-centered, and operationally strong.

Ecommerce wasn’t just an income stream for us — it was a catalyst for awareness, engagement, and loyalty.

Final Thoughts

If you’re a nonprofit thinking about starting a store, do it with intention. Don’t aim to just “sell stuff.” Build something that deepens your community’s connection to your mission. Use tools that scale with you. Track what matters. And above all, remember that every shirt, hat, or hoodie is an opportunity for someone to say, “Hey, me too.”

Because when it comes to impact, that’s where the magic starts.

Nonprofit Degree vs. On-the-Job Experience: What Prepares You Best?

If you’ve ever considered a career in the nonprofit sector—or if you're already deep in it—you’ve probably wrestled with this question:

Should I get a degree in nonprofit management, or just learn by doing?

I’ve walked the on-the-job path. And while I now see the value in academic credentials, I also know that no textbook fully prepares you for what happens in the trenches.

The Power of On-the-Job Experience

When I helped build Stupid Cancer, we were a scrappy, mission-first team doing everything from fundraising and programming to eCommerce and digital engagement. There wasn’t a manual for launching awareness tours across the country or building one of the first apps for cancer patients (Instapeer). There was just the work—and the urgency to get it done for the people we served.

Later, as Board Chair of YNPN-NYC, I saw a different side of nonprofit leadership—governance, strategy, and the challenge of sustaining an all-volunteer board while trying to modernize systems, upgrade member engagement, and remain relevant in a city full of worthy causes.

That experience taught me more about nonprofit dynamics than any classroom could. I learned:

• How to motivate teams without money

• How to stretch resources across time zones and time crunches

• And how to fail fast, pivot, and still show up the next day with purpose

These were my "degrees" in real time—earned through community-building, burnout, and breakthroughs.

The Case for a Degree (and a Strong One at That)

That said, I’ve come to appreciate the structure, theory, and credentialing that a graduate program can offer. One that stands out is the Master of Science in Nonprofit Administration (MSNPA) at Louisiana State University Shreveport (LSUS).

This fully online program is designed for working professionals and taught by faculty with hands-on nonprofit experience. You can choose from tracks in:

• Nonprofit Administration

• Nonprofit Development

• Disaster Preparedness

It’s one of only a handful of programs accredited by the Nonprofit Academic Centers Council (NACC)—a mark of academic and sector credibility. And it can be completed in as little as 12 months.

If I’d had this kind of structured training earlier in my journey, I might have avoided a few growing pains—or at least had the language to describe what I was already doing instinctively.

So, Which One “Wins?”

The best nonprofit leaders I know find a balance. They blend practical, on-the-ground knowledge with the frameworks and theories that help them scale their efforts responsibly.

If you’re just starting out, get your hands dirty. Work or volunteer for an organization like the one you want to lead someday. But if you’re mid-career or eyeing executive leadership, a program like LSUS’s MSNPA can equip you with tools, confidence, and credentials to take the next step.

Legacy Projects and Letting Go

I’ve spent the better part of my career building things—some big, some small, some messy, some magical. A few have made headlines. Others were just a shared Google Doc, a Slack channel, or a late-night whiteboard brainstorm that turned into something real.

But here’s the truth: not everything I’ve built still exists.
And that’s not a bad thing.

The Branded Car and the Open Road

From 2012 to 2016, I helped lead the Stupid Cancer Road Trip—an annual campaign where we drove across the country in a car wrapped bumper-to-bumper in our logo and mission. This wasn’t a quiet awareness effort. It was bold, loud, and impossible to miss.

We rolled through major metros and small towns—Washington, Chicago, Portland, Billings, Anchorage, Vegas—meeting young adults affected by cancer in hospital lobbies, dive bars, parking lots, and everywhere in between.

Those trips were never meant to last forever. They were meant to spark connection and show people that they weren’t alone.
And they did.

People still ask me, “What happened to the road trips?”
And I tell them: They did exactly what they needed to do.

The App That Came Before Its Time

Another one of those projects was Instapeer—the first-ever mobile app designed to connect cancer patients and survivors based on shared variables in their experience: diagnosis, age, treatment type, gender, identity, and more.

At the time, nothing like it existed. We weren’t just building an app; we were building digital empathy. A way for someone going through hell to find someone else who'd been there and made it out the other side. Peer support, but modern. Mobile. Human.

Instapeer was ahead of its time—built on heart and limited resources. We learned fast, failed fast, pivoted hard, and made thousands of meaningful matches. And while it’s no longer live today, I still hear from people who say it helped them feel seen when they needed it most.

The app didn’t need to last forever to matter.
It did what it came here to do.

Impact Doesn’t Always Mean Endurance

I’ve built internal systems and workflows, too—some with duct tape and prayer, others with APIs and strategy. Many are gone. And that’s fine.

Legacy isn’t always about maintenance.
It’s about meaning.

Did the thing serve the moment?
Did it change someone’s experience?
Did it make the work better, easier, or more human?

If yes, that’s success. Even if the servers get shut down or the van gets parked for good.

What I Choose to Keep

I’ve let go of logos, domains, passwords, platforms, and programs. But I’ve kept the lessons, the momentum, the people, and the purpose.

Letting go isn’t giving up.
It’s giving space.

And when I think back—whether to a wrapped road trip car or an app that let strangers become lifelines—I don’t feel loss. I feel gratitude.

The wheels stopped turning. The app stopped loading.
But the impact? Still moving.

To the Class of 2025 — and to My 2010 Self

A letter to the scrappy, unsure, big-hearted version of me — and maybe you too.

In 2010, I was fresh out of college, trying to figure out how to turn passion into a paycheck. I didn’t have a roadmap — just curiosity, a work ethic, and a relentless belief that I could build something meaningful.

Looking back now, with a few companies under my belt, nonprofit chapters written, and lessons learned the hard way — I wanted to write a letter to that younger version of myself. The version who was unsure but driven. The one who had no idea what was coming but showed up anyway.

This letter is for him — and for every recent grad standing at the start line of their own story.

Dear Kenny (2010 Version),

You’re standing at the edge of something. You’ve got the degree, a few wild ideas, and a ton of heart. You’re not totally sure what’s next — only that you want to do something that matters.

I remember. I was you.

If I could go back and sit across from you — hoodie, iced coffee, big dreams, probably building a website on a secondhand laptop — here’s what I’d tell you.

1. Start scrappy, but think scale.

Don’t wait for perfect. Ship the thing. Try the idea. Build the deck. But while you’re duct-taping it together, start thinking about how this thing could run without you. That’s the difference between hustle and growth.

2. Your empathy is your edge.

You’re going to walk into boardrooms and pitches and meetings where people care more about spreadsheets than stories. Don’t shrink your empathy to fit in. It’s what will make you a great leader.

3. Making money doesn’t mean selling out.

You can do good and do well. Nonprofits, startups, agencies — all of them need fuel to run. Revenue is not a betrayal of your values. It’s how you keep the mission alive.

4. Say yes to the road trips.

Take the detour. Do the tour. Pack the car and drive across the country for a cause you believe in. Some of the best chapters of your life won’t show up on a resume, but they’ll shape who you become.

5. Job titles won’t define you.

You’ll be a director before you're 30. A CEO not long after. But the real wins? They’ll come when you stop chasing roles and start building systems, movements, and teams that outlast you.

