Catching Up

Rob: How have you been doing?

Morgan: Doing well, I think we last spoke in the summer, right?

Rob: Yeah, looking back, it seems like June was our last conversation.

Morgan: A lot has changed since then, especially on the business front. We dove deep into user feedback and realized our positioning needed a shift. Initially, we were focused on creating memory walls to preserve the memories of lost loved ones, which resonated well at certain times—immediately after a loss or much later for sharing with future generations. However, there was a gap when the loss wasn't so recent or immediate.

Rob: Right.

Morgan: That's when we noticed the unique value of our support registry. It became apparent that our services were incredibly valuable immediately following a loss, but there was this gray area, especially when dealing with terminal illnesses or prolonged treatments. The focus on death felt insensitive in these contexts, prompting a significant rethink and rebranding of our platform.

We transitioned to a broader approach, aiming to support families through various tough times, not just the loss of a loved one. This repositioning led us to develop a more supportive and less intrusive model, where we could offer help without adding to the family's burdens.

When we relaunched in October 2023, the response was overwhelmingly positive. The uncertainties and sensitivities around our previous focus diminished, and we saw an immediate alignment with our users' needs. Our platform became a place not just for remembrance but for active support in various challenging life situations.

Rob: That's impressive. It must feel rewarding to see such a positive shift and real user engagement with the new direction.

Morgan: Absolutely, it's been a significant and fulfilling pivot. We're now more aligned with our users' needs, providing support that's both timely and sensitive to their situations.

Rob: You're building a few things, then putting them to market, assessing what people use, focusing here, adjusting the messaging there, and it just completely changes everything, right?

Morgan: Yeah, exactly. In the beginning, after launching our product and starting to receive feedback, our workbench started to overflow with stuff. We reached a point where we needed to step back and acknowledge that things were only getting more complicated and not necessarily working. So, we decided to review what we had learned, leading us to make a significant pivot—a 180-degree turn—new brand, new logo, new messaging, new product, everything was unrecognizable.

Rob: 180.

Morgan: Exactly, a complete turnaround. And we didn't stop there; we pushed further to realign our incentives with families, reimagining our business model. We even considered what a private equity firm or a competitor seeking to disrupt us would strip away to cut the excess. Our big competitors are GoFundMe, Meal Train, and CaringBridge. We aimed to integrate the value they offer into one comprehensive tool, addressing their shortcomings, like Meal Train's expensive features and platform fees.

Rob: Okay.

Morgan: We eliminated feature paywalls and platform fees, offering everything upfront without cost. We observed GoFundMe's focus on financial support and allowed families the option to turn that feature on or off. We also decided to subsidize credit card processing fees, aiming to offer the industry's lowest rate, which we fund out of our pocket.

Rob: Yeah.

Morgan: By addressing these aspects, we created something streamlined and modern. We eliminated numerous features that were burdening our system, resulting in a snappier, more user-friendly product.

Rob: That’s impressive. The rebrand and the new website look fantastic. It seems completely new, fresh, and relevant.

Morgan: Absolutely, it's a totally new product, unrecognizable from before.

Rob: Very exciting. Thanks for sharing this and for catching up. By the way, have you had a chance to check out our new site?

Morgan: The site looks incredible, very sharp and aesthetically pleasing. I haven't delved into the videos yet, but the overall design caught my eye. Great work.

Rob: Thanks, Morgan. We're actually planning another overhaul soon to take it even further, despite just launching this version three months ago.

Background

Rob: I'm interested in the personal journey that has shaped your management principles. Many executives say you should be the "dumbest person in the room," for example. I'd like to understand where your principles originate and how they influence your leadership. Where does this all stem from for us as managers, as product leaders? In your personal life, Morgan, your experiences will differ from anyone else's I talk to, which makes your perspective unique. The core principles of good management are well-known. However, what validates these principles for you is what intrigues me the most. To give an example, I spoke with a founder and early employee at Instacart, who emphasized humility in business culture. His understanding of humility wasn't about being timid but being willing to voice opinions, even at the risk of being wrong. He shared a deep, personal story about his father that really shaped his approach to interactions with others. That's the kind of depth I find fascinating in these discussions. 

