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Coach’s Corner w/ RJ Talyor



Karen Mangia

Today on Success from Anywhere, we'll meet a swimming coach and serial entrepreneur who knows how to navigate being thrown into the deep end. He's an expert on the future of marketing and an entrepreneurial coach whose clients swim laps around their competition. Please join me in welcoming Operating Partner at High Alpha, RJ Talyor.

RJ Talyor

Thanks.

Karen Mangia

On the show, because we talk about the future of work, I like to ask every guest what was your first paid job and how did that job inform or inspire your career trajectory?

RJ Talyor

My first paid job was as a locker room attendant at the Riviera Club. And for those of you who aren't familiar, it was a swim club that was built in 1933 and nothing has changed since. My job was to clean the toilets and mop the floor. A lot of times the maintenance people would need help doing other stuff, so they would grab me to trim bushes, take trash out, paint stuff—whatever. I was 14 at the time. Honestly, that was a great job because it was just a humble start. I wanted to graduate out of that job into other jobs at the club, which I think you would level up to a lifeguard or working in the snack shack, those types of things. But I was cleaning toilets and dirty diapers and whatever else.

I think it was an interesting starting point for a lot of things. As I tell people and I think of myself, I'm only good at hard work. That's it. I'm not the smartest person that ever was, but I will work hard.

This has kind of been my little secret: working hard at that job gets you to the next job. And, you know, there's nothing glamorous about some of the work that needs to get done. People want to offload that or outsource it. If you're the one cleaning the toilet, then you get the credit and move on to the next more glamorous thing.

Karen Mangia

Your job description at the Riviera club sounds a lot like the job description for an entrepreneur.

RJ Talyor

That's about right.

Karen Mangia

Speaking of which, how does an English major go into the world of entrepreneurship? That seems like an unlikely path. Tell us more.

R.J Taylor

I have an English degree from undergrad. I have a master's in creative writing from Purdue. I was always really passionate about reading and writing and wanted to pursue that personally. In addition, I was really entrepreneurial in college—my grandfather was an entrepreneur—and I always wanted to be an entrepreneur. So, I thought, let's do both.


I had the good fortune of landing in the Bob Orr Indiana Entrepreneurial Fellowship, which is an entrepreneurial fellowship for entrepreneurs right out of college, and then moved from there to be an early employee at ExactTarget, which was an email marketing platform that grew to be acquired by Salesforce. At ExactTarget, I found that there was a lot of opportunity to read and write a bunch of stuff. The CAN-SPAM Act, which was this giant piece of legislation, was just published. It monitored the email opt-in opt-out practices. I read and became the expert on that. I was the first deliverability consultant at ExactTarget. I would write lots of blogs and white papers; I wrote a chapter in a book; lots of case studies, and all sorts of content around the topic of email deliverability, and became one of the experts in email deliverability.

An English major is all about creativity, consuming large amounts of information, and then producing other stuff. It naturally fits into the tech world, where we're always trying to learn about new tech and new legislation, new things, and then consume it, and spit it back out in a way that people actually understand. That’s what I did in college and grad school. And that's what I do professionally. It's been an easier link than maybe others anticipate.

Karen Mangia

What I like about what you're saying is that we often underestimate how important it is for entrepreneurs to be excellent in reading, writing, and speaking. What are some of the other important skills you've discovered? Because your journey in entrepreneurship went beyond ExactTarget to other companies as well. What are some of those other critical and maybe underrated or less talked about skills that you see in successful entrepreneurs?

RJ Talyor

I left ExactTarget to work for a startup called Geofeedia, then I started my own company named Pattern89. Now, I'm involved in a lot of different startups in my current role.


Reading and writing are definitely big, big skills. I'll tell you, one of the things I see today is the importance of the ability to communicate ideas and pictures. If I was an expert in Figma, for example, that would be a really good skill. I'm not an expert in Figma, I tend to go to Google Slides or PowerPoint and draw with squares and circles and arrows and those types of things. Design thinking and the ability to communicate your ideas in a way that a designer or product person, or an engineer can then execute very quickly is a lot better than just being a white-boarder or saying out loud, “I want to do that.”


Being able to communicate in a language that others can execute on quickly is important. So Figma is a skill I've been working on, but I'm not an expert. I've seen a lot of other entrepreneurs really succeed when they know that very well.

