155 - The Hardest Lessons I've Learned Building Businesses
In this episode of the MaYapinion® podcast, Maya Roffler shares some of the hardest lessons she’s learned while building businesses over the past 17 years.
From corporate America to entrepreneurship, from events and consulting to coaching, podcasting, and now building a tech company, Maya reflects on the business lessons that have shaped the way she thinks, leads, sells, and makes decisions as an entrepreneur.
This episode is a true MaYapinion® conversation.
Maya doesn’t just share surface-level advice—she breaks down the real lessons that came through trial and error, mistakes, pivots, relationships, burnout, revenue pressure, and learning how to build businesses in a way that actually supports the life she wants to live.
From realizing that clarity doesn’t come before action—but because of it—to learning that not every opportunity is actually the right opportunity, Maya walks through the mindset shifts and business truths that changed everything for her. She also shares why relationships have been one of the biggest drivers of opportunity in her businesses, why revenue is one of the clearest indicators of whether a business is truly working, and why saying yes to everything can quietly pull you further away from the kind of business you actually want to build.
This episode is especially valuable for entrepreneurs, founders, service providers, coaches, creatives, and women building businesses who are trying to figure out what really matters when growing something sustainable. Because building a business isn’t just about getting started. It’s about learning how to keep going, how to stay focused, how to trust yourself, and how to make decisions that align with the life you actually want to create.
What You'll Hear in This Episode
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Why Maya believes clarity comes from action—not from waiting until everything feels perfect
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The mindset shift that helped her stop holding herself back from launching, selling, and moving forward
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How perfectionism can delay growth and keep entrepreneurs stuck longer than necessary
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Why relationships have been one of the highest ROI investments across Maya’s businesses
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The role networking, referrals, and trust have played in building her event business, consulting work, and bereaved sibling community
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Why revenue matters more than likes, views, or follower count when it comes to validating a business
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Maya’s perspective on why sales solve problems in business
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Why not every opportunity is the right opportunity, even if it looks exciting or financially tempting
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What it means to build a business that fits your life instead of forcing your life to fit your business
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Why success isn’t just about revenue—it’s also about creating a business that supports the life you want to live
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Maya’s honest reflections on still learning, still growing, and continuing to evolve as an entrepreneur in real time
If you’ve ever felt stuck waiting for clarity, overwhelmed by too many options, tempted by opportunities that don’t actually fit, or unsure how to build a business that supports your real life—this episode will meet you there.
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[00:00:00] Welcome back to the MaYapinion podcast, where I share my unfiltered opinions about entrepreneurship with you and all the incredible women that listen to this show. I'm your host, Maya Raffler, and I am really excited about this episode. I'm gonna be sharing the hardest lessons I've learned while building businesses, and there's some good ones.
I'm excited about this episode. It's a good one. I've learned a whole lot. Over the past 17 years, I worked in corporate America, and I've shared that with you guys. I have built businesses. I am building businesses as you guys are listening and watching, and I'm sharing. And I'm sharing a lot on TikTok lately too, so if you're not following me on TikTok, I'm gonna plug that a little bit, because I want you guys to come over there and share.
And I'm actually sharing your challenges live on TikTok as well. That's a new thing that I've started to do. So come on over there [00:01:00] and drop your challenges and your business challenges, and I'll give you my opinion on what I think about those challenges. But today we're gonna talk about a couple of the hardest lessons I've learned while building businesses.
I have built podcasts. I have built an event business. I have built a consulting business. I have built... You know, I've done coaching as well, and now I'm building a tech business. And there's just so much, guys, that I wanna share with you and talk to you about. And so I'm just gonna jump into them. Like, what are the things that I've learned?
So this is probably my favorite one that I'm gonna talk about today, and it's clarity comes from action. What does that mean? Like, what does that mean? Well, I used to think that I had to have the perfect plan for everything. Like, if my course wasn't planned out perfectly, I wasn't ready to sell it. If I...
That's when I was doing, like, podcast courses and [00:02:00] building more of the coaching side of my business. I used to think if my website didn't look perfect, then I wasn't ready to bring on an event client. I used to think that if I didn't understand perfectly where I wanted my podcast to go, I couldn't start recording episodes.
And that is just such a myth, and it kind of goes back to my other episode the other day about, like, what I think is BS in business or BS business advice. But what I have found in my many years now of working in corporate America, now being an entrepreneur, in my opinion, the clarity that you're looking for truly comes from action.