Let's start with a bit about your background, not just your work history, but also where you're living and your life experiences.

Morgan: Currently, I'm in Oahu, Hawaii. We moved here a year ago, embracing remote work, especially after a challenging health period with our youngest daughter. This experience prompted us to reevaluate our priorities, focusing on family and making memories. My route into software wasn't straightforward—I was an early childhood education major who got into tech through designing coffee labels. This led to various projects, from inventory management to website editing, eventually leading me to software engineering. And it was an acquaintance who introduced me to Ruby on Rails, teaching me not just to build web applications but to apply engineering principles broadly in life. He emphasized the mindset of solving problems as an engineer, which has stayed with me and influenced how I approach various challenges, both professionally and personally. Starting from simple tasks like changing a button's color to broader business strategies and personal relationships, I've applied this problem-solving approach throughout my career and life, leading me from the coffee shop to partnering in different ventures and shaping my perspective as a manager and leader.

Rob: Man, that's awesome. So you go from the Consulting thing to being embedded in a few companies now you're at support now. You've been there for how long?

Morgan: About 3 and half years. We have a product and lots of contractors, but to really get this done, as the founder said, we need to become a real business. So, he asked who could come work with us? And there was a week between when he asked me that, and I put together this list for him. And I sent it back saying, "Let me know." And, by the way, I'm planning a transition out of my current company. Could I throw my hat in the ring? His response was simple: "Let's have that conversation before I reach out to any of these people."

During one of my final trips to Mexico, in a rural village during Day of the Dead, I saw the space that Mexican people create in their lives around the topic of life, legacy, and death. It was striking. They had ripped up the street, lined both sides with simulated graves, decorated beautifully with orange flowers and pockets of fire. It was captivating. This made me think of my conversation with Scott, the co-founder, about building this product. I realized Mexico has something figured out here that we don't in America, which is creating space when life's tough times happen.

As we walked down this path, I realized we were more poorly equipped than I thought. As we learned and got more user feedback, it became clear there's more to explore. Perhaps helping people become comfortable with mortality starts with just being sick or dealing with bad stuff happening. We've seen a cultural movement of people doing similar work, pushing for real, actionable support for those going through tough times.

Rob: Yeah, and if you don't mind me asking, what's your daughter's name?

Morgan: Rowan

Rob: Rowan, okay. So, Rowan's experience and the experience you and your wife had, that must make SupportNow pretty personal for you.

Morgan: It's been heart-wrenching but also encouraging. Some days are emotionally draining, but I find it encouraging that we're trying to make a difference. My family's experience, especially my daughter's health challenges, makes me reflect on how we can do things differently. My daughter, who had a kidney removed, has to have scans every three months due to a genetic disorder that causes tumors. This personal connection to health and mortality drives my commitment to what we're doing at SupportNow.

Rob: Wow…

Morgan: I can tell you every time we have scans, around our house, the days surrounding them get pretty tense, and how I love and serve my wife, my family, the conversations we're having with our kids, are all different because of the time and energy spent trying to make sense of this.

Rob: Thank you for sharing all that, and I appreciate you sharing about your daughter too. Sorry you have to deal with that, but it sounds like she's healthy now, yeah?

Morgan: You would never know by looking at her. Yeah, she is just full of life. She's healthy.

Rob: That's great. 

So, the transition from Me Alma to SupportNow happened in recent months, right?

Morgan: Yeah.

SupportNow Culture

Rob: And you said you made that transition and actually launched in October last year?

Morgan: About six months ago. So Q4 was when the new product was fully live. I wouldn't say we've sunset the old product yet, but activity went to zero on the old thing, and it was the first full quarter of the new product.

