The B2B Podcast Index
Index
All categories
MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
MethodologySubmit
Best of:MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
An independent project byFame
SearchBest episodesGuestsInsightsMethodologySubmit a podcast
Index/Leadership/Creating Confidence with Heather Monahan
Creating Confidence with Heather Monahan artwork

Confidence Classic: Start Before You Feel Ready, With Heather!

Creating Confidence with Heather Monahan · 2026-07-01 · 32 min

0:00--:--

Key moments - from our scoring

Substance score

26 / 100

Five dimensions, 20 points each

Insight Density8 / 20
Originality4 / 20
Guest Caliber3 / 20
Specificity & Evidence9 / 20
Conversational Craft2 / 20

This episode centers on Heather Monahan's core philosophy: done beats perfect, and waiting is the enemy of progress. She breaks down how to start a podcast, business, or career pivot - emphasizing that the framework is identical across all three, though execution details differ. Monahan shares two detailed case studies of landing major guests. Her Gary Vaynerchuk story showcases tactical persistence: she DM'd him for years, set up Google Alerts on his name, found his wine-company partner, offered value first (sharing her Gala Winery campaign experience), and leveraged that relationship to get Gary as her podcast's first guest - then used that interview to pitch herself onto his show. Her Sara Blakely story demonstrates relationship-driven opportunism: through friend Scott McGregor's connections to Jesse Itzler, she built goodwill by solving problems for Jesse's business partner, made introductions of her own, and when Jesse's internet failed mid-Zoom, immediately offered to fly to Atlanta - turning a technical mishap into an in-person interview that led to a stage appearance interviewing both at a sales conference. Throughout, she emphasizes the Perry Ellis clothing-line failure as proof that 'no' often means 'not now,' and that building relationships and staying flexible often reveals the right path forward.

Key takeaways

  • →Take messy action now rather than waiting for perfect timing - done is always better than perfect, and waiting delays progress by months or years.
  • →Lead with value creation: before asking for anything, identify how you can help your target, whether a potential guest, partner, or contact, and solve their problem first.
  • →Persistence combined with strategy works: use tools like Google Alerts, LinkedIn, and relationship mapping to find alternative entry points to hard-to-reach people.
  • →In-person meetings create exponentially more opportunity than virtual ones, and showing willingness to inconvenience yourself (flying to Atlanta last-minute) signals genuine commitment.
  • →Leverage your smaller size and flexibility as an advantage: unlike massive corporations, agile entrepreneurs can pivot fast, change direction, and capitalize on serendipitous opportunities.

Topics in this episode

LinkedInAnalysis paralysisSara BlakelyGary VaynerchukQVCGoogle AlertsJesse ItzlerPerry Ellis InternationalHSNGala Winery

Questions this episode answers

How do you get high-profile guests like Gary Vaynerchuk or Sara Blakely on a new podcast?

Use Google Alerts to monitor your target's activities, identify secondary contacts (like their business partners), add value to those contacts first by solving problems or sharing expertise, build genuine relationships, and show willingness to be flexible and inconvenience yourself - both Gary and Sara came through persistence, relationship-building, and demonstrating value rather than direct asks.

What should you do if a potential partner or guest says no?

Treat 'no' as 'not now' rather than final rejection, continue building relationships, stay open to alternative paths, and keep moving forward with other opportunities - Heather's Perry Ellis partnership didn't close, but the relationships and knowledge she built led to connections with QVC and HSN that may yet bear fruit.

Should you wait for the perfect conditions before starting a podcast or business?

No - waiting is analysis paralysis and wastes time; instead, start now with imperfect information, take messy action, move fast, break things if needed, and let failures and setbacks guide you toward where you're actually supposed to go.

How do you stand out when reaching out to busy, high-profile people?

Build a credible online presence (LinkedIn profile with recommendations, content that shows your real persona), lead with a specific value offer rather than a favor-ask, make the ask easy and low-friction, and show genuine interest in helping them solve a problem before pitching yourself.

What was the turning point in getting Sara Blakely on Heather's podcast?

Scott McGregor, a close friend, introduced her to Jesse Itzler's business partner; Heather added value to that partner, and when Jesse's internet failed during a Zoom call, her immediate offer to fly to Atlanta in-person impressed him enough to say 'yes' and later lead to a stage appearance interviewing both Sara and Jesse at a sales conference.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

8 / 20

The episode contains a handful of genuinely actionable networking tactics (Google Alert on targets, approaching adjacent contacts, leading with value before the ask, asking for the close in the moment) but these are buried under a heavy load of motivational platitudes and throat-clearing. The ratio of insight to filler is poor for a 32-minute runtime.

