Lessons from 20 Years of Fundraising and Marketing
Today marks 20 years that I’ve been in this industry. 🥺
Twenty years ago, on June 7, 2004, I walked into my first day in a new job and into a new world of marketing and fundraising for nonprofit organizations.
Just a few weeks prior, I had no idea that working with nonprofits was even a career option for someone passionate about marketing and making a difference.
At the time, I was running a skate company (Pancho Longboards – that’s a story for another time!) and working in marketing at a university.
Since then, I’ve worked in 8 different roles across two companies – first at Masterworks – a marketing agency, and eventually founding Imago Consulting to advise leaders and organizations.
In those two decades, I’ve covered quite a bit of ground, from project management to client service, digital, strategy, media, analytics, and innovation. I’ve built teams, led teams, and advised teams. I’ve enjoyed every part of this world, but my favorite is when I get to come alongside leaders to help them see a vision for the future – their Imago – a future that will be, but does not yet exist.
This week, I sat down to reflect on the lessons I’ve learned these past two decades.
My initial idea was to share 20 lessons in 20 years, but I hit twenty and just kept going. So, without further ado, I present to you 40 lessons from 20 years in fundraising and marketing.
40 Lessons from 20 Years in Fundraising and Marketing
1. Lead with trust. They say trust is earned, but life is better when you lead with trust. Equip people and assume the best.
2. Attack problems, not people. Life is a series of problems to address, puzzles to solve, and opportunities to seize. When issues come up, come together and attack the problem side-by-side.
3. Content before connection is worth less. I’m a teacher at heart, but when connection and belonging are missing, the best content in the world isn’t going to be received well. Just ask my wife the middle-school teacher.
4. There is nothing new under the sun. The more I’ve studied history, the more I’ve realized that there really is nothing new under the sun. The writer of Ecclesiastes had it right – “What has been will be again, what has been done will be done again.”
5. Everyone is a 10, somewhere. Environment matters, and context matters. I’ve seen some of the most talented people struggle in contexts that don’t support who they are. Bonus: Don’t assume you are as good or as bad as your present circumstances indicate. A simple change of context can make a world of difference.
6. Be open-handed. Be open to possibilities. Take meetings where you don’t see an obvious outcome, but your gut says yes. Some of the best moments in life have come from stepping into a situation and being open-handed and generous.
7. The greatest players have the deepest flaws. I don't know if this is universally true, but in my experience, the most talented folks have some of the biggest shortcomings. This is not bad – we are all flawed. However, it requires discernment and deftness to maximize strengths and minimize weaknesses.
8. The best kind of leader is a self-aware one. I learned this from author Patrick Lencioni, one of the greatest management minds of our day. There is no “ideal” leader or leadership style. There are as many leadership styles as there are leaders, and we’re all flawed (see point 7). Self-awareness is key – understanding strengths and weaknesses and leading in light of those. My friend Terry wrote a book about this.
9. Know your strengths. One of the best management trends over the past 20+ years has been the focus on strengths-based leadership. Tools like the Working Genius encourage individuals to understand and lean into their strengths. Which strengths have you been given, which have you developed, and how can you design your life to maximize those?
10. Know your weaknesses. We all have blind spots, areas of weakness – things that drain us. The strengths-based focus is not an excuse for ignoring your weaknesses. Understand those areas where you don’t excel, and find ways to minimize those weaknesses.
11. We need others. No one person has “it all,” whether that be talents, skills, connections, or knowledge. And the better we understand our strengths and weaknesses, the more we should recognize our need for others. Working Genius has helped me see when I try to ignore others' strengths and don’t understand my own.
12. The lone innovator is a myth. How often does a leader get all the credit for leading innovation? See Steve Jobs. Elon Musk. Jeff Bezos. Martin Luther. Leonardo da Vinci. Michaelangelo. We love to put people up on pedestals. But in every case, when you look into these “hero” stories, you find out that they had collaborators around them, often dozens of them.
13. Don’t mistake activity for progress. I learned this from Steve Woodworth, my boss, partner, and mentor for many years. There is a difference between “busy” and “productive.” Don’t get them confused.