Rob: Nice. And so, when I look at SupportNow, I've talked to you about this before, but basically seeing that output from the previous output, which seemed like a solid idea, product, service, but the transition to SupportNow and the way it's been executed, the way it looks, the messaging and branding, and the way you even speak about it seems a lot more focused and clear. I'm really interested in the culture that leads to a product that has that kind of clarity.

Morgan: Sure.

Rob: Given that you're an executive at SupportNow, and I'm sure there are others, I don't know the full team size, can I ask that?

Morgan: There are three of us on the leadership team, and the total team, with a mix of full-time and part-time members, is around seven or eight.

Rob: Okay, nice, pretty lean. How are you creating the culture you want?

Morgan: Yeah, well, I think the first thing about culture is defining what great culture is. For me, a great culture is where people could work anywhere but choose to work here. The 'could work anywhere' part is important because you need to be good at what you're doing. I think where teams struggle with culture, some of it could be just straight-up performance. You have people who aren't good at their jobs, and that makes life hard, especially when you have others who are good at their jobs. A mentor of mine said you typically have A, B, and C players. A players love working with A players, and B players can be coached up, but C players will never become A players. As you start to add B and C players to your team, your average drops, making it hard to get things done.

A great culture is where people have options but choose to be here because the choice is important. You could do something because you want to or because you're told to, and usually, doing something by choice is more fulfilling.

We can only create conditions where culture can grow and become healthy. It's a mix of when we're trying to expand and when we're pruning things that don't belong. We want to create a place where people are the best in class but choose to be here because they're motivated by more than just money. They're here because of personal motivation, intrinsic values, and a sense of direction. We're trying to ensure we're defining success together, working on the same goals, and that creates a culture where people are aligned, even through tensions and disagreements. It's about trust, expertise, and aligning on our goals to move the business forward or make it healthier. It's a continuous process of making choices, being self-aware, and inviting open, honest feedback to foster a healthy, productive culture.

Rob: There's so much that I find extremely interesting. I love some of those analogies, especially the garden one. Creating the right environment also means encouraging the growth of weeds and knowing what is a weed and what is a fruit or a vegetable that you want. There's a lot of real gold in that analogy; it's very well stated.

Morgan: Yeah, there's some judgment there.

Rob: What's interesting to me is the way you touched on trust at the end. The idea that anyone can come to you as a leader and speak to you, especially considering you admit you're an “aggressive person” in some of these rooms. Maybe "aggressive" isn't the right word. What did you...

Morgan: I think "aggressive" is how I hear it. And I think some people might say, 'You're just passionate, you're just kind of intense,' and then I think others might say, 'You're stubborn.' So, there's a spectrum of words you could use to sum it up. I would say there's definitely a deliberate force with which I tend to bring ideas. I justify that because living with intention is really important to me. So, if I'm going to come with an opinion, I'm usually going to have thought about it quite a bit.

Rob: Strong opinions loosely held, right?

Morgan: Yeah, that's right.

Rob: My question about that is because that's a big part of culture, having leaders with a passionate view about something is very important. But it's also really important to have the right people around you who can challenge those things and don't feel like they can't challenge those things. Have you ever read "Creativity, Inc."? It's like my work Bible.

Morgan: Mm-hmm.

Rob: I just love so much about the principles talked about in there. One of them is the open door policy. Every company will tell you there's an open door policy with its leaders, you can talk to me whenever you want, my door's always open– but he says in that book, and I'm paraphrasing, you have to go open people's doors because they're not going to talk to– maybe there's a correlation here between what you're doing with SupportNow and how you build this culture of open communication. It's like, in SupportNow's role, it seems like you're trying to create a space where people can contribute because they're made aware of needs before they come to ask for help. I'm wondering how you encourage people that it's okay to challenge the leaders. It's very hard for people to do that, especially if they feel like their job is on the line. They just want to be a team player. But if I know more about this than Morgan in this case, and he might have a strong view about it, but I know more than he does, I need to be able to talk to him about it. If you're not willing to accept that as a leader, then that's a problem. But it doesn't sound like that's a problem for you. The work kind of speaks for itself, that you're able to do this pivot that y'all did last year in such a short period of time and launch it, speaks to a group of people that understand they can challenge things and they can move forward with leadership that will accept that feedback. So, what do you do to give people that confidence more than just saying that you want it?