Karen Mangia

Figma may be a new phrase for a lot of our readers. Educate us in a way that my soon-to-be 100-year-old grandfather could understand.

RJ Talyor

Well, imagine a canvas that you could create software with, and that anybody, even including your 100-year-old grandfather, could create what he envisioned software to be. It has lots of shapes and arrows and colors and everything. But it's built in a way that an average person could create what they wanted the thing to look like, and it looks pretty professional. Now, there are experts, designers, who can layer on top of that within Figma. It's a software program that's a free way to communicate your visual ideas into software and other things.

Karen Mangia

Practice Pictionary, that's what I heard you say. The basis of that game is someone's going to give you words, and someone has to draw those words. There is a give and take between what is spoken and heard versus what is visually represented. What I'm hearing you say is: in the process of creation, whether that's creating software or something else, the ability to turn words into images increases your effectiveness as a communicator.

RJ Talyor

It sure does. You have this idea. You've got to communicate what that idea is not only to create the thing, but to inspire the other people to come along and help you with it. Oftentimes, creating a pretty version of that idea is more inspirational than just speaking that idea. It also makes it more real. It also invites needed criticism. If you put something on paper that people can react to, and say, “I like this,” or, “I don't like this,” or, “I like this shape, or I like those colors,” or, “I don't understand.”


That is really, really important. Think about it. If you were to describe building a two-story red house, two people could draw a two story red house very differently. One might be brick, one clapboard. It might be modern in architecture or very classic. Getting something on paper helps us to then take it to the next step or criticize it or the idea until it becomes something real.

Karen Mangia

What you're pointing out as well is what a great tool to create more engagement to refine your idea. Some of us can hear words spoken and see a visual image in our minds. Others are better at interacting and engaging when they can physically interact and draw and see a picture.


You mentioned design thinking. Share more about how anyone who's thinking about entrepreneurship or intrapreneurship innovation could incorporate design thinking into what they're doing. What do you think are some of the most core skills or principles that anyone could apply?

RJ Talyor

Design thinking is a whole protocol that I am not an expert in. I want to say that because there are experts that can come and actually instruct you on how to apply it all. But when I think about design thinking, I think about how you go from an initial idea to the end result, getting over all the hurdles that are along the way. One of the things that I like to do when I'm thinking in that way is the whole trick of: How might we? How might we create a red house with two stories or something like that, inviting people into the exploratory process. Let's give away all the preconceptions about cost, sourcing, or location. The practicalities—let's push them off to the next conversation. Instead, let's imagine together.

One of the other things that I like to do in bringing ideas to life is writing. There's a lot of studies out there that say that writing is thinking, and that when you actually create something your brain will introduce new things, because you're actually putting it on paper either in words, or as you're creating something in a tool like Figma, or just drawing itself. You then create something new that you didn't know even existed—that whole creativity processes. I think it's really fun to put headphones on, play some ambient music, take those ideas, and try to create something with them without worrying about the what ifs or the practicalities that ultimately will have to be adjusted. But just think big and then come down from there.

Karen Mangia

What I like about what you're saying is that the question—“How might we?”—is a tool to move from constraints to choices. We are out taking walks or in some sort of a situation where an idea comes to us, and we tend to put ourselves in the constraints category because we criticize our idea. We think that's not a great idea, or no one else will think that's a great idea. What I like about that “how might we” is that it's a tool that says anyone can create anything. You just take that into a bigger and bigger space where you focus on the choices rather than on the constraints

RJ Talyor

Many entrepreneurs will do things like: “Hey, Karen, I want to tell you about this idea, but you need to sign an NDA or non-disclosure agreement first.” And I think that, unless you have invented something like the cure for cancer and are going to share with me the molecular formula of the injection or something, I don't think an NDA is needed because there are lots and lots of ideas. Ideas are cheap. It's the execution of the idea that's so important. And I think that sharing your idea visually or in text, or even in the conversation, and inviting that feedback, or even the criticism, as you're describing, is the way to advance ideas into something that's new. I'm going to create, even if we have the same idea; you would execute it based on your experiences, and I would execute it based on mine. It might be a totally different business we come up with.