14. Innovation is ancient. I used to think innovation was the realm of “new” things. New ideas, new breakthroughs, new tools. But when you recognize there is nothing new under the sun, you realize you can learn much more about innovation from history than from the present day.
15. Cultivate an outside mindset. We all have a problem – the more expert we get in any given field, the more confident we become in our ability to solve problems, but also the more narrow our perspective becomes. This is a problem when we face difficult challenges and need breakthrough innovation. The antidote is to cultivate an outside mindset.
16. Invest in diverse relationships. We all live in bubbles of our own making. That is not necessarily bad – we crave community and tend to be attracted to those we share things in common with. But when we realize that we all live in bubbles, we can seek to break out of those bubbles and invest in diverse relationships.
17. Your mission is not the same as your model. The mission doesn’t change, but models and methods must change to remain relevant and effective. The graveyards of history are filled with organizations that pioneered one way of doing things (method) but failed to transition to the next model. Case in point – Look no further than Blockbuster.
18. Life is 10% what happens to me, and 90% how I react to it. I learned this from Coach Curci in high school and have always remembered it. Turns out it’s a Charles Swindoll quote (apparently, there’s now a book). It’s shaped how I respond to the good and bad things that have happened to me in life.
19. Journal. Whatever you are going through right now, however strongly you are feeling – you won’t remember it in a few years. At least, not accurately. Write it down. What are you going through? What are you thinking? How are you feeling? It’s a wonderful way to work through stuff, and you can go back when you have some perspective.
(Bonus: If you are a verbal processor, record yourself journaling out loud and use AI to transcribe it).
20. Ask for help (reciprocity is a beautiful thing). There are many reasons we don’t ask for help. We don’t want to admit we need it. We don’t want to burden others. But asking for help can be a gift to the one being asked as much as it is to the asker. Reciprocity is a beautiful human quality that brings us closer together.
21. Don’t judge others because they don’t have your strengths. At one point, I realized that I had a tendency to judge people based on whether they shared my strengths. We tend to overemphasize our strengths and take other strengths for granted. See others for their unique gifts and strengths.
22. When you start a thing, you won’t know what you’re doing. And that’s OKAY. In every job I’ve ever started, I’ve wondered, “Why me? Can I do this?” You never know when you start. The only way to find out is to do it and give it time.
23. Experience takes time, but you can pray for wisdom. I learned this from executive coach and mentor Bobb Biehl. When I was a young executive, I asked him, “How can I possibly be expected to advise these clients who are decades more experienced than I am?” He responded, “Dave, experience just takes time, but you can always pray for wisdom.” I’ve never forgotten it.
24. Feedback is more important than shipping. “Ship it” is a common idea in innovation. Get it, whatever “it” is, into the market as quickly as possible. This has some truth, but only if you get feedback and learn. Shipping without feedback is a tragic waste.
25. The difference between who you are today and who you will be in five years is 1) the books you read and 2) the people you spend time with. This is a paraphrase of a quote I came across years ago. I review it several times a year to prompt me to reflect – who am I spending time with, and what am I reading?
26. Be yourself. The better we know ourselves and accept who we’ve been created to be, the more we can be authentically us. Trying to be someone else is exhausting. You won’t be everyone’s cup of tea, and that’s fine.
27. Priorities always have trade-offs – get yours in the right order. Years ago, at a marriage retreat, a speaker shared how he was considered “behind” in his career because he prioritized his marriage and family. That was the first time I realized that I couldn’t have it all, at least not all at once. Force-rank your priorities and recognize that they come with trade-offs. My priorities are faith and family, then work, then everything else.
28. In marriage, fight for each other. There isn’t much more that brings a marriage closer together than when you fight for your spouse. Heather fights for me, and I fight for her. “You and me against the world” is a powerful glue. I learned this from my friend Dan Serdahl.
29. Parenthood is a gift. I once heard a marriage counselor say, “People think marriage is about love, but marriage teaches you how selfish you really are.” With two kids at the time, I remember thinking, “No, marriage is just the warm-up – PARENTING teaches you how selfish you really are!” For me, there has been no greater gift than parenting. It’s changed who I am. How I care for others. How I lead. Parenting teaches you a lot about yourself and about others.