6. You will be underestimated.

Because you’re young. Because you’re not the loudest voice. Because you use Slack and care about mental health. Good. Let them underestimate you. You’ll let your results do the talking.

7. Guard your energy like it’s capital.

You’ll want to do it all — and you might. But if you burn out, none of it lasts. Rest. Delegate. Say no to things that don’t light you up or lift others.

8. Every bit of it matters.

The 2 a.m. website rebuild. The failed fundraiser. The awkward pitch that gets ignored. All of it is building muscle. And one day, you’ll look back and realize: that mess became momentum.

9. You’ll lead in a way that doesn’t look like leadership.

You won’t be the loudest. You’ll care more about culture than control. You’ll prefer questions over speeches. That’s okay. That’s how things change.

10. Back up your files.

Seriously.

To anyone reading this on the edge of your career — maybe you're not sure if you're ready. Let me say this clearly:

You are.

And the road ahead? It’s going to surprise you in the best ways.

Keep showing up. Keep learning. Keep building.

We’re just getting started.

— Kenny Kane
CEO, Builder, Former Road Tripper, Forever Grad

How I Use ChatGPT to Work Faster, Smarter, and Keep My Head on Straight

Like most people juggling a few too many things, I’m always looking for ways to get more done without losing my mind—or my voice. That’s where ChatGPT comes in.

What started as curiosity has turned into a full-blown part of my workflow. It’s like having a really fast, always-available collaborator who never gets tired of drafts, rewrites, or random questions at odd hours. Here’s how I use it in real life:

1. Writing Stuff (Without Staring at a Blank Screen)

Whether it’s an email, blog post, board update, or internal doc, I usually start with a few bullet points or a messy brain dump and let ChatGPT help shape it into something that actually makes sense. It’s saved me hours—probably days—over time.

2. Keeping My Voice Consistent (Even When I’m Rushed)

Running both a business and a nonprofit means I’m talking to members, donors, staff, and investors—sometimes all in the same day. ChatGPT helps me keep the tone and message consistent without sounding robotic or like I copied and pasted the same thing to everyone.

3. Brainstorming When I’m Stuck

Sometimes I just need to shake things loose—whether I’m naming a campaign, outlining a project, or trying to make a point more clearly. I’ll toss a few ideas into ChatGPT and see what comes back. A lot of it I don’t use, but almost always, it gets me to a better place faster.

4. Fixing the Boring but Important Stuff

I’ve used ChatGPT to draft or clean up lease language, policy updates, and other operational docs. It’s not flashy, but it’s incredibly helpful for getting something 90% of the way there so I’m not starting from scratch.

5. Helping Me Write a Book (Without Going Crazy)

I’m working on a book called The Tech-Forward Non-Profit, and ChatGPT has been huge for helping me organize my thoughts, draft chapters, and figure out how to say things in plain English. It’s like having a writing buddy who never needs coffee breaks.

Bottom line: ChatGPT doesn’t do the thinking for me—but it helps me think faster, communicate better, and focus on what really matters. It’s not magic, but it’s pretty close.

What Tech-Forward Nonprofits Get Right — and Why Most Are Still Behind

The nonprofit sector has always been resourceful, scrappy, and mission-driven. But in 2025, that’s not enough.

Tech-forward nonprofits — the ones leading the charge in fundraising, engagement, and operational efficiency — aren't just using better tools. They’re thinking differently. They understand that technology isn’t a luxury or a line item — it’s infrastructure. It’s culture. It’s survival.

So what exactly are they doing right? And why do so many others struggle to catch up?

1. They treat operations as a growth engine, not overhead.

Most nonprofits still treat operations and tech as necessary evils — boxes to check, budgets to slash. Tech-forward orgs flip the script. They invest in systems, automations, and analytics because they know it pays off in time, transparency, and trust.

💡 If you're still tracking donors in spreadsheets or manually replying to every volunteer inquiry, you're spending energy where automation could scale your impact.

2. They build tech stacks that serve people — not the other way around.

The best nonprofits don’t just chase flashy tools. They select platforms that make life easier for staff, volunteers, and supporters. They understand integration, user experience, and most importantly — that the tech exists to serve the mission, not the other way around.

Whether it’s using Zapier to sync Mailchimp and Salesforce, or Slack to replace 100 email threads, they streamline to empower.

3. They act like media companies.

Modern donors aren’t moved by glossy annual reports. They want real stories, real-time updates, and authentic content. Tech-forward nonprofits use blogs, video, email, and social with the cadence and creativity of a startup — not a government agency.

They think in campaigns, not just appeals. They test, they track, and they iterate. That’s how they stay relevant in an attention economy.

4. They prioritize data literacy across the org.

It’s not enough for “the tech person” to know how the CRM works. The whole team — from development to programs — needs to understand how to collect, interpret, and act on data.

The smartest orgs normalize dashboards, KPIs, and performance reviews not to add pressure, but to create clarity. When data is democratized, so is decision-making.

5. They embrace a culture of experimentation.

Tech-forward nonprofits understand that done is better than perfect. They run pilots, try new platforms, launch MVPs of programs. Failure isn’t feared — it’s a feedback loop.

The rest? They’re stuck in endless committee meetings, legacy systems, and outdated playbooks. And by the time they finally act, the opportunity’s moved on.

Why Most Are Still Behind

• Fear of change. Culture eats strategy for breakfast — and nonprofits with deep traditions or risk-averse boards struggle to move fast.

• Burnout. Overworked teams don’t have the bandwidth to learn new tools, let alone optimize them.

• Budget bias. Many funders still don’t prioritize infrastructure — and nonprofits internalize that as gospel.

• “Nonprofit exceptionalism.” The belief that what works in the for-profit world can’t apply to mission-driven work is a limiting myth.

Final Thoughts

Technology isn’t the silver bullet — but it’s the lever. When done right, it unlocks time, transparency, and transformation. The nonprofits leading the future are already acting like modern organizations — fast, data-informed, human-centered.

The good news? It's never been easier to get started. You don’t need to overhaul everything overnight. But you do need to start thinking like a tech-forward nonprofit, not just a well-intentioned one.

Let’s build missions that scale.

The Tools I Actually Use: My Cloud Stack for Running a Modern Business

There’s no shortage of SaaS tools promising to make your business faster, smarter, or more automated. I’ve tested dozens. Some stick. Some don’t. This is my current cloud stack—what I use every day to run operations, stay organized, and keep our teams productive and aligned. It’s not theoretical. It’s battle-tested.

Communication & Collaboration

• Slack: The central nervous system of the team. Replaces most internal emails and keeps decision-making transparent.

• Asana: Where projects go to live (and ideally, to die completed). Simple, visual task management that scales from personal to team-wide execution.

• Intermedia Elevate: Business phone, voicemail, conferencing—still necessary for some of the old-school workflows.

Sales, Marketing & Automation

• LeadSimple: Our lead tracking and CRM layer. Clean and focused on sales workflows without being bloated.

• Mailchimp: Email marketing workhorse. Solid for newsletters, announcements, and drip campaigns.

• SEMrush: For keeping tabs on keywords, SEO performance, and competitive search data.

• Fathom Analytics: A privacy-first alternative to Google Analytics. Fast insights, no creepy tracking.