Oftentimes we're scared to share a new idea because we don't want to look foolish or silly or unprofessional, or the idea is not fully baked yet. Some wonderful and amazing ideas and/or entrepreneurs decide not to start because they're nervous, and fear is a real thing. It's a real thing. Anyway, I like sharing ideas early and often and not getting bogged down in NDAs, etc. But instead, you know, finding trusted friends—the old Friend DA as I call it. So, you know, some kind of musings on that to help advance these ideas. They're really important.

Karen Mangia

What I heard you say is: ideas are not impact, and execution is monetization. You really can't monetize an idea until you start to execute, which is the moment at which that idea translates into something that creates monetary value and worth or leads to your ROI.

You mentioned something important there about fear holding even entrepreneurs back on their journey, and entrepreneurs are people who are already committed to press through the fear and step out into their own. Your role, RJ, at High Alpha Innovation is to coach founders and to support them on this journey. And what I'm curious about is, how do you create a safe space? And what can we all learn from you about how to create a safe space for those moments where people are stuck in that fear?

RJ Talyor

Three things come to mind. I love to use: what if. Let’s play what if? What if everybody loves this idea and you have too much business? What if COVID comes again, or whatever—just crazy scenarios. Let’s play those out a little bit.

The second thing that I like to do is to ask them to dream with me. My friend Tyler says that a lot—like dream with me, dream with me, let's go to a dream space. This is not real. Let's imagine. Both are the kind of entry points there.

And then, the third thing I like to do is rehearse. Let's rehearse a conversation with a prospect and let's play it out. Karen, you, and I are going to pretend; I'm going to try to sell this to you now. Or I'm going to try to pitch you on this idea. We're going to rehearse and so, you're going to have rehearsed all the objections; you're going to have heard some of the objections; you're going to get zinged in this conversation. But it's a safe space, because I'm your champion. I am your coach, I'm excited for you, and let's go for it.

So, we'll do rehearsals. And it's silly; it feels really weird, especially with a friend or somebody that you're working with to kind of go down that rehearsal path, but you find the objections, you find the criticism, those types of things and anticipate them. You won't anticipate all of them, but at least you'll be used to defending the idea outside of your head in a real space.

Karen Mangia

Rehearsal is a priority in any performance. Imagine if you showed up at your local theater, and the symphony or the play acting team got on stage and did that performance for the first time. How would you feel as someone who paid for a ticket? And yet, every day we walk into sales calls and pitch meetings with potential investors with very little rehearsal. What I like about what you're saying is the point of rehearsal is not to perfect and memorize a script, it is to prepare you to handle the unexpected nature of twists and turns and to be able to access that sage mindset that gets curious and ask more questions, as opposed to shutting down and withdrawing from the conversation into a panic.

RJ Talyor

I worked at Salesforce for a while, as you know, and I was a speaker on the World Tours. I had the good fortune of going to some cool places and speaking and I would do the marketing cloud demo. One of the things that they have you do as a prep for it is meet with a speaking coach. The speaking coach watches you while you’re giving a speech. They like the in the round format, where you're walking around. You are walking, wondering what to do with your hands while you're trying to coordinate a demo and that kind of stuff. It’s pretty overwhelming. They do have a script that they want you to follow, but the key point is, make it your own. You've got to make it your own, and you have to really own it; you can't just memorize and speak it back out.

The speaking coach was great, really direct with me, which was awesome. And I appreciate it. But one of the tips I've taken from him is that you need to rehearse anything five times out loud. And he said out loud because you're training your neural pathways. I'm not a brain expert, but I like to find different words to say the same thing.. but it's so tedious to have to do it out loud five times, especially if you're giving like a 20 minute talk. But I have used that trick over and over and over. I'll tell you, if I rehearse five times, and then go to bed, wake up in the morning and look at my notes. I can nail those presentations. I can nail those pitches. It's something I tell our team and we rehearse five times out loud. You can't say stop, stop, stop. Let's do it over again. You have to keep going. Like that's the trick.


I don't remember his name, but I appreciate that coach's advice, and I've used it.

Karen Mangia

What I've discovered about rehearsal is that it's an effective tool to calm your nerves. Most people get nervous, even if you're rehearsed and a practiced public speaker, that moment when you walk on stage and all of those eyes are looking at you, ready for this brilliant moment where you say something that informs or inspires them. I found it's easier to sit with those nerves when you know your content and that you're prepared. When you match, not rehearsing, not being prepared, with the nerves of the moment, you're just setting yourself up to struggle.