The clarity you're looking for is on the other side of action. It's not from creating the perfect plan. And As a Virgo, as a mega planner, this was quite challenging for [00:03:00] me to wrap my head around that and to wrap my head around this whole concept that, oh my gosh, like, you know, everything doesn't have to be perfect before you start.
I really struggled with that, and I remember when I was kind of during the pandemic when I was working with a business coach, and I was working with some really incredible women. I was involved in some incredible, you know, women networking communities. I would say, "Okay, well, I don't know if I'm ready to open this course up yet because I haven't finished, uh, like what is the full transformation gonna look like for this person?"
And I remember getting advice that ... from a coach and also the community I was in at the time saying, "Maya, you do know what the transformation looks like. It's you. You're the transformation." And I thought to myself, that was clarity for me. I was like, wow. But the only way that I got transformation was by starting my podcast or starting my business and learning it.
I think that's something that really held me back, and I think I would have [00:04:00] really embarked on the entrepreneurial journey a lot earlier in life had I known that it doesn't all have to be perfect, and in the mess comes the clarity. So if you're holding yourself back from maybe another business venture or starting your business venture or moving to the next point in your business because you're not, you don't feel like you're ready, you're never gonna feel like you're ready.
Movement forward, even just a little step every day, those actions that you do, that's what's gonna bring you clarity for your next business, your next step, your next move, your next level up. It's action. That's my opinion on that, but action brings the clarity. Clarity does not make you take action. So the next thing that I would say is relationships matter more than you think Most of the opportunities that I got in the beginning were from people that I know, and [00:05:00] still to this day, it is from networking and knowing certain people in these communities and in these environments.
Most of my clients come from people, people who know me and trust me and have worked for, with me. And most partnerships come from people. So as I've started to partner, this is more for my Surviving Siblings brand where I help bereaved siblings, but these strategic partnerships with other influencers and other people that are well-known in the bereaved community, it's, it's those partnerships come from us trusting each other and trusting other people in the community and realizing we can collaborate together.
So more opportunities come from that. Relationships have truly built most of my businesses, but I would say the strongest relationship-built business is my event business as well as my bereaved sibling community that I do. That's more of a not-for-profit business that I do. But I would say all of my, um, clients that came along in the beginning when I first [00:06:00] launched my event business, I started consulting in 2017 and then went all in in 2020, and my first few retainer clients were people I had done, uh, some gig work with in the past, other people referred me because we had worked together, marketing agencies referred me, I got referred because of my corporate work that we had done together.
So those are things that, that have made it possible for me to be a business owner and to be an entrepreneur. So do not underestimate the power of relationships and who's going to think of you and who's going to keep you top of mind. It's life-changing. So my opinion and, and takeaway for this, relationships are one of the highest ROI investments that you can make.
It's huge. It's huge. Don't underestimate them. In my opinion, it's what can actually start your business is just one good relationship. You could walk out today and meet [00:07:00] someone at a networking event, meet somebody through a trusted partner, meet somebody who refers you, w- wherever that is, maybe someone from your past life comes back up again.
You have drinks with them or coffee with them, and they start talking about an opportunity. Those have been the biggest opportunities. Do not estimate, underestimate them because relationships, a- again, in my opinion, are one of the harrest, highest ROI investments that you can make. It is truly just so powerful, and it's how I've built so much of my business.
It's incredible. Um, so don't underestimate that. Another thing, this is one that's not so fun to talk about, but revenue solves problems Sales solves problems in every business, and people don't always wanna admit that, but it does, right? So something to think about regardless of what type of business you're, you're building.
People see, you know, businesses online, they're like, "Wow, they have so many followers," or, you know, [00:08:00] followers don't pay bills. Mm-mm. People complimenting you, think you're great, doesn't pay the bills You know, people like what you're doing, they like your content, or they like your idea for your business, or they, they know you're a hard worker.
What- that's all great, but that doesn't pay the bills. Revenue validates your ideas. Revenue creates options for you, and revenue, money coming in, validates the fact that your business is working and validates that there's a, a r- reason that you're selling your product, service, whatever it is that you're doing.
Doesn't matter how many likes you have. It doesn't matter how many views you have. And I think that is a lot of smoke and mirrors that I ran into early in my business because I started to get a lot of followers just because of my public, like, public things that I was doing at the time, and I used...
Actually, I have less followers now [00:09:00] than I did, um, at least for m- for my opinion. Um, and I used to think, "Oh my God, that means I'm gonna have less revenue coming in and less..." I had this, all these misconceptions about it. The reality is followers, likes, views, they don't always equal revenue because you have to be able to convert, and you have t- uh, how do you know if you're in front of the right people if it's not validating your business ideas and your actual, like, they're not buying from you?