I took out a Google Alert on Gary Vaynerchuk's name. Now, if you have a target or someone you're going after that you want to have as a business partner or want to pitch for an idea, take a Google Alert out on that person.
I saw he wasn't as well known as Gary Vaynerchuk, so I figured he'll be easier to get to.

Originality

4 / 20

The episode is almost entirely recycled motivational content - 'done is better than perfect,' 'move fast and break things,' 'you can't connect the dots looking forward' (a Steve Jobs line), and 'analysis paralysis' appear verbatim. The personal anecdotes are original in their detail but the lessons extracted from them are thoroughly generic.

Done will always be better than perfect. Move fast and break things.
You can't connect the dots looking forward. You can only do it looking back.

Guest Caliber

3 / 20

This is a solo episode with no guest whatsoever. The host, while a former CRO with real corporate experience, is now primarily a motivational podcast personality and speaker, which limits the practitioner depth. There is no external expert to evaluate.

Hi and welcome back. I'm so glad you're back here with me this week. Okay, so when I'm asked a question a multitude of times, I take that as a sign I should share the feedback the answer with you on the podcast.

Specificity & Evidence

9 / 20

The episode earns points for naming real companies (Perry Ellis International, HSN, QVC), real people (Gary Vaynerchuk, Sara Blakely, Jesse Itzler, Ryan Serhant), concrete timelines (nine months on the clothing line, two years of DMing GaryVee), and a step-by-step sequencing of events. However there are zero hard business metrics, no revenue figures, and no data to validate any outcomes.

For months, uh, about nine months, we worked on the line, we worked on the messaging, we worked on some really unique structures, strategies, and we were ready to go to market.
I started DMing Gary Vaynerchuk, and I actually DM'd him for a couple of years before he ever got a response.

Conversational Craft

2 / 20

This is a solo monologue with no guest, no questions, no follow-ups, and no productive friction of any kind. The host never challenges her own assumptions or steelmans an alternative view, and there is no conversational structure to evaluate beyond storytelling pacing.

So recently I've received so many DMs asking me how to start a podcast, how to land big guests. How did you get Gary Vaynerchuk? How did you get Sara Blakely? So I, uh, keep getting these questions.

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker B76%
  • Speaker A24%

Most-used words

show25first20start17podcast17value17confidence16help16wealthfront15creatine15back15gary15keep15different15perfect13vaynerchuk13partner13

Episode notes

Are you waiting until you feel more ready before taking the next step? In this episode, I share why waiting for perfect timing could be the very thing holding you back from the opportunities you've been hoping for. I break down the mindset that helped me stop overthinking, embrace imperfect action, and trust that clarity comes through action. I also share the stories of how I landed guests like Gary Vaynerchuk and Sara Blakely, why leading with value has opened doors I never could have forced, and how setbacks that once felt like failures ultimately became stepping stones to something even bigger. Get ready to stop waiting for the perfect moment and start creating the future you want today. In This Episode, You Will Learn: Why waiting for perfect timing is keeping you stuck. What a failed Perry Ellis partnership taught me about taking risks. The networking strategy that helped me

Full transcript

32 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: If your revenues are at least in the seven figure, go to NetSuite AI/Monahan. Built for the every industry, ready for every boardroom. Netsuite AI/Monahan. M M O N A H A n netsuite Next. Join over a million people already building wealth with confidence. Head to wealthfront.com confidence to get started. Terms and conditions apply. If you want to try momentous signature Spec Creatine, head to livemomentous.com and use code CONFIDENCE for up to 35% off your entire first order. Livemomentous.com promo code CONFIDENCE. Over 30 million customers have trusted Zazzle with their most important moments. Right now, save 25% on your first order@zazzle.com that's 25% savings on your first order@zazzleen.com Go make something zamazing Zazzle.

Speaker B: That's how do you start a podcast or how do you start a business, or how do you make a career change? Here's the reality, and this is what the majority of people struggle with. Just do it. Waiting is not the answer. Done will always be better than perfect. Take messy action. I've just seen so many people wait so long. It's that analysis of paralysis, right? You just, you want it to be the perfect time, the perfect conditions. Oh, the marketplace isn't right. All of that is BS excuses. No matter what it is that you're thinking about in your life, the answer is start now. Come on this journey with me each week when you join me, we are going to chase down our goals, overcome adversity, and set you up for a better tomorrow. Fasten your seatbelt. I'm ready for my close up.