• Zapier: The duct tape of automation. It connects nearly everything here, saving hours on repetitive tasks.

• ChatGPT: A new daily companion—for drafting emails, writing code, summarizing documents, and brainstorming ideas. Not replacing people, but multiplying output.

Web Presence

• WP Engine: Hosting our legacy WordPress sites. Reliable, fast, and easy to manage at scale.

• Squarespace: Used for past microsites or when we need quick visual polish without a dev team.

• Framer: Our new go-to for fast, beautiful, responsive sites. I built a live site in about an hour—no code needed.

Documents & Content Creation

• DocuSign and HelloSign: We still use both depending on partner preferences, though we’re likely to consolidate soon.

• Canva: Where we create everything from pitch decks to social assets. Design for non-designers and fast-moving teams.

Tools I Tried and Ditched

• PandaDoc: Slick interface but redundant once we committed to HelloSign and DocuSign.

• Blaze.ai: A promising AI content tool, but it didn’t save time in our real-world use cases.

Lessons Learned

• Don’t chase shiny tools. If it doesn’t save time, increase revenue, or reduce complexity, it’s out.

• Integrations matter more than features. Zapier is often the glue that turns “nice to have” into “must-have.”

• AI tools are like interns—great for drafts and research, but still need review.

• When in doubt, simplify. More tools mean more training, more maintenance, and more chances for things to break.

What’s Next
I’m always testing new tools, but they have to prove their ROI quickly. The future stack will likely include more AI-native platforms, lighter CRMs, and fewer tools doing more.

How I Earned My MBA Without Pressing Pause on Life

I’ve always believed that hustle, curiosity, and a strong sense of purpose can take you far. My communications degree from Farmingdale State College—and a can-do attitude—launched my career across startups, national nonprofits, and now a multi-market real estate company. But for years, I had an MBA in the back of my mind.

Not because I needed more credentials—but because I wanted a formal way to strengthen the areas I had taught myself on the fly: finance, strategic planning, marketing analytics, and operations at scale.

After relocating to Austin, I looked at programs like UT and Baylor. Great schools, no doubt—but the time and financial commitment were tough to justify. I couldn’t (and wouldn’t) step away from my work and family for weekend residencies or $70K price tags.

Then one day in August 2023, I got a push notification from r/MBA—a subreddit I’ve followed for years. It mentioned Louisiana State University Shreveport’s online MBA program. Fully accredited, asynchronous, and priced under $13,000 total. I had one thought:

What’s the catch?

Turns out, there wasn’t one.

Applying to LSUS

I submitted my application just days before the fall term started. It was refreshingly simple: a short form, emailed transcripts, and a quick turnaround. Within 24 hours, I was accepted. I was officially enrolled in the Accelerated Online MBA – General Business program, and ready to see what it was all about.

What followed was a year-long sprint—10 courses completed in just over 13 months, all while leading my company, supporting my family, and still finding the occasional moment to breathe.

What I Learned (And Why It Mattered)

The LSUS structure runs in seven-week terms with a one-week break between blocks. It’s fast-paced, but manageable. Here's a quick look at the courses I took and what stood out:

🔹 MBA 705: Organizational Strategy & Policies

A strong opener. Dr. Michael Meeks delivered concise, pre-recorded lectures that made expectations crystal clear. Weekly group projects over Zoom added collaboration without chaos.

🔹 MBA 758: Casino & Resort Management

Yes, it’s a real class—and surprisingly strategic. A creative lens on market analysis and customer experience.

🔹 MBA 761: Entrepreneurship, Innovation & Creativity

Given my background, this one hit home. It helped me put language and frameworks around instincts I’ve followed for years.

🔹 MBA 703 & 704: MIS + Organizational Behavior

Two solid courses that helped me reframe how I manage systems and teams—particularly helpful in a remote or distributed work environment.

🔹 MBA 700 & 706: Accounting + Marketing Strategy

These were highly practical. Budgeting, positioning, targeting—it all shows up in my daily leadership work.

🔹 MBA 702: Financial Management

The only class I didn’t get an A in—and arguably the one that taught me the most.

🔹 MBA 742: Project Management

Straightforward, structured, and a great reinforcement of the way I run initiatives across markets.

🔹 MBA 701: Economic Analysis

A broad, data-driven wrap-up course that tied everything together.

Why It Was the Right Fit

LSUS wasn’t about prestige. It was about progress. The program respected my time, challenged my thinking, and gave me tools I could apply the same day. I didn’t need to hit pause on my company—or my life—to earn this degree. That flexibility, paired with a cost that didn’t require donor appeals or board votes, made it the right move.

I graduated in October 2023 with a 3.80 GPA—no capstone theatrics, just consistent effort and practical learning that stacked up week by week.

Final Thoughts for Fellow Professionals

If you’ve been sitting on the fence about going back to school—or wondering if an MBA is even worth it anymore—here’s what I’ll say:

You don’t need an MBA to be successful.
But if you want one to grow, to fill the gaps, to level up on your own terms—LSUS made that possible for me.

It wasn’t flashy.
It wasn’t expensive.
And it worked.

Questions about the program? Curious if it’s right for your path? I’m always happy to connect with others considering the same leap.

From Automation to Augmentation: How Generative AI is Changing Nonprofit Leadership

Ten years ago, I was using Zapier to duct-tape my nonprofit tech stack together. Stripe handled donations, Trello kept our roadmap alive, and Slack became our nervous system. Every app had a job. My job was to make them talk to each other—and not break anything in the process.

That DIY digital infrastructure helped me run lean, scale programs, and engage donors with minimal overhead. But it had limits.

Today, as a nonprofit executive in the age of generative AI, I’m no longer just automating tasks—I’m augmenting thinking.

And that’s a massive shift.

From Workflows to Thought Partners

Zapier and similar tools were built to move data between platforms. Generative AI, by contrast, helps move ideas forward. It doesn’t just connect systems; it complements human reasoning. It drafts, suggests, rewrites, brainstorms, summarizes, and learns from context.

When I first started out, writing donor emails meant opening a blank document and hoping inspiration struck. Today, I can feed AI a campaign goal, past donor copy, and a tone reference—and get a rough draft that sounds 80% like me. Then I make it 100%. That first draft doesn’t just save time—it gets me thinking faster.

The same applies to board updates, social posts, grant proposals, and even blog posts like this one. I’m not outsourcing creativity; I’m accelerating it.

AI Doesn’t Replace the Human—it Amplifies the Hustle

In the nonprofit world, we’re used to doing more with less. We’re also used to skepticism—of new platforms, shiny tools, and anything that promises magic. Generative AI isn’t magic. It’s leverage.

Here’s how I use it in my day-to-day:

• Drafting messages and letters to donors, funders, and partners

• Summarizing meetings or research into action items or decisions

• Rewriting internal docs to match tone, reduce jargon, or clarify expectations

• Prototyping ideas before bringing in designers or consultants

• Creating templates for fundraisers, board members, or volunteers

Compare that to 2014, when my biggest breakthrough was getting Mailchimp to automatically tag someone based on a Stripe donation. That’s not to diminish that work—it was necessary, and it worked. But AI brings a new layer: insight generation, not just workflow execution.