So who cares how many people are watching your s- I, at least I don't care. In my opinion, it doesn't matter how many people are following you. It doesn't matter how many people are watching your stuff. I would rather 10 people watch something and it's for them, and they're invested in whatever I'm offering versus 100,000 people watching and maybe one person is like, "Okay, maybe," or zero people.
Who cares? Who cares? I'm not, I'm not out here to be an influencer. I'm out here to create products and services, fill in the blank for you, that help [00:10:00] people solve a problem. So in my opinion, a business isn't validated when people just like it and they think it's cool. Who cares? Who cares what they think?
It's validated when people pay for it. Just remember, like to add onto this too, in my opinion, remember, sales solves everything in business. Everything. As long as you have sales coming in, you've got a business, and you can rock and roll. Doesn't matter if people like, like it. Doesn't matter if people think it's cool.
In my opinion, that does not matter at all. It matters are people willing to pay for it, and are they paying for it? And don't ask people. This is another mistake we make all the time. Huge, huge business lesson here. Don't ask people, "Do you like this enough to pay for it?" People are often going to tell you yes.
"Oh yeah, it's great. It's great. Of course I would pay for it. Of course." Will they pay for it? Watch their behavior. Actions speak louder than words Cool. That's great. They say they'll [00:11:00] pay for it. No You gotta test it. You gotta see if they really will. All right, here's my next lesson that I learned. Not every opportunity is the right opportunity.
This, I, I learned this lesson really early on, and sometimes I still have to remind myself about this one, but not every opportunity is the right opportunity, in my opinion. When you are early in your business, though, it can feel like, "Oh my God, I'm not gonna get another client again," or, "I'm not gonna get another opportunity again, so I have to take this," like, "I have to do this."
And when you get in that mode of, "I have to take this," or, "I have to do this," you start to do a couple different things. Like you're saying yes too often, which will drain you and create burnout, and you're saying yes to things that aren't necessarily aligned with you or your business model. Remember that every opportunity has a cost too.
So maybe you're taking a client just because you [00:12:00] really feel like you need the revenue, but maybe they're not aligned with you. Maybe they're a difficult client. Maybe they're not paying as much as you're really... Like, your work is worth it, right? Maybe you're taking on a 10, $20,000 client and only for 2,500, five grand.
It seems like a good idea at the time. It's like shiny object syndrome, but in reality, it might not be a great idea 'cause you're gonna be resentful towards that. So keeping focused helps create momentum. I realize that, and even though sometimes it would scare me a little bit when I started to say no to the shiny objects that would come up, I realized it was just a distraction.
Those shiny objects are just a distraction. I realized that I had to stay focused and only with clients that align for me, and I still have these things come up. I... Just over the weekend, I had a client that I've done corporate [00:13:00] events for, different things for. Great client, great guy. Um, reached out, asked me if I wanted to, you know, do a birthday party.
We don't do birthday parties. We don't do personal parties. We don't do things like that. I don't do weddings. I don't do anything like that. My event company is hyper-focused. We only do corporate, go- government, and nonprofit engagements. That is it. And we have a certain amount. We don't go over. We don't exceed a certain amount of attendees.
We have a s- minimum budget, and I stick to that now. Had I gotten that text from that client a few years ago, what do you think I would've said? "Sure, sure." It was a shiny object. It's not aligned with what I do. We don't do personal occasion events. So that's a great example. So just remember, this is my opinion on this one, every yes is a no to something else.
So the second you start saying no to things that are not aligned for you, whether it's financial, whether it's just [00:14:00] personal brand- Whether it's what you really excel at, w- it- wherever it falls, sometimes it's not just about money. Sometimes it's about the brand alignment. Like this particular opportunity this weekend for me, it's not, it's not our brand.
It's not what we do. It's not in alignment with that. So you don't have to say yes to everything. In my opinion, every yes is a no to something else. Remember that. And so you want to remember because when you are saying yes to something that's not aligned, you're saying no to something that could be super aligned.
Just my opinion on that This one is interesting, and I think I'm still learning this myself, and so we'll continue to learn this together. But I- I'm- I'm really happy where things have gone for me personally, and I hope you can do this for yourself. Build a business that fits your life. Build something that fits your life.[00:15:00]
Success is not just about how much you're making, although we- I- we all wanna be successful and be able to provide the lifestyle that we want for ourselves and our family and, you know, our loved ones. But you have to really love what you're doing because there's gonna be days that you don't like some of the things that you have to do.