Speaker A: Tell me, have you been enjoying these new bonus Confidence classics episodes we've been dropping on you every week? We've literally hundreds of episodes for you to listen to. So these bonuses are, are a great way to help you find the ones you may have already missed. I hope you love this one as

Speaker B: much as I do. Hi and welcome back. I'm so glad you're back here with me this week. Okay, so when I'm asked a question a multitude of times, I take that as a sign I should share the feedback the answer with you on the podcast. So recently I've received so many DMs asking me how to start a podcast, how to land big guests. How did you get Gary Vaynerchuk? How did you get Sara Blakely? So I, uh, keep getting these questions. First and foremost, this is sort of interesting. I don't really think of it like how do you start a podcast, or how do you start a business, or how do you make a career change? All those things are essentially the same, right? I mean, there can be some nuances in regards to when you launch a podcast. Should you just do solo episodes, AKA what we're doing right now, or what category do you want to be in an Apple podcast? Right? There are some nuances that are unique. It's same thing with starting your own business. What product or service are you going to sell? What problem do you solve? There are unique questions you're going to ask around it. But here's the reality, and this is what the majority of people struggle with. Just do it. Waiting is not the answer. Done. Wait will always be better than perfect. Take messy action. And I've just seen so many people wait so long. It's that analysis of paralysis, right? You just, uh, you want it to be the perfect time, the perfect conditions. Oh, the marketplace isn't right. All of that is BS excuses. And I get it. Listen, for over a decade, I was not happy. Not living my best life, not living up to my potential in a job. But I was afraid to leave. I was afraid to pull the trigger. I couldn't see what was on the other side of that gap, right? If I'm gonna leap, well, what's out there? I had no idea. And, uh, because I couldn't see it with clarity, I thought I couldn't go. I was wrong. I think all the time now, if I had left corporate America and that job where I was not treated well, I wasn't respected, and I allowed it to go on, if I had taken that leap that I took five years ago, now, could you imagine if I had taken that five years earlier? I'd be light years ahead. I can't even imagine. So no matter what it is that you're thinking about in your life, if you're always questioning if you should leave the relationship, if you're questioning if you should leave the job, if you're questioning if you should invest in yourself, start the podcast, start the business, whatever it may be. The answer is start now. There's never gonna be a perfect time. Take the messy action and go for it. Here's a quick story. When I first got fired, one of the things I wanted to do was partner with a massive brand to give me that brand cachet that I felt like I had lost because I no longer had a massive company behind me anymore, Right? Which also. That's just all ego and bs. But it's what I needed at the time. So anyhow, I ended up partnering with Perry Ellis International, which is a multibillion dollar clothing brand. And I felt like this is exactly the kind of partnership that I want that's gonna give me that swag and presence. And, you know, the PR teams were announcing it everywhere, and it made me feel really happy. I felt like, okay, I'm back. That was fast. All right, way to go, Heather. However, to the point, done is always better than perfect. I pitched Perry Ellis on this clothing line that I wanted to launch together in partnership with them because they already have the clothing factory set up. I didn't. I knew what I wanted the messaging to be, the marketing. I knew that I wanted to sell it on tv, on hsn. I mean, I had so much of this business plan mapped out, and I was ready to hit the ground running, but I needed someone who could actually manufacture the clothes, and I wanted to bring great quality products to market. Okay. So they needed some new revenue streams. It seemed like a great partnership. For months, uh, about nine months, we worked on the line, we worked on the messaging, we worked on some really unique structures, strategies, and we were ready to go to market. I went to hsn. I got us the meeting. Bottom line is this. We did not get the deal. And that was a really difficult no to take because we had worked so long on the product line. Nine months when I had just lost my job. Right. So I needed revenue. And I was so fixated on this idea hasn't come to fruition yet. Um, or didn't come to fruition the way that I thought it would. Right. No. Can also be not right now. So what I learned from that situation, why I'm glad I still just jumped in and did it, is I learned so much about hsn. I learned so much about QVC selling products and services online. I made so many contacts at qvc, at, ah, hsn. Right. And basically, here's where it led me. Again, it hasn't come to fruition yet. Listen, I believe the best is yet to come. It's God's plan, not mine. Right. I have these ideas, I have these senses in regards to, ooh, this is a great concept. Marketplace is ripe for it. I love that it solves a problem. It's within my community. Right. Like, I get a feel for. Okay, this could be amazing. It's right in line with my brand and what I live and believe. And I get excited about things. I go for them. They don't always come to fruition or happen or they haven't yet. And it's about keeping your mind open to that possibility. So to that end, I am, um, continuing to work on different products and services. I still have that vision. For me, I've made such great contacts that I know I could tap at any point in time. And they've taught me. The key that I was missing when I was with Perry Ellis is their products were too similar to stuff that they already had on the air. It wasn't unique enough, it wasn't special enough, it wasn't different enough. And so Perry Ellis didn't want to change who they were. Right. They're a multi billion dollar company. That's cool. I get it. But. But I'm a smaller company. I can change and