What Hasn’t Changed: The Need for Good Judgment

No matter how fast the tech evolves, the role of the nonprofit executive is still to lead with clarity, empathy, and purpose. AI won’t tell you how to navigate a community crisis. It won’t replace the board meeting where big strategy decisions get hashed out. And it won’t feel the weight of a parent calling you for help after a new diagnosis.

But what it can do is give you more space—mental, emotional, and operational—to show up where it matters most.

That’s the opportunity.

A Final Thought: Curiosity is the New Superpower

I never set out to be a “Chief Automation Officer.” I just wanted to build things that worked. Generative AI is just the next evolution of that mindset.

If you’re a nonprofit leader and you’re curious—even just a little—about how this tech might help you serve better, work faster, or think more clearly, lean in. Start small. Use it for that email you’ve been avoiding. Try summarizing that 10-page grant report.

You might be surprised at what you unlock.

And who knows? In another ten years, we may look back at today’s tools with the same fondness I have for Zapier and Slack. But right now, in this moment, we have a chance to redefine what it means to lead with both heart and horsepower.

Fifteen Years Later: From Intern to CEO, and Still Fighting Cancer Like Hell

Fifteen years ago, I stepped into the world of cancer advocacy as a college senior—just a kid trying to find purpose in the middle of uncertainty. My internship with the I’m Too Young For This! Cancer Foundation wasn’t just a way to finish school—it was the start of a lifelong commitment to a cause that would come to define much of my life’s work.

Back then, young adult cancer wasn’t even a conversation. There were no roadmaps, no big campaigns, and certainly no dedicated community for people in their teens, 20s, and 30s who were dealing with something as complex and life-altering as cancer. But I found myself surrounded by people who were not only living it—they were demanding change. That urgency, that defiance, lit a fire in me.

After graduation, I joined forces with a few brave souls and co-founded Stupid Cancer, building what would become one of the loudest, most irreverent, and impactful movements in young adult oncology. We didn’t have money or infrastructure. What we had was a bold name, a relentless work ethic, and a message that resonated: You are not alone.

I helped build the backend of the business. Websites. The store. Contributing to event logistics. The podcast. The merch. The fundraising platforms. If it touched a system, I had my fingerprints on it. I didn’t know then that I was helping build a startup disguised as a nonprofit. We went from zero to millions in donations. We traveled the country—yes, all 50 states—meeting patients, telling stories, and shaking loose the stigma that cancer was only for the old or the very young. We made survivorship mainstream. We made noise. We made it personal.

And then it got personal.

In 2005, just before all of this began, my dad was diagnosed with stage 2b testicular cancer. I was 18. He was 50. I watched my family walk the same tightrope so many of the people I would later meet were walking—fear, hope, confusion, gratitude. His diagnosis interrupted my prom, graduation, and the beginning of adulthood. But it also gave me my why. I didn’t realize it at the time, but everything I built from that point forward was for him—and for everyone who ever had to navigate that road without a map.

In 2016, I accepted the challenge of leading the Testicular Cancer Foundation as CEO, which brought me from New York City to Austin. Coming full circle—from a scared son to a seasoned advocate, from startup scrappy to scaling impact—has been nothing short of surreal. TCF is small but mighty. We raise awareness for a disease that is both highly treatable and tragically overlooked. We educate. We fund programs. We talk about balls—loudly and often. Because early detection saves lives, and silence helps no one.

This milestone—15 years—isn’t just a marker of time. It’s a reminder that advocacy isn’t a sprint. It’s not even a marathon. It’s a relay. And I’ve had the incredible privilege of running multiple legs of this race.

I’m not done yet. There’s more to build. More to disrupt. More to say. But today, I’m pausing to look back with gratitude—for the people I’ve met, the teams I’ve led, the lives we’ve impacted, and the purpose that keeps pulling me forward.

Thank you to everyone who’s been part of this ride.

Here’s to the next 15.

The Chief Automation Officer

I signed up for Zapier on March 5, 2014. I was Chief Operating Officer at Stupid Cancer at the time. Back then, I couldn't tell you what a cloud computing stack was, but I had one, and Zapier unlocked many doors and flipped on many light switches for me, professionally.

Three months after joining Zapier, Slack hit the market, and I was off to the races with automation. Suddenly every business data point was funneling into Slack as it quickly became the brain of Stupid Cancer. I have blogged in the past about Slack, so I will avoid doing that here. As a result, Slack dinged all day long at Stupid Cancer, and it still does in my various current roles.

When Wade Foster, Zapier CEO, posted this on LinkedIn, I felt seen:

Without realizing it, I have spent most of the past decade becoming a well-tuned Chief Automation Officer. It’s subtly been the hallmark of my career.

One of my favorite byproducts of automation is just how amazed people are at the very nature of it. There is little budget or margin of error for trying things out in the nonprofit world, especially with fundraising tools. Most fundraising platforms are awful and siphon much-needed funds out of charities to line their pockets. They would argue that they make it possible for nonprofits to be successful, and that's a debate I would love to have. I digress. People are amazed when you connect multiple apps, and data moves around 24/7.

With Zapier, we could suddenly do more than our out-of-the-box fundraising platform could do alone. I was not left wanting seven features and having to settle for four. I could have it all.

• I didn't need to export donors and import them into Mailchimp.

• I didn't need to watch my email for Stripe donations; I could get a Slack notification.

• I didn't need to create a to-do list task manually; Zapier took care of it.

My pivot to the private sector has created more meaningful automation opportunities in recent years. Now operating a membership-based company, my automation is focused on moving people through different states, such as lead, contact, active member, and former member. These states affect how we interact with you and your place in our cloud stack.

I wish I could say I spent a lot of time making flow charts and thinking about the end-to-end journey of my data. The reality, though, is most of my Zaps are born out of acute necessity and team inspiration. Perhaps one day, I’ll start keeping notes.

One consideration when running through the paces of creating automation is where Zapier fits alongside an app’s internal workflow system. Zoho Campaigns comes to mind in this example. I might use Zapier to get you from Facebook Leads to a Zoho Campaigns Mailing list with additional information. Still, I will let Zoho Campaigns read your contact record and qualify you for an email workflow. Keeping track of these relationships is essential so you don’t create loops or unforeseen automatic enrollment.

Automation can be daunting if you don’t know where to start. Services like Upwork have professionals for hire on a short-term basis to get you started. Once you start seeing what’s possible and connecting the dots between your workflows and cloud apps, you’ll get back those wasted hours doing things manually.

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Further reading:

• The emergence of the chief automation officer

• Chief Automation Officers Are The Answer … But What Is The Question?

My Smart Home

Years ago, sophisticated home automation seemed like an unattainable reality without the help of an electrician, networking expert, or a nerdy friend. The reality is that the market has a lot of options to smarten up your home. They range from the plug and play to flip-the-breaker installs.

A lot of these items come with different degrees of sticker shock. The configuration I am going to outline below was accumulated over many months, out of need and curiosity. When my wife and I bought a house earlier this year, it became clear that while not essential, these tweaks could significantly improve our quality of life. Onward!

Getting Started with Climate Control & Security

When we bought our home in May 2020, the first upgrade was swapping out the old Honeywell thermostat to a Google Nest Learning Thermostat. The home was unoccupied and temperatures in Central Texas were rising. I figured if I was going to be doing some form of pre-move manual labor, the thermostat was critical to cool off the house before I got there. Dropping the temps on moving day made the t-stat worth it.