Think about your lifestyle and, and how you run it. If you have kids and they're in school during the day, like, that's when you should really be chunking out a lot of your work. Um, if you're like me and you're a night owl, I like that flexibility where I don't have to get up every morning at, like, 5:00, 6:00 AM.
It's just not me. That's personal for me. I'm not waking up at 5:00, 6:00 AM unless I've got an event to go to, and then I'm energized and I wanna do it anyway. So that's a personal lifestyle thing for me. Think about, you know, your energy and your bandwidth. Like, how much do you really have to give to your business?
What's a realistic goal financially for you, and how much output you really have? And think about what you actually want. Like, why are you doing this? And those are [00:16:00] conversations I had to have with myself a whole lot. For me, I wanted to build a business that fits my lifestyle, where I work, I work in sprints, and I have, like, really productive days, and then some days I'm like, "Eh, I'm doing emails.
I'm doing what I can." So I'm a sprinter i- within the marathon because running a business is a marathon. But I'm also a sprinter where I like to, like, take these, like, stretches of, like, "Oh my God, I can have these 12, 14, 16-hour days and just really, really work." And then I'm, like, a little laid back. And I'll go through those.
And so those were deep things I really had to ask myself. Like, how do I work most effectively? How do I dial in the best? I also know that I have to work from home. I love working from home. I don't wanna go in- into an office every day. So this can... I mean, this could be a whole episode. Like, how do we build a business that fits your life?
And if you guys give me enough feedback, I'll do a whole episode on this. But think about it this way. This is my opinion and takeaway from [00:17:00] this particular step. Build a business that supports your life. Build a business that supports your life, not a life that supports your business. Because if you wanted a life that supports your business, you just go, like, back to corporate
That doesn't make any sense. So you wanna build, you want the business to support the lifestyle that you want, in my opinion. You don't want your life to be revolving around your business. And that's a tough one for entrepreneurs, and it's a tough one for me, in my opinion, because my life really does revolve around my business.
But the reality is my business is really supporting my life because I love what I'm doing. So this one is, is one that I'm working on with you guys, but it really drives home for me, and I think it's a really positive thing for all of us to think about and really dial into as we're thinking about how we [00:18:00] wanna craft our lives, and how we wanna excel in life, and how we want our business and, and what we enjoy doing to support our life.
And to be... Th- they work more harmoniously when you think of it like that. And when you think of it the other way, like your life is supporting your work, that's not, you're not really living. And that's something I actively work on, uh, in full transparency with you guys, o- on a, on a daily basis because I'm a little bit of a workaholic.
I love it. I mean, come on. I run two podcasts. I help women with my opinion. I've done the coaching. I'd love to work with you if that's something you would wanna do. We'll talk about the audit in just a second. I have an event business. I love my event business, and now I have found a co-host as well.
I'm a busy gal. I'm a busy gal, but I'm really dialed into these things that I do, and I love it. So these are things that took me, you know, 17 years to learn, and I'm still growing [00:19:00] with you, but I really strongly believe in my opinions about this and my perspectives on this. I'm still learning every day with you, like I mentioned, and I enjoy it.
I enjoy showing and being really vulnerable about where I'm at, as well as sharing my opinions on where I've been and where I think you should go, and what I think works and what I don't think works. And not everybody's gonna agree with my opinion, but that's why it's my opinion. So this is our last episode until we come back in late summer, early fall.
And I thank you guys so much for listening to our relaunch coming back. We- don't forget, we're doing submit your biggest business challenge. So if you want me to read your business challenge on TikTok, you want me to read it on future episodes when we come back for our late summer, fall launch, for my opinion, drop it in.
There's a link in the show notes for you to drop your feedback in. It could be [00:20:00] anonymous. You can leave your name. It's up to you, and I will answer it. Really excited to be doing this and sharing it on episodes, but I'll also be sharing them on TikTok in little, little blurbs. So if you're not following me on TikTok, it's @mayaraffler.
I will continue to share my challenges with you guys, and share all of the things that I'm going through as I'm building a new business, my Find a Co-Host business, as I continue to grow my event business, and of course, continue this incredible podcast with all of you listening. And I really have enjoyed bringing this back, and having women on the show sharing their challenges.
I can't wait to hear from you about your challenges, and continue to share my opinions on future episodes. So we'll see you back when we relaunch the next couple episodes of the show. Until then, I hope you guys enjoyed my opinions, and we'll see you on social media [00:21:00]