pivot fast. Right. So take advantage of what's unique and different about you. Perry Ellis is a massive company. They can't pivot quickly. I'm a smaller company. I can pivot really fast. Think in your mind. Yeah, you might not be the multibillion dollar Goliath in your industry, but what's unique and different about you that you can leverage to get yourself ahead. The key is, in my opinion, done will always be better than perfect. Move fast and break things. You'll fail. Figure out solutions along the way that will direct you to where you're really supposed to be going. Maybe Perry Ellis wasn't my partner. Maybe somebody else is. And maybe these new relationships that I've been forming along the way are gonna reveal who that right partner is. And when the timing's right, watch out. You know, you can't connect the dots looking forward. You can only do it looking back. And you've got to have faith and belief in yourself. Okay? Done will always be better than perfect. Move fast and break things. Okay, so I want to get back to these questions I kept getting asked. And I'll start with the Gary Vaynerchuk story, if you haven't heard it before. So people ask me, how did you land Gary Vaynerchuk for a guest? That's incredible. Yeah, it was incredible. Number one, I got really clear on my intention. I knew I was going to do it, and I did not know how. Story of my life, right? But I had faith and commitment. I was getting him as my first guest on the show, so. So you need to get really clear. What is your intention? Get clarity around the goal, write it down, and hold yourself accountable. I started DMing Gary Vaynerchuk, and I actually DM'd him for a couple of years before he ever got a response. Back then, I got a Response back and got blown off. That's fine. Part of sales, right? Sales is a numbers game. So I knew I had to keep pursuing and take a different angle or pursuit. That's when I took out a Google Alert on Gary Vaynerchuk's name. Now, if you have a target or someone you're going after that you want to have as a business partner or want to pitch for an idea, take a Google Alert out on that person. It is brilliant. Every morning when you wake up, you're going to have in your inbox what's going on in their life. And so within a couple of weeks, I saw an announcement that Gary Vaynerchuk was launching a wine company with a partner. And so I jumped on that partner's name. I saw he wasn't as well known as Gary Vaynerchuk, so I figured he'll be easier to get to. Then the next thing I did is I said, how can I add value to this person? Right? When we show up wanting to serve other people, people are gonna be more open to taking our calls, to wanting to hear from us, to wanting to be helped. So I sent a DM to his partner on LinkedIn. And, uh, on LinkedIn, I have a presence, right? I've been showing up there for years. You can tell I'm a real person. And if you look at my page, you can see the reviews of my work, get reviews and recommendations of your work, and create content that showcases who you really are, you know, not a fake Persona. So that people say, oh, yeah, that's the kind of person I'd want to take a call from. Right? So you got to do the work, invest in yourself, show up on these platforms. And I shot this guy a note. I said, hey, I saw that you are partnering with Gary Vaynerchuk to launch a wine brand. Just wanted to let you know I've had tremendous success in business and in marketing and media for the last two decades. But prior to that, I was actually in the wine business and launched a massive campaign for Gala Winery and learned what to do and what not to do with an alcohol launch. If you want to hear some of my hacks so that you don't have to make the mistakes I made, I'd be happy to jump on a quick call and share them with you. Add value. How can I help this person solve a problem or gain information they may need. He responded right away. Oh, my gosh, I would love to. Thank you. Um, what day works this week? We jumped on a call. We were on a call for over an hour. And at the end, I was sharing with him everything that I had done wrong, everything that I had learned and trying to give him a step up or a boost of help. And in the end, the last thing he said to me was, thank you so much. How can I ever repay you? If there's ever anything I can do for you, don't hesitate to ask. Consider it done. And I said, oh, my gosh, it's so funny you say that, but I'm launching my podcast and I really want to have Gary Vaynerchuk, your partner, as my first guest. Can you make that happen? And he started laughing, and then he did. So you never know. I didn't know that he would offer that to me. Right. But I just know that I'm going to be nowhere if I do nothing. I'd rather, rather go out, put my best foot forward, and find ways to help people solve their problems, help add value to them, and then, uh, start building a relationship from there. You never know how quickly that could turn into something, an open door to exactly what it is that you're trying to accomplish. Which, you know, for me was to get to Gary. And then when I was at the end of my interview on my show with Gary Vaynerchuk, I asked, hey, Gary, do you think that you would want to have me as a guest on your show? I believe I can add value to your audience by A, B, C and D. I on the spot, showed up and talked about how I could add value to his audience. And I went for the close, and he said yes. And inevitably, he had me on his show too. So you've gotta be willing to take those risks. You gotta be willing to show up. You've gotta do the work right, establish your brand, create the content, get the reviews and recommendations, show who you are, showcase your brand, your Persona, and allow people to get to know you before they actually meet you. And that can invite opportunity in as well. Okay. That is how I landed Gary Vaynerchuk, which I'm, um, super grateful. He was my first guest. Go big or go home. If you wanna laugh, go back and listen to that episode. It was in 2019. I definitely was nervous. We'll just leave it at that. Of course I was nervous, but done will always be better than perfect. I'm so glad I did it. I'm so glad he was my first guest and super proud of that. Meet a different guest each week.