As we settled into the new home, we realized that our bedroom ran hot at night. Our house is made of brick and gets sun on three sides. To solve this we put a Google Nest Temperature Sensor in the bedroom. During the day, I’ve got Nest prioritizing the hallway temperature, and overnight I’ve got the bedroom sensor controlling the system.

To round out our Nest install, I added two Google Nest Outdoor Cameras and a Nest Doorbell. I found this video really helpful when installing my cameras. With my Google Nest configuration set up to my liking, I moved on to the front door.

My three beautiful nieces live 500 feet away and often will come over to swim in our pool. I began to see a trend forming of us running through the house, dripping water, having to unlock or lock the front door. It became clear that, like the Nest Thermostat, a new August Wi-Fi Smart Lock would quickly pay for itself.

Keeping the Lawn Green

In Central Texas, your Bermuda grass can quickly go from green to white/yellow/brown if you’re not careful. Our new home came with a Hunter X-Core manual sprinkler controller. Between a broken dial and not knowing if the sprinklers were actually coming on at 5 am, I was ready for something a little nicer. Enter the Hunter Hydrawise WiFi-enabled controller. It’s got a great app to set up your programs and read reports on actual watering.

Network Coverage & IoT

As I began accumulating smart home devices, It was clear that my AT&T router wasn’t going to consistently support the diversity of devices both on the 5 GHz and 2.4 GHz. For those unfamiliar with the differences, Netgear sums it up well: 

The 2.4 GHz band provides coverage at a longer range but transmits data at slower speeds. The 5 GHz band provides less coverage but transmits data at faster speeds. The range is lower in the 5 GHz band because higher frequencies cannot penetrate solid objects, such as walls and floors.

As I began to flirt with the idea of upgrading my home network, I was quickly pointed in the direction of Unifi.

With a little bit of false confidence and a few hundred feet of cat6 cable, I began planning my wireless access point (WAP) plan. This was prior to Cardi B. ruining that acronym forever.

I decided to install two Ubiquiti Networks Unifi 802.11ac Dual-Radio PRO Access Point (UAP-AC-PRO-US) in the house. One in the hallway, visible from most of the large interior rooms in the house, and one on the back porch, ensuring full coverage over the pool and patio.

Once I had installed these two WAPs, I identified an opportunity to fill in the front part of the house by adding a Unifi Beacon HD Access Point.

In all, this setup has proven able to support all of my devices. One critical step is to turn off the internal WiFi in your cable modem as these are doing a much better job.

Lights. Cameras. Apple HomeKit.

Having done everything prior and paying the related credit card charges, I was ready to put a cherry on top of my smart home with some smart light switches. 

At my day job, I oversee commercial office space facilities, among other things. A couple of years ago, I was introduced to the Lutron Vive product line. It is an incredibly flexible solution in an environment with 100+ switches. The residential application, Lutron Caseta, is total overkill that is well worth the price of admission.

As with the rest of my smart home devices, I started with solving a problem before moving to non-essential purchases. First up was getting my Lutron Smart Start Kit to lay the foundation for what was to come.

With my Lutron environment established, I was free to begin expanding as I saw fit. My priorities were as follows:

• Turn exterior lights on at sunset; Turn off at sunrise

• Turn select interior lights on upon arriving at home

• Create scenes based on time of day or event

With this strategy in mind, I was able to use the Lutron app and Apple HomeKit to create some slick automation. When my wife or I arrive home, certain lights come on to welcome us. When we both leave, all of the lights shut off, with the exception of the exterior lights.

Along with this home occupancy logic, I have also programmed a few scenes in Apple HomeKit: 

• Party City: All common area lights up to 100%

• Relax: 7-9 pm lighting down to 30%

• Max Chill: Most lights off, one at 20%

• Leave Home/Goodnight: All lights off, except front exterior. (They run on Lutron sunrise/sunset schedule)

• Fans On: Sometimes the smoke detectors go off or the humidity level in the house rises, this quickly circulates air with the HVAC fan on and ceiling fans spinning.

Utilizing Apple HomeKit, I am able to have the majority of my products under one control panel. There are times when I will use a native app, such as the Lutron sunrise/sunset integration. There has also been one instance where I had to buy something to connect two devices that didn’t want to play nice together: Google Nest & Apple HomeKit. Of course, these two would not want to have their products integrate. Luckily, there is an aftermarket bridge that warms up this cold war and connects Nest to HomeKit. The Starling Home Hub plugs in to your network switch and with a quick configuration connects all the devices seamlessly.

All Projects Have a Finish Line

As I mentioned earlier, this didn’t happen overnight, nor do I feel a sense of completion. I still have light switches I would like to switch to Lutron, devices I could tell Alexa to control, and ways to turn our app-controlled devices into more passive experiences through motion detectors and geofencing.

For the holidays, I received two MyQ Smart Garage Door Openers and some Wemo Smart Outlets, both indoor and outdoor. With these recent additions, I am nearly done with my smart home conversion.

I hope this narrative inspires you to finally start your smart home project and align with a product line. In a crowded market, it’s important to make smart decisions early on before finding yourself with multiple brands of smart home products.

From the Pharmacy to the Fundraiser: My Unexpected Journey to Stupid Cancer

I’m writing this from 35,000 feet—somewhere between Austin, TX, and New York City—as I head to Toast, Stupid Cancer’s annual fundraiser. It’s been a while since I’ve reflected on how I got here, and this flight feels like a good time to look back.

When I was 15, I got my first job as a Pharmacy Technician at the local mom-and-pop Islip Pharmacy. I loved it. I loved helping people, loved the structure, and even kind of liked the hustle. That led to a job at CVS, then at our community hospital. For a while, I thought I’d be a pharmacist—until I scored a 62 in high school chemistry. Even that was curved up. I started to see that maybe my future wasn’t behind the counter, but somewhere else. Thankfully, I was also pretty good with computers. Tech quietly became my Plan B.

In fall 2009, during my fifth year of undergrad (yes, fifth), I was sitting in a Grant Writing class without a clear idea of what came next. That’s when Cyndy, a guest speaker, introduced us to the “I’m Too Young For This! Cancer Foundation,” or i[2]y for short. My dad had been diagnosed with cancer in 2005, so the mission immediately caught my attention. I couldn’t help myself—I started browsing their website during her talk and even shot off an email to the CEO asking about internships. I got in trouble for it, but it turned out to be the right kind of trouble.

Around the same time, I applied for a Community Coordinator job at the hospital where I worked in the pharmacy. It was an entry-level marketing role—perfect for someone about to earn a degree in Communications. I didn’t get it. It stung at the time, but in hindsight, I’m grateful. That “no” cleared the path to something better.

On January 23, 2010, I started an internship at i[2]y with founder Matthew Zachary. I used my PTO from the hospital to spend Fridays in i[2]y’s Lower Manhattan office, bouncing between my pharmacy life and a new world in nonprofit startup life. In April—just two weeks before Matthew’s twins were due—I got the call: a full-time offer. I accepted immediately.

The next couple of years were foundational. We were scrappy but focused. We had a vision and were determined to build something that mattered.