RJ Talyor

Exactly.

Karen Mangia

The businesses that you coach, span, every industry and every concept. What are some of the common denominators that you've discovered as a coach, both in swimming and as an entrepreneurial coach about mindset? What is the mindset we all need to embrace to step into peak performance?

RJ Talyor

Two things come to mind across both areas, which is adopting a can't fail mindset. That’s a hard thing to do because, in swimming, for example, if you sprint the first 100 of a 200, race, you're going to just give it all in that first 100, and the second 100, is going to be really painful, you can't quit—you can't give out at the 100. You'll get disqualified. Of course, in swimming you can do it, but it'd be embarrassing. I've actually seen some Olympians recently who have done that, and they just get blasted. There's other issues, like how do you give it your all on that first bit, but then know that the second half is going to be super painful, but then go through it.

It's the same with startups or with entrepreneurs because you have to go full speed knowing that the next week is just going to be painful. This is a silly example, but you might say: “I’ve got 10 contacts, I can reach out to those 10 contacts. But then what do I do after I've exhausted those 10 contacts from my potential deal?”

You have to believe that, when you've exhausted those 10 contacts, you'll have found other ways to get to new contacts, either by sourcing new contacts or having the contact introduce you to other people. There's a feeling of, “How do I keep some in the reserves, so that I can use them later?” We as humans want to do that. We want to anticipate that pain, and then plan for it. But if we plan for that pain, and we plan for a future pain, then we end up not giving our full selves as entrepreneurs and athletes. If you want to win, you've got to give your full self. There's a lot of self-care and mental health and all sorts of other things that go into that because you need to give your full self but also protect yourself.

I think that the winners are able to go kind of full blast and say, “Alright, I trust myself enough to be creative enough, that there will be more leads. There'll be more energy, there'll be something else that's coming up that I'm not quite sure of.”


That’s what the winning teams, the winning companies do as well as winning individuals, like in sports. From a mindset perspective, how do you kind of go from a mindset of scarcity to a mindset of fullness, feeling that there is more there. You may not be sure what that looks like, but trust that it will be there. That's a scary thing, trying to convince people and then just be super supportive and help them be creative through those challenges. That's the mindset I think that's most important.

Karen Mangia

An abundance mindset is an asset.


You're poking holes in a popular myth, that to be an entrepreneur, you must be exhausted all the time. If we turned on our favorite sport and the athletes, who we admire, got up to perform and looked like they could barely stand up, our immediate thought would be they're going to lose today. Yet we somehow celebrate this in the world of entrepreneurship.


What you're looking at are the routines, rituals, and boundaries that set entrepreneurs up for success. What is the balance that you've implemented yourself and that you coach others on as well?

RJ Talyor

I am not the poster child for this. I would just urge you to do as I say, not as I do. We talked a lot about swimming, I love swimming. Swimming is literally the only place in the world where the phone does not reach me. We talk a lot about mindfulness in our culture. From my perspective, mindfulness is nothing more than just getting in the pool and swimming for 45 minutes or an hour. I found that if I am in the pool three or four times a week, it's a reset. It erases lots of things. I can comfortably disconnect from a phone. Even when I go for a walk, I'll put something on my phone or I'll always be checking it. I feel really uncomfortable leaving my phone at home because of family. That's maybe my own issue.

But swimming, it feels really good to be just in the water physically, and then clearing your mind and exercising is always good. Whatever that space is for the entrepreneur, they also need to program that into their day. Entrepreneurship doesn't check in at eight o'clock and check out at five o'clock. It might be eight o'clock that you head to the gym, or eight o'clock, you drop the kids off, then your first meeting starts at 9:30. You know, that's an okay thing to do.

When I'm checking in with my people, I do a survey on a weekly basis, asking them four questions. Three of them are about their business. The fourth one is: How are you doing on a scale of one to 10? I try to understand those entrepreneurs and say, “What do you like to do? What keeps you going? Do you like to hike? Do you want to go out for dinner with your partner?”


It gets a little bit personal, almost a little weird sometimes, where I’m asking how they’re doing at work or if they went to yoga today—whatever the case is. It's not a professional conversation, but it's so important for the professional execution that they're doing those things that make them whole so that they can show up when they need to.