Speaker A: If you had been around this house the last couple of months, you would know. Total chaos. My son had graduation, a 19th birthday party, going away for the summer. There was a lot going on. And if you've ever been the person planning the events, I'm talking the invites, the save the dates, the favors, the thank you cards. All of it. You know it gets out of hand fast. Zazzle is how you pull it off without losing your mind. One place, one style. Fully customized. From the first invite your guests get in the mail to the last card they leave with, Zazzle covers the full event invitations, save the dates, place cards, programs, signature party favors, thank you notes. All customizable to match your colors, your fonts and your vibe. Order one or order 500. Whether it's an intimate dinner or 200 person reception, zazzle scales with you three steps. Pick a product. Find or build a design. Add your details.

Speaker B: That's it.

Speaker A: Zazzle handles the rest. Over 30 million customers have trusted Zazzle with their most important moments. Mine has been unbelievable because I am not the person who is a designer. I am not the person who even remembers to do the thank you card. I need Zazzle. And Zazzle made it so easy for

Speaker B: me to get through the last couple

Speaker A: of months of events with my son. And I am so grateful we did and we pulled it off with style. Right now. Save 25% on your first order@zazzle.com that's 25% savings on your first order@zazzleen.com Go make something zamazing zazzle.com they say that every day your business is late to AI, you fall two days behind.

Speaker B: But how do you keep up?

Speaker A: The competition is only moving faster. Fortunately, there's NetSuite next. You probably know NetSuite, the AI powered business management suite that securely connects all of your data. It's a unified suite that brings your financials, inventory, commerce, HR and CRM into a single source of of truth. Trusted by over 43,000 customers, NetSuite Next is the next huge leap in how business gets done. Because AI is built into everything you do, it automatically surfaces insights throughout your day. AI agents work alongside you to solve problems and handle routine work. And anytime you have a question about anything, ask just like you're having a conversation with a colleague. NetSuite is customized for a wide range of industries, so it supports the way your business truly works. If I had needed this product, this is exactly what I would have used. For the first time ever, you can try netsuite Next for free. If your revenues are at least in the seven figure, go to netsuite, AI Monahan. Built for the every industry ready for every boardroom. Netsuite AI Monahan M M O N A H A N netsuite Next.

Speaker B: Confidence Clear.

Speaker A: I ask you to try to find your passion.