30. To be known and loved is a beautiful gift. The full quote comes from author Tim Keller and is too good not to share:
“To be loved but not known is comforting but superficial. To be known and not loved is our greatest fear. But to be fully known and truly loved is, well, a lot like being loved by God. It is what we need more than anything. It liberates us from pretense, humbles us out of our self-righteousness, and fortifies us for any difficulty life can throw at us.” – Tim Keller
31. All miscommunication is a result of differing assumptions. At the root of any miscommunication are two different sets of assumptions. Bobb Biehl taught me this, and I’ve seen it time and time again in my life, in my work, and in my marriage. His full quote is, “All miscommunication is a result of different assumptions, and leads to frustration, pressure, and tension.” So true.
32. All planning begins with the phrase “at this stage in our development.” This is another Bobb Biehl gem; I take it as a reminder that we are all at different places and stages, and what is right in this season may not be right for us in the next. Every time we seek to create a plan or decide what to do, we should ask ourselves, “At this stage in our development, what should we do?”
33. Be curious. Follow your curiosity. Related to cultivating an outside mindset, following rabbit trails can lead to unexpected and new places.
34. Ask stupid questions (because they probably aren’t). I can’t tell you the number of times I’ve been in a setting where I’ve asked what I thought might be a stupid question, and it turns out others were wondering (or confused or curious) about the same thing.
35. Innovation is managing the present while inventing the future. And leaders all have a bias one way or another. You may be more future-oriented or more oriented to the present day. Either way, the task of leading any organization is managing what is happening today while looking down the road and inventing the future.
36. Discipline is more important than talent. I’ve observed this in people I admire who are talented but develop extraordinary discipline. In my world, I think of Tom Harrison, former CEO of the Russ Reid Company. In sports, think of athletes like Michael Jordan and Kobe Bryant. Talent is one thing, but what stands out is their discipline.
37. People become how you treat them. If you treat someone with trust, open-handedness, and respect, they will be trustworthy, open-handed, and respectful the vast majority of the time. Likewise, if you treat others with suspicion, hostility, or disrespect, over time, they will become what you fear (whether or not they were that in the first place). What you expect of people shapes how you treat them and who they become, at least in your eyes.
38. Don’t compare your beginning to someone else’s middle. This one comes from Jon Acuff, a NY Times best-selling author and INC Top 100 leadership speaker. I’ve heard variations on this quote over the years, but when I heard it from Jon, it really stuck. It’s so easy to compare ourselves to others who are years ahead of us, and it can lead to despair, discouragement, and jealousy.
39. Take care of your health. Not much matters when you don’t have good health. We can’t control everything, but our lifestyle and decisions greatly impact our health. For me, that means watching sugar intake, limiting treats to weekends, getting at least seven hours of sleep a night, stretching and strengthening three times a week, and withdrawing to recharge and rest.
40. We’re all on a journey of understanding who we were made to be, the context we’ve been placed in, and what to do in that intersection. Each of us has gifts, strengths, and weaknesses. We’ve been wired to think and act in certain ways. But we also live in a specific context. We were born at a particular time in history. We have lived experiences that have shaped who we are, both the good stuff and the bad – often even more so the bad. Based on who I am and what context I’ve been placed in, what does faithfulness look like?
💡 Takeaway: Twenty years in, and I am blessed. Some days, it feels like I’ve come so far, but most days, honestly, I feel like I’m in the starting gate of life. I used to wonder when that would change, but now I hope it never does. I think it means I’m challenging myself with new things, learning new things, and growing.
I’m looking forward to the next twenty years, and I’m grateful to you for being a part of this journey.
Until next week… Surfs Up! 🌊
- Dave
P.S. The first draft of the book is complete! If you’ve been following the journey, I’m writing a book about how nonprofit leaders can take advantage of building sustainable recurring giving income in the Subscription Economy. If you’re interested in being a part of the launch team, contact me.
About the Author | Dave Raley
Consultant, speaker, and writer Dave Raley is the founder of Imago Consulting, a firm that helps non-profits and businesses create profitable growth through sustainable innovation. He’s the author of a weekly trendspotting report called The Wave Report, and the co-founder of the Purpose & Profit Podcast — a show about the ideas at the intersection of nonprofit causes and for-profit brands.
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