Karen Mangia

Now we all want to know, what are the three business questions you ask on this survey?

RJ Talyor

The first one is: What is the primary metric that you're pursuing right now? For some of the entrepreneurs, it's like users on the platform, sometimes it's sales, sometimes it's churn or renewal. But what’s that primary metric that you care about and that the whole business is positioned around?

The second one is: How are you performing against that primary metric? Are you performing above, at, or below your expectation? All of those answers are okay. It could be for the week, you're below. Now let's adjust. We need to improve.

The third question is: On a scale of one to 10, do you have product market fit? Product market fit is what we care about in software land. It is the art and the science of repeatability. A lot of these entrepreneurs need to sell maybe their first contract, then their second, and then their 10th. And we have to figure out a way to scale it—that's where product market fit comes in.


It's interesting to see what people say, why they think they have product market fit. It's such a squishy metric, I don't even know it's a metric...I try to measure it and ask them to put a number on it, so that we can see if it is increasing, improving or not, and then I've got enough data across enough entrepreneurs that I can understand. If we're at week 17, and you're at this low score, we've got to do some aggressive experimentation to get things back up, or if you're at this score, you're way ahead of where you should be, and we can work on other things like scaling your business. So, those are the other three.


Karen Mangia

When you ask the “how are you doing” question and you were reflecting on your own experience as an entrepreneur, what came to mind for me was the importance of giving yourself permission to create and commit to sacred space on your calendar for yourself, your wellness, your wellbeing. We would think it was odd if a high performance athlete told us they worked out 24 hours a day, seven days a week, and never rested. And yet, we take that on ourselves as entrepreneurs sometimes.

RJ Talyor

I definitely do that. I used to ask myself what my Board of Directors would think about what I'm doing right now. Would they be approving or disapproving? When I would take vacations or something like that—I've taken one vacation this year—what would they think about that? Or like I'm doing a podcast right now, what do they think about that? Is that a good use of the money that has been invested in this company? Sometimes the answer is yes, sometimes the answer's no, but it was a kind of a good way to judge how I was spending my time.

Karen Mangia

And your litmus test question is equally effective for people who have a personal board of directors. Imagine the people who are the key stakeholders in your life that you trust. The same question is powerful. What would my personal board of directors think about how I'm spending my time or treating myself right now?


Speaking of how we treat ourselves, something people say they miss sometimes about the office in this new world in which we live in and work, is the opportunity to gather around the watercooler for spontaneous conversation, which is why I have replicated a virtual water cooler segment on the show. Now here's how this works. I just have five quick and easy questions. You say the first thing that comes to mind, everybody gets to listen into our water cooler conversation. Are you ready?


RJ Talyor

Yes.


Karen Mangia

What time of day do you do your best creative work?

RJ Talyor

First thing in the morning, like 6AM.

Karen Mangia

Speaking of time, if you had one extra hour every day—the day now has 25 hours instead of 24. How are you going to spend your extra hour?

RJ Talyor

I would garden; I love gardening. So I would garden more, planting vegetables and herbs and stuff.

Karen Mangia

I love it. The gardening, the swimming. It's all the healthy habits. Maybe this leads into the next question. If you had to eat one meal every day for the rest of your life, what would it be?

RJ Talyor

I think tacos. Tacos just go so many different ways—just a classic taco.

Karen Mangia

Oh, imagine innovation applied to the taco all the time. I love it. The zombie apocalypse is coming. Who are the three people you want on your team?

RJ Talyor

That's not fair. I have four kids and my wife.

Karen Mangia

You're like, “I'm pleading the fifth on the zombie apocalypse. I can’t choose.”

RJ Talyor

I'd probably sneak all of them in there, but then I'd want somebody with some really good survival skills. Maybe Bear Grylls or something?

Karen Mangia

And last question: how can people stay connected with you and your thought leadership and what you're doing?

RJ Talyor

I'm pretty active on LinkedIn. Finding me on LinkedIn would be the right spot. The last name is Talyor, not to be mistaken with Taylor.

Karen Mangia

Well, thank you to RJ, Operating Partner at High Alpha, for joining us today on Success from Anywhere because…


Success is not a destination.

Success is not a location.

Success is available to anyone, anytime, anywhere.

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