Morgan: Yeah, so one thing I would say is the people who are bringing me things might not feel what you just said about always being open to feedback. Sometimes, you are banging your head against the wall in a conversation, and it's tiring. You're all over the place emotionally and with your thoughts, and by the end, you might feel like the outcome wasn't a win, creating a sense of fatigue. Personally, fatigue doesn't deter me much; I can push through it for extended periods, which might not be the case for everyone. Understanding the people I'm working with—whether the fatigue weighs more on them than the outcome—is important.

When reviewing a software engineer's code that required several rounds of feedback, I recognized the discouragement that can come from having your work critiqued. After resolving the issues, I made sure to point out what they did well, especially their persistence. This acknowledgment is part of giving genuine praise.

Admitting when you're wrong is crucial too. I actively look for my mistakes to maintain trust. Even though it's challenging and uncomfortable, it's necessary for building a reliable leadership image. This aspect of leadership—owning up to your errors—is like making withdrawals from a trust account, so you need to ensure you're also making deposits.

Owning your responsibilities is another critical element. If people can't rely on you to excel in your role, it's challenging to establish a foundation of trust or to give meaningful praise. When someone who isn't competent in a certain area gives praise or criticism, it may not hold much weight.

The concept of '80% good is enough' is where many leaders, including myself, might struggle. If you're overseeing a project and the proposed solution gets us 80% there, it's important to let it proceed without insisting on perfection. Allowing team members to own their contributions promotes trust and empowerment.

When someone brings an idea that's 80% there, I encourage it, perhaps with a few pointers for consideration, but ultimately, I let them take the lead. This approach boosts their ownership of the project and their confidence in their abilities. When team members feel their ideas are valued and they're trusted to execute, it fosters a more innovative and committed team environment.

In the end, when a team member presents an idea or a project that surpasses my expectations, it's a testament to effective leadership. It shows that the team can excel independently, and my role is to support and advocate for their work, ensuring it's recognized and valued.

From Manager to Leader

Rob: That's when you stop being a manager and start being a leader. There's a real difference between those two things, and I love that a mentor of mine would always say you have to place the authority where the most information is. He was always talking about how your job as a manager or a leader isn't really to make decisions but to disseminate the ability to make decisions wherever the most information is. That has resonated with me for so long, and I hear that in a lot of what you just shared. It's like you saw them come to you with something, and instead of thinking, "I'm the person in charge here. I need to redline this so it's coming from me," you advocate for and elevate their work, and they just feel amazing, and you become a fan of the work they did...

Morgan: Right.

Rob: Which is sometimes fun to be in the seats, right?

Morgan: Yeah, just cheer them on. Honestly, who's the guy at the football game having the most fun? It's the guy who owns the stadium, who's like, "Everybody here is here because I own this," and of course, did that person work the hardest? Absolutely not. They're watching multiple games at once, the interaction between the teams, the symphony of other stuff happening, the crowd, the vendors and merchants. There are so many layers to the game happening in the stadium. If you've done it well, and everyone involved at each level feels like they are participating and winning, that's amazing. The dissemination of information is huge; if people haven't been given enough information to be successful, or if there's unhealthiness at the leadership level, it's damaging.

Rob: That is what's fascinating. What makes for a good business relationship, culture relationship, is the same thing that makes for good friendships, mates, whatever. It seems overly simple, almost like a cheat code, because you'd think it needs to be more complex. But like anything, the way you get good at things is by doing little small things all the time. Like a friend of mine who's a writer...