Speaker B: People ask me a lot. How did I get Sara Blakely on the show? She is really hard to get, Right. Both Sara Blakely and Gary Vaynerchuk Charge 6/plus figures to do speeches anywhere. I mean, they're just. They're really hard to get to. And interestingly enough, Sara Blakely is a very different story. So I have a very great friend, Scott McGregor, who, if you're listening, shout out to you. Uh, ride or die. Incredible person who has helped me so much. I try to repay him in any. In every way I can. Cause he's just an incredible person doing great work, does so much work for charity. Just a wonderful person. Just, uh, he's a give back guy. My kind of people. Okay, so anytime you're giving back, you know, again, you're creating that flow of other good people to come to you and more good things to happen. So, leading with positivity, leading with giving to others. Anyhow, Scott and I got to know each other when he was creating a book for charity. I wrote a chapter for him. I was supporting him, he was supporting me. We became really good friends. At some point, when he heard I was launching my podcast, he said, well, give me a list of ideal podcast guests you want to have on. And I thought, oh, my gosh, Sarah Blakely, definitely, right? Like, I put this huge list together. And he said, you know what? I actually know Jesse Itzler and I know Sarah Blakely. Maybe there's a chance there. Can't promise anything, but maybe. You never know. It's worth trying, right? So again, I just put it out there who I was going after. He said, well, maybe this is one I could help with. Let's see what happens, you know, and just kind of leave it there. Well, for a while, nothing happened. And then one day he called me and he said, you know what I was thinking? I just had a call with Jesse's partner, his business partner. I could put you in touch with him. And who knows what can come from that conversation? At least it's something that might open up a door. So I said, great. So he sets up a call for me with Jesse's business partner. Gosh, this is so roundabout, the way that things come together. It's incredible. Serendipitous. And I had no idea if I'd ever get to her or get her on my show. So I take the call first Thing I ask is, how can I add value? Right? So we get on the phone. I said, listen, tell me how I can be of assistance, help to you, support you in any way. He starts telling me about this new initiative that they have two new business initiatives, and he was wondering if I could support it somehow, you know, through social media. I had my podcast at the time. Through my podcast, you know, what were some of the ideas? How could I add value to help support him? So I went through a bunch of different ideas that I had, and I actually had just met someone who in that space was, you know, doing some support work that I thought could add value. I said, I'll make an intro there, right? I was just talking about how can I add value to him. Always see things through that lens. How can we help others? And when you see through that lens first, you are just destined to have good things happen. Maybe not on that call, maybe not in that one exchange, but at some point, good's going to come back to you, keep leading with good, keep adding value to, uh, others. So at the end of that call, he says to me, I heard that you wanted to get Sarah and Jesse on your show. And I got to be honest with you, Sarah, absolutely not. You can't. And Jesse, he really doesn't want to do podcasts much anymore. He's too busy. I said, I totally get it. You know, no problem. I just appreciate that, you know, you took the call and whatnot. So, you know, I'm kind of getting a no at that point. We end up staying on the phone a little bit longer anyhow. He says, all right, can you make that intro to that other guy and contact you have? Sure, no problem. Appreciate it. Let's see where this goes in the future in any way I can help you. He had an event coming up, you know, I said, let me know if I can support that. Whatever. Move on. Okay. So the next day, I get a message from him after I make the intro, and he sends me text. Hey, I think I might be able to get Jesse to do your show. However, there's only a couple of dates, and it's not for a couple of months. And I said, no problem. Right? This is out of left field. Okay, no problem. Whatever it is, I'll make it work. So he connects me to Jesse's assistant, who gives me a couple of dates. I pick one, and I say, okay, I want to fly to Atlanta to interview him. She says, no, he only does zoom interviews. Okay, I'll take what I can get. No problem. Again, not fighting it. Make it easy, make it so simple that people want to work with you, want to be in business with you. So the day of the interview, Jesse's Internet kept going out. Yes. These people are billionaires with a B. And for whatever reason, serendipitous universe, something else, A, uh, higher power is at work here. The Internet kept going out. So finally I get a text message. It was from Jesse. I didn't know. I thought it was from the assistant. Says, listen, this is ridiculous and embarrassing. My Internet keeps going out. I'm sorry to have wasted your time, but it doesn't look like we're gonna be able to do the show. And I said, well, how about I jump on a plane and fly to Atlanta? It's only 45 minutes flight from Miami. And he said, would you really do that? I said, yeah, of course I would. Oh my gosh, it'd be amazing. Don't forget, my goal in the first place was to be face to face. Cause I always wanna be face to face with people. That's where the magic happens. That's where opportunity happens. That's where you can really move the needle. So he says, okay, how about next week? Uh, you know, today won't work, but what about next week? I said, sure, give me the day time, I'll be there. My best friends live in Atlanta. It's easy for me, no problem. So I fly up the next week, I go to his house, I interview him. We have such a great time. He's so, uh, nice, was so welcoming. Just such a cool guy. He mentioned that he liked my microphone. So as soon as I left, I bought him a, uh, microphone, overnighted it to him with a thank you note. Right. I'm always thinking, how can I make people feel special and act on the things that are important to them? And I just want to separate myself, right, and be thoughtful. And so when he received it, he sent me a text. He said, hey, thanks so much for that. That was really thoughtful of you. Appreciate it. If there's ever any way I can help you, let me know. So I said, thank you. I did not ask about trying to get Sarah for my show. I thought that might be a little bit much, coming in a little hot with another ask. Right after I got him to do my show, wouldn't you know, literally, a couple of weeks later, my very good friend Scott McGregor calls me and he says, you're not gonna believe this, but a sales and marketing conference is looking for someone to interview Sarah Blakely and Jesse Itzler live. On stage in front of thousands of people. And I was just talking to the event coordinator and your name came up because you already know Jesse. I had just met Jesse. We had hit it off. I had just promoted him on my show, right? So I was trying to do things to help support him and we had, you know, just gotten along during the interview. Super great guy, amazing entrepreneur, father, husband, great person. Anyhow, so cut to I end up getting hired to interview him and his wife live on stage. And I had so many meetings with Sarah's team and it was a lot going into it, right? And so I really wanted everything to go flawlessly. Of course it didn't. There was tons of problems and issues. But we had such a great time and the event coordinator was so happy with how our interview went that I went up to her that day of strike, um, while the iron's hot. And I said, will you allow me to repurpose this content on my podcast? It will give you reach. I will promote the heck out of your event. I will help you sell tickets for next year. Right? How can I add value to you? And she said, yes, I'll sign the release and let you repurpose the your interview on your show. Meet a different guest each week.