In 2011, we rebranded from “I’m Too Young For This!” to “Stupid Cancer.” Almost instantly, our Facebook numbers shot up, thanks in part to a bold awareness ad that took off and got hundreds of thousands of likes. We leaned into that momentum.

That same year, we took our annual conference, the OMG! Cancer Summit, to Las Vegas. With support from Volkswagen, John Sabia and I jumped into a tiny coupe and hit the road. We visited hospitals, met patients, hosted meetups, and ultimately circled back to Vegas. We’d go on to do five of these road trips over the years—logging over 35,000 miles and leaving a trail of awareness, community, and purpose. Big thanks to GM/Chevy and Michael Savoni for helping keep us rolling.

From that point on, there was no slowing down. Stupid Cancer had found its stride, and we were all in.

Between 2013 and my departure in 2016, I focused on scaling areas of the organization that hadn’t yet been fully realized. One of my proudest achievements was growing the Stupid Cancer Store—from less than $5,000 in annual revenue to over $150,000. More than just a revenue stream, our apparel became a badge of identity for our community. We even spotted it on national TV. (Shoutout to Italia Ricci for that.)

Today, as I head back to NYC for Toast, I’m reminded of the winding road that brought me here—from a pharmacy counter in Long Island to co-leading a national movement for young adults affected by cancer. The journey was anything but linear, but it was exactly what I needed.

Did you spot the @StupidCancer logo in last night’s #ChasingLife? Here’s @italiaricci modeling a #StupidCancer tee! pic.twitter.com/KVNueba9PV

— Chasing Life (@ChasingLifeTV) July 3, 2014

MZ and I also sat through hours of choppy WebEx meetings with our offshore development company and created Instapeer, a mobile app for survivors and caregivers to connect and chat about their experience with cancer. It was the first of its kind.

When I think back to just how different life was from 2010 up to my departure in 2016, there are so many watershed moments for the organization. It was an incredible ride to be on.

Tonight, I am receiving the “Stupid Cancer Recognition Award” from the current Board of Directors and staff. It’s an honor that I could not have imagined receiving when I started out in the non-profit world 10 years ago.

When I think back to my motivation for inquiring about the internship, the feeling of being a helpless caregiver prevails most. Watching dad go through surgeries and chemo. We were bound to the process. Helpless.

If you are feeling helpless, help someone.
– Aung San Suu Kyi

I love this quote.

My Supercharged Email Management Strategy

Managing multiple email inboxes has become all too real in 2019: personal email, school email, work email, your project, your other project. For years, the Gmail app was my go-to. Flipping between inboxes seemed like the best there ever could be. The thought of a native app with multiple logged-in email accounts plus efficiency?

No way.

2015 said “yes way,” in a big way, when Spark hit the app store and the next iteration of email management was finally here for both mobile and desktop. At long last, something intuitive that wasn’t the Apple Mail app. (Disclaimer: I’ve never used it. It gives me anxiety.)

Spark makes it easy to start, with a great onboarding experience to add your email accounts. Once complete, you’ll notice the emails you just saw in your other mail app roll in. This is when panic will set in, and you realize you should have never signed up for that daily horoscope newsletter ten years ago.

Fear not; I am about to break down Spark into a few easy, actionable steps to get going and make sense of the private email hell you’ve created for yourself.

Start by focusing on the core features

1. Signatures

2. Smart vs Classic inbox

3. Looking at all your emails vs sorting by inbox

4. Short and long swipes on mobile

5. Snoozing emails

1) Signatures

Every good email author needs a really cool signature, right? Right. Once you’ve added all your accounts, go in and create the variations of your signature.

Here is what that experience looks like:

To reiterate, you can create multiple signatures for multiple accounts. When replying, Spark knows which signature to add to the bottom of which email. It enables you to roll through emails like a champ without having to mess with how you sign the email.

2) Smart vs Classic inbox

Sometimes when you are presented with more than one option in life, it can make it hard to settle on just one, right? Recently, this was a usability issue in Spark with Smart vs Classic inbox. It was less than stellar to flip between the two, then they introduced a really nice on/off toggle.

Smart inbox off – Showing all emails

Smart inbox on – Showing emails that have been seen at the top. Would normally be broken into important, notifications (aka promotions), and then seen. At the time of writing this, I don’t have any new emails.

This is a super helpful mobile experience for when you’ve just woken up, come out of a long meeting, or any other time you haven’t looked at your email and are looking to cut through the fat.

3) Looking at all your emails vs. sorting by inbox

Before you get overwhelmed thinking you’ll be bombarded by all your emails, you can look at them in their entirety (all of your emails, from all accounts) or by individual accounts. This is accomplished by using the menu on the left side. It’s a helpful mechanism to focus on whichever headspace you’re in.

4) Short and long swipes on mobile

I can dominate my email on mobile with short and long left and right swipes. Here is how I have them set.

5) Snoozing emails

This is my favorite part of Spark and my motivation to share this information with you. Snoozing emails has become the key to my success as an adult who sends emails.

Whether you’re on mobile or desktop, snoozing could not be more simple. When I am at my computer, I use my ⌘+D shortcut, which instantly pulls up a similar pop up to the one below.

When snoozing emails on my phone, I am presented with the question of when I want to see the email again.

Snoozing is perfect for situations where the ball is in someone else’s court and it requires a follow up to see if the action happened and what the outcome was.

Scenario A: If I send a request out and can wait until the next day to hear back, I immediately snooze the email for tomorrow morning.

Scenario B: If I get an email that is important but not more important than what I’m doing in a given moment, I will likely snooze it for a few hours or until 6 pm when I have completed my most important tasks, emails have slowed down, and I can think about something with a clear head.

Scenario C: If I get an email that I need to follow up on, but it’s not pressing, I will snooze it until the weekend.

Scenario D: Snoozing is also great for things that aren’t relevant for days or weeks. Those emails that start out so well-intended by saying “Just putting this on your radar…”

Sorry, radar is full.

Here is how my day unfolds

7 am – Smart inbox toggle on, swiping to quickly archive junk mail.

9:30 am – Emails prioritized by immediate action, snoozing for 2 hours later, the evening, the next day, Saturday, or next Monday. Occasionally, I set a date/time for emails to reappear in the distant future. (Helpful for those “let’s touch base in a month” emails.)

10 am – Prior day snoozed emails roll in.

Mid-day – Less important morning emails reappear and are dealt with.

6 pm – Lowest priority emails roll in.

Evening – Inbox zero!

That’s it. That is my email secret sauce which keeps me rolling fast through newsletters, promotions, and solicitations right on to the real emails.

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Ready to get started with Spark and become the master of your own email destiny?

Nurture Fundraisers Using CauseVox, Zapier, and ConvertKit

Fundraising is a crucial part of a non-profits existence. The biggest opportunity for a non-profit is leveraging its community to fundraise on its behalf. The hardest part is maintaining the attention of community members and empowering them to feel confident in their efforts.

For a year now, I've been using CauseVox as my primary fundraising tool for the Testicular Cancer Foundation. I really enjoy CauseVox because it puts a lot of the controls on the admin side, rather than having to go through an account manager or some other contact on the provider side.