Morgan: Yeah.

Rob: He says the hard thing for people isn't writing; the hard thing is sitting down to write. Everyone knows how to write, but sitting down to write is the hard part.

Morgan: Yeah, or it's at least the detail we miss.

Advice to Leaders

Rob: But what kind of advice would you give to someone entering a role similar to yours at SupportNow, wanting to develop a culture that leads to proud products? What's one piece of indispensable advice you'd offer from your experience?

Rob: I love how you describe velocity, about direction and speed. It frustrates me in consulting, especially with large companies that hire consultants because they can't get anything done, which is ironic. What usually happens is leadership deliberates so much on decisions that they could have tried several approaches and discarded what didn't work, advancing much more. But they get bogged down in proving decisions through surveys, ratings, focus groups, and such, leading to indecision. They disseminate decision-making to hedge bets, so when things go awry, they can blame external factors like "Our focus groups led us astray," or something similar.

Morgan: One thing as you're sharing that I noticed is it takes a lot of courage to propose something that might kill your job. It's bold to step up and say, "I think this is the right move, and if I'm right, will you move me somewhere else in the organization?" Many decisions boil down to how they impact me, my team, my job, etc. As organisms, we tend to want to grow and expand, so my natural disposition in front of a team or board is to protect what I have and ideally get more resources to grow. But in technology, where things change rapidly, it's naive to think last year's decisions will serve us today, even if it might mean cutting 30% of the organization. Who's incentivized to bring that axe to the meeting? It often takes not just courage but a lot of privilege to speak up, especially in a goodz culture, because I know I could find another job. If speaking up might make my role less necessary, I think, "What's the worst that can happen? I find another job with better pay." The stakes aren't as high for me.

But it's different for people who don't feel that empowered, who may not have as many options. I need them to speak as if they are empowered because those who do are rare, and I value them immensely. I would want to bring such people with me wherever I go, forming a kind of dream team with that level of courage and competence.

Creating a healthy culture is crucial. If meetings constantly end with unsaid important points, that's indicative of a culture problem. Part of my shift from consulting to being part of a team was to build enough credibility so that when I stand up and challenge a plan, it's taken seriously, not just dismissed like a consultant's suggestion might be.

I'm hired to say what needs to be said, even if it's uncomfortable, as long as it aligns with the organization's objectives. But when there's a disconnect between our stated objectives and the company's actions, that's when tensions rise, and I start questioning if my presence is enabling unhealthy behavior. It's then on me to reassess my role and the impact I'm having.

Rob: Yeah, okay. I feel like we could just talk for hours, but...

Morgan: It's definitely a lot; you definitely cracked it open.

Rob: There's so much gold in there. Thank you for taking this time; it's really nice to hear from someone who has a clear way of speaking, and the analogies actually are very powerful. Thank you for that.

Morgan: Awesome, appreciate it. Until our next conversation…

Rob: Indeed.

Closing Takeaways

1. Culture Development: My takeaway here is the profound understanding that culture is the bedrock of any thriving organization. Just like in a garden, you can't force growth, but you can cultivate an environment where growth and health coexist. This analogy resonates with me, emphasizing that while we can't control every outcome, we can nurture a setting where positive, organic development is possible.

2. Manager Becoming Leader: The transition from manager to leader is a journey of empowerment, not just for oneself but for the entire team. It's about placing trust in your team's capabilities, allowing them to own their projects and ideas. This approach not only elevates their work but also instills a sense of pride and ownership. It's a reminder that leadership is about advocacy and elevation, not control.

3. Moving Quickly with Direction (Velocity): The concept of velocity, combining speed with direction, strikes a chord with me. It's a powerful reminder that action without purpose can lead us astray, but when we align our pace with our goals, the path forward becomes more impactful and meaningful. This insight encourages me to not just move quickly but to move with intention, ensuring that every step takes me closer to my objectives.

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