Speaker A: My personal philosophy when it comes to money is pretty straightforward. Your cash should always be working for you, not sitting idle while you figure out your next move. That's where Wealthfront comes in. They help you tune out the noise and earn more on every dollar with a high yield cash account and sophisticated easy to use investing products. With the Wealthfront cash account, your money can earn up to a 4.3% variable APY for a limited time. Get instant no fee withdrawals 24.7to eligible accounts and when you're ready, it's seamless to transfer funds directly into their expert built investing products. Right now. As a confidence listener, you can maximize the rate you earn. You'll get a 3.3% base APY from program banks. Plus new clients can get an exclusive 0.75% APY boost for your first three months up to $150,000 balance plus an additional 0.25% APY increase when you direct deposit $1,000 a month and open and maintain a funded investing account. The window is limited so don't wait. Join over a million people already building wealth with confidence. Head to wealthfront.com confidence to get started. Terms and conditions apply. This has been a paid non client endorsement of Wealthfront which creates a conflict of interest. Client experiences will vary. Wealthfront Brokerage is not a bank. The base APY is as of January 30, 2026 and subject to change. For more information, see the Episode Description Description area for disclosures to be added. This experience may not be representative of other Wealthfront clients and there is no guarantee of future performance or success. Experiences will vary. Heather Monahan and the Creating Confidence podcast collectively Media Partner are not clients of Wealthfront. The Media Partner receives cash compensation from Wealthfront Brokerage for this paid endorsement placed in their podcast, creating a conflict of interest. More details available via uh, the Referral link. The Direct Deposit plus Investing program from Wealthfront Advisors LLC and Wealthfront Brokerage LLC provides eligible clients a 0.25% APY increase above the base APY on eligible cash account balances up to an overall boosted rate of 4.3% for a limited time when including the 3 month 0.75% APY boost for new clients. When you direct deposit $1,000 a month plus open fund and maintain an investing account, Wealthfront may change or end the program at any time and determine eligibility at its discretion. Terms apply. Full details@wealthfront.com promoterms the cash account, which is not a deposit account, is offered by Wealthfront Brokerage LLC, member FINRA SIPC. Wellfront Brokerage is not a bank. The base APY is 3.3% on cash deposits as of 1-30-20, is representative, subject to change and requires no minimum. Funds in the cash account are swept to program banks where it earns the variable apy same day withdrawal or instant payment. Transfers may be limited by destination institutions, daily transaction caps and by participating entities such as Wells Fargo, the RTP Network and FedNow Service new cash accounts. Deposits are subject to two to four day holding period before becoming available for transfer. Investing involves risk including the possible loss of principal securities. Investments are not bank deposits, bank guaranteed or FDIC insured and may lose value. Investment advisory services are provided by Wealthfront Advisors LLC and SEC Registered Investment Advisor okay, if you've been wanting to make some money on the side and don't uh, really want to put your own face on a camera to do it, you can, you can make money on the side. You can make anywhere from $10,000 a month to $50,000 a month just being who you are, teaching the things that you're already an expert in and you can even use an AI avatar to do it for you. You don't have to have your face on camera anymore. So the idea now of Creator Income is available to you to anyone and there's no barrier to entry. It is so simple to do. You can create your own AI avatar and you tell it what to say. Now you're charging, you are getting reoccurring revenue every single month. And anyone can do this by just showing up and sharing your expertise. Teaching the things from Jiu jitsu to working out to how to cook, to how to bake bread, to how to create confidence. Anything that you're an expert in, anything that you're great at, you can now monetize the platform. It's already there, it already exists and it's easy to do. Why not start making your passion in life your side hustle and start getting 10 to $50,000 a month just showing up, teaching what you already know. It's easy, it's not hard to do and it's ready for you. You need to go to fanview.com to