Exploring CauseVox Zaps on Zapier

About 6 months ago, CauseVox began teasing their Zapier beta integration. As a Zapier lover and full-blown nerd, I'd been waiting for the integration to go live to see what kind of pathways I would have access related to fundraisers. A few weeks ago, the news came through that the integration was live. Excitement ensued.

The CauseVox options are simple and to the point. Did we A) Get a new fundraiser or B) Get a new donation?

With this info, I can do a lot of cool things.

One of the main features that really (I mean really) expensive fundraising platforms up-charge for is communicating with fundraisers within the platform. Campaign updates, direct emails, drip emails, etc. There's a ton of options.

My first Zap using CauseVox is to bridge the gap between a lack of communicating with fundraisers and using an email marketing platform I live in all day long, ConvertKit.

Using ConvertKit

With ConvertKit, I can create drip email sequences to walk my fundraisers along a series of emails that convey important information, emotion, and reinforce why they are so important to our organization. (Fundraisers...if you are reading this, we love you!)

CauseVox has the ability to send a welcome email, which is fantastic. I haven't yet decided if I will keep this email active or send them all to ConvertKit for the entire email series. (On one hand, it's a safe bet that the email will always send, but on the other hand, I would love to have the open rate and click metrics that ConvertKit provides.)

Creating a Drip Email Sequence

Currently, our email series is broken up like this:

Email 1: Welcome to Fundraising

Email 2: More about CauseVox and tactical points around fundraising (includes link to proprietary PDF about fundraising)

Email 3: Where the money goes / why this is so important

Final Thoughts

I am curious to see how the response is to our new series of emails. With all communications, the last thing you want to do is be over communicative and have someone lose interest entirely. By looking at my ConvertKit open and click rates, I'll see which emails are most effective and which need some fine tuning.

My Top Influencers of 2016

Over the past year, I've accumulated several different types of email subscriptions. From Seth Godin's daily musings to Nathan Barry's drip email about his book, I've read and enjoyed them all.

Email is a tricky medium. In recent years, I've become so accustomed to unsubscribing from newsletters, that it has become second nature to skip the content and go right to the footer. GMail has gone so far as to give you the option right from the inbox.

As social media has grown and evolved over recent years, the necessity to focus on well-crafted email has declined.

There are, however, individuals doing email and doing it well. Without further ado, here are some of my top influencers of the 2016:

Nathan Barry

Get Nathan's Email

Nathan is a designer turned writer turned email software aficionado. I am in awe of his mini-empire and enjoy watching him and the company he founded, ConvertKit, grow.

In Nathan's drip emails about his book, Authority, he takes you on a wild journey which ultimately sold me on signing up for his $29/mo email platform. See my last post about it.

Paul Jarvis

Get Paul's Email

Paul Jarvis is intelligent as he is entertaining to follow. He is a veteran web designer who shares knowledge, insights, and has carved out a nice little corner of the Internet for himself. His emails span from direct marketing to step-by-step guides.

Jason Zook

Get Jason's Email

If the Internet was a candy store, Jason would be the kid in it. I am consistently impressed with his ability to get shit done and do it in creative & innovative ways. As I pen this blog post, he is writing his next book live daily on WatchMeWrite.

* Sometimes Nathan, Paul, and Jason come together to form course-making Voltron and put out some really great stuff.

Tobias Van Schneider

Get Tobias' Email

I can't recall how I came to find out about TVS, but I am glad I did. Tobias has an eye for the finer things in life and shares this through his channels. His weekend emails are interesting commentary on design, technology, pop culture, work, and productivity. As a world-class designer, everything is put together rather elegantly.

Seth Godin

Get Seth's Email

Seth Godin has been around almost as long as the Internet itself and needs very little introduction. Seth has been blogging every single day for many years now. His morning emails offer inspiration and prompt introspection. It's a great way to start off your day and can help you make decisions in life and business.

I would be remiss in failing to mention the evolving good stuff that Gary Vaynerchuk puts out every single day, seemingly on every platform. I have also enjoyed watching Casey Neistat chronicle his life in his daily vlogs.

Let me know if the comments who you subscribe to!

3 Automations to Make Year-End Fundraising a Breeze

It's that time again: year-end fundraising and the race to December 31st. While this can be the most wonderful time of the year, it's also the most tedious, data-intensive, drive-you-to-drink time of the year. Unless you have the right tools in place.

Luckily, there are options when it comes to funneling all the data your donors are generating. Enter, Zapier automations.

If you're unfamiliar, Zapier is a subscription service that connects different online apps to one another using API and other means. With a few simple clicks, you can connect the majority (read: relevant) of your apps and be on your way.

The Approach

For me, architecting my Zapier arsenal is a problem-first approach. What do I need in the future and where do I need it?

Let me pause here and give you a word of caution. With too much automation, you can enter a data redundancy wormhole, wherein you have exhausted your monthly Zap limit and reached the task limit. If you have no idea what I am talking about, great. If you're as nerdy as I am, you will be at 80% of your task limit in no time.

Without further suspense, here is my list of essential automations to get from here to listening to U2 on January 1st.

Stripe to Slack

Stripe is currently my primary payment gateway. Using the direct Slack integration, I send payment success, payment fail, and daily deposit information into an #incoming-money channel. On the Zapier side, I send customer and transaction metadata to the same channel. It's duplicative, but helpful for providing donation context in the moment. The input and output looks something like this:

If I donate $5, there will be an #incoming-money message that says "Kenny Kane (kennykane@gmail.com) has donated $5 to campaign x."

By including the customer email field in my Zap, I can very quickly send a new email, instantly, from Slack to thank or learn more about them. I also use it to look them up on social media and try to get background info on them. I typically do this for donations larger than $250. If it's an interesting email domain, I will do it for less.

Stripe to Wunderlist

One of the places you can set yourself up for failure the most in donor cultivation is the process of thanking them. For me, a Slack notification can fly by and be lost forever. To mitigate this problem, I set up a handy insta-to-do list.

Using a similar formula to my Slack message, I create a new Wunderlist task for each successful Stripe transaction. At certain time intervals (instantly – 24 hours), I check my 'Donor Thank You' Wunderlist and clear out the donations less than a certain amount. From there, I prioritize biggest donations first. This integration helps me sort through the madness of my donation notification emails, Slack alerts, and any kind of reports Stripe might give me.

Stripe to Google Sheets

I use Google Sheets to create a running table of all donations. This is helpful in running some quick analytics around donations and drawing conclusions without digging through information from multiple sources.

As you may know/come to find out, things break and I don't expect this integration to work 100% of the time. If I am creating any sort of enduring report, I would go right to Stripe for an export.

In Conclusion

The year-end season of giving can be a noisy time. By leveraging the backend APIs of your platforms, you can create a nice system of checks and balances to ensure you won't have incomplete reports, or a donor who feels like they don't matter.

These are just 3 quick automations. If you were looking to get really automated, you could use Zapier's (relatively) new multi-step Zaps to access existing information and update it, such as adding lines to your CRM.

Good luck!

ConvertKit Makes Me a Better Non-Profit CEO

What makes a good marketing email? For years, I thought it was a combination of colors and images, font types and social icons. I remember when Mailchimp released their drag and drop editor in November 2012 and everything changed for the amazing.

Four years later, I find myself running away from what I once worked on so hard on. Sending flashy emails seeking to dazzle constituents. Don’t get me wrong, I still use said editor and send branded emails, but it is my belief we’re on the verge of a new communication style in the non-profit sector that compliments the main email list.

Last year, I stumbled upon Authority & Nathan Barry and immediately went down this author, creator, entrepreneur rabbit hole. (Shout out to Nathan, Paul, Jason et al) While entrenched in Nathan’s drip email sequence about his book, I found myself looking forward to the next email from him. It was a non-annoying batch of emails that added value to my inbox every few days. What I didn’t realize was that he was actually selling me on his product, ConvertKit.

ConvertKit strips away the fancy drag and drop editor and provides you with the ability to send personalized plain-text emails, fast. Gone are the days of the bulk BCC, replaced with the ability to let my network decide on how they want to engage with me, and the organization I run.

With ConvertKit, I can tag subscribers by donation tiers, campaign affiliation, etc. What’s more, I can change up who the email comes from quickly. If I want to send the email from a fellow staff member or Board Member, it’s a two second switch before the email goes out.

What I really love about ConvertKit is that I can create links within the email that allow people to tag themselves using automations. In the past, a subscriber would have to visit a preference page to do what they can now do right from their inbox. By giving people options on what they want to hear about on the front end, I’m reducing the number of people who might go right for the unsubscribe link in the footer. If they do unsubscribe, that’s fine. "Engage or die."

Uncle Ben said “With great power comes great responsibility.” He’s right. As your ConvertKit database grows in size, you have to maintain strict segmentation of messages and resist the urge to send to everyone at once. That’s what your other list is for.

Since implementing ConvertKit, I’ve seen a ton of conversion and interest from my outbound emails. With the built in analytics, I can see who is opening my emails and interacting with them. These insights are helpful when knowing which donors to pursue, or volunteers to activate. As time progresses, I am discovering new and exciting ways to incorporate ConvertKit into my day to day. With CK starting at $29/month, I can’t help but think back to all of the Salesforce add-ons, priced astronomically, to achieve something similar.

Creating opportunity through self-service

On January 1st, I assumed the role of YNPN-NYC Board Chair. It has been a great first month, taking a 35,000-foot view of the chapter and its operations.

One of the value-adds of YNPN-NYC in the past has been a job board. Previously, anyone could post, just so long as they were a member. This was a great funnel to grow membership, engender community, and create a cycle of brand awareness and retention among employer and employee.

At the start of the year, our Board roster was a little light. Part of the “steep” learning curves of assuming my role, has been to figure out band-aids to carry the organization until we’re whole again.

As I set out to reimagine some of our tech infrastructure, including how we billed membership dues, the job board was a priority to sort out. At the very least, YNPN-NYC must continue to support the nonprofit community which we aim to serve in this capacity.

Through a bit of googling, and some luck, I stumbled upon JobBoard.io. It’s a turnkey solution that allows employers post jobs, candidates to find employers, and board operators to collect a fee for the service. For YNPN-NYC, this is found money around-the-clock.

What really sold me on the platform beyond the customer service from its CEO was that it’s inherently self-service was and we could brand it. Now, jobs.ynpn.nyc is the place to start your nonprofit career in New York City.

Sure, there are other big names out there. How cool would it be, though, to start a job interview talking about your mutual connection through YNPN-NYC and doing good in NYC.

Since the implementation of the new job board, we’ve had 36 jobs posted. Postings begin at $25 for a 30-day listing. Employers have the option of featuring the post for an additional $25. To celebrate, the launch of the board, I utilized the embedded couponing functionality. Until the end of the month, you can save 25% by using coupon code “launch” at checkout.

I’ve enjoyed watching the jobs come through during the work day. I have an integration through Zapier that posts to my Slack channel in real-time. There’s another automation that tweets new job postings to @ynpnnyc.

Thus far, postings have translated into $820 in found revenue for the organization that will be reinvested into expanding our reach and programming for members.

I’ve learned from this experience that sometimes the best way to capitalize on opportunity is to put it in the hands of the person on the other end of the transaction.

Why We Switched to Recurly at YNPN-NYC—and How It’s Already Paying Off

When I stepped into the role of Board Chair at YNPN-NYC earlier this month, one of my first priorities was upgrading our recurring membership payment system. We’d been using a mix of PayPal and SquareSpace purchases, and while functional, it lacked the modern tools needed to streamline operations and improve member experience.

My familiarity with Recurly actually goes back to 2015, when I was a customer of a SaaS platform that used it to manage their subscriptions. I had a good experience—especially with the added bonus of a discount—which left a lasting impression. That experience stuck with me when I started looking for a better solution for YNPN-NYC.

The Payment Patchwork We Inherited

Historically, YNPN-NYC managed recurring dues through PayPal. Then, after a website redesign, new memberships were processed through SquareSpace and synced with Mailchimp. That approach kept the process seamless on the front end but fragmented things behind the scenes. By the end of 2015, we had members split between PayPal and SquareSpace, with no central system to manage them.

Why Recurly?

I needed a solution that was:

• Low-friction for users

• Self-managing on the backend

• Elegant and modern

Recurly’s ecommerce-like experience won me over: members check out once, and the system handles renewals annually. Simple, clean, and scalable.

One of the biggest wins? Recurly syncs active subscriptions to Mailchimp twice a day. No more manual exports. And if someone cancels, they’re automatically removed from the list. Even if that integration didn’t exist, I could have used Zapier—but luckily, I didn’t need to.

Implementation

I approached this rollout with a “day-one” mentality—something I’d recently done with a CRM overhaul at Stupid Cancer. I knew legacy members might be affected, but new signups wouldn’t feel a thing. The setup process for Recurly took less than 30 minutes, and once everything was configured, I pulled down the old form and waited for signups to begin.

January was the perfect time to launch—right in line with New Year’s resolutions—and the response was strong from day one.

After verifying that everything worked, I uploaded legacy members into the new Mailchimp list using their name, email, and membership anniversary date. That allowed me to begin mapping the past to the present.

Migrating Legacy Members

Recurly adds two private fields to Mailchimp. Since we only offer one plan, everyone has the same data in those fields. That made it easy to identify which 2016 members were new and which ones were legacy holdovers.

With Mailchimp’s segmentation tools, I created lists of legacy members based on their anniversary date. That allowed me to identify those who were expired but hadn’t yet been imported into the new system. I haven’t finalized how many reminders these members will get before being moved to the inactive list, but the goal is clear: win them back.

We’re experimenting with coupon codes and other incentives to reactivate lapsed members. Some may not even realize their membership expired. While we know we won’t win back 100%—life moves on for many—it’s worth the effort to retain who we can.

Why Members Love It

What makes Recurly so effective is how it puts the power back in the hands of members. Seven days before their renewal, they get an email reminder. They can cancel, update their billing, or do nothing and let it renew. If a payment fails, Recurly will attempt to fix it automatically (like updating an expired card) before notifying the member. It’s hands-off but thorough.

Looking Ahead

Migrating a membership base sounds like a heavy lift, but modern tools make it manageable—and worthwhile. Retaining a member is always cheaper than acquiring a new one. But more importantly, not spending time managing things that can be automated is a win for any organization.

The Results (So Far)

In the first 18 days of launching Recurly, we had over 75 new members sign up—strong validation that this was the right move.