Speaker B: set up your account.

Speaker A: Now it is so simple to do. Start making money on the side. It's www.fanview f a n v u e.com today and launch your career. What made me start taking creatine in the first place? I mean, if you're not taking creatine, what are you doing? We are losing muscle the older we get. You need creatine in your life. Creatine is one of the most researched and effective supplements available. That's why Momentous created Signature Spec Creatine, their most advanced creatine ever. Setting a new standard for creatine quality. Momentous Signature Spec Creatine is one of the only creatines to be manufactured in a pharmaceutical facility using reverse osmosis water purification and verified through an expanded six stage testing process with four independent agencies. And that means momentous creatine delivers 10 times fewer impurities, two to five times tighter heavy metal, limits, PFAS and microplastic screening, and more. They've even improved the product experience with an ultra fine powder that mixes effortlessly with no grit or clumping. The momentous standard, the relentless pursuit of better and what you can always expect with Momentous products. And the benefits of creatine are real. Support, strength, power, lean muscle growth, recovery and even improve cognitive performance. So if you're going to take creatine, take it every day. Make sure it's the best. Choose Momentous Signature Spec Creatine. It's the creatine I take and I will tell you, it is so much finer, so much stronger, so much better than everything else out there. If you want to try Momentous Signature Spec Creatine, head to livemomentous.com and use code confidence for up to 30, 35% off your entire first order. Livemomentous.com promo code confidence. I asked you to try to find your passion.

Speaker B: I'll tell you, you know, there's so many different ways to try to just keep adding value to people and just wonder, okay, I'm gonna keep adding value. I'll ask for what I want When I see the opportunity, I might not always get it in the moment, I'm gonna have that clear intention. I'm gonna keep showing up and adding value and keep knocking on different doors and. And eventually, you know, that hope is that those dots end up connecting. We don't know how. They always will, but in the end, most of the time they do. And if they don't, it wasn't really meant for us. Okay, so those are a few examples. Oh, here's another one. Ryan Serhant was another big name guest, millions of followers. This one happened so easily. So the Sarah Blakely one was definitely a bigger roundabout way, way more work, time, effort, et cetera. The Gary Vaynerchuk one, same thing like that did not happen overnight. That took a while, actually a couple of years to come to fruition. The Ryan Serhant one, though, you never know. I had a friend who was interviewing him for his podcast, and when he was about to get off his podcast interview with Ryan, he said, you know what, My friend has a really big show. Would you want to do her show? It's called Creating Confidence with Heather Monahan. He just asked for me. I popped in his mind and he said, sure, no problem. Put her in touch with my assistant and I'll go ahead and do it. So they had just hit it off and my friend offered up this opportunity. I hadn't asked him. I didn't have an intention to get this guy on the show. But we had talked before about, you know, the kind of guests I was looking for. So my point to this is there's gonna be times where things are a struggle and doesn't seem like they're lining up the way that you had hoped, and that's okay. And we keep moving forward with our vision and our work, right? And adding value and doing the next right thing. And then there's times things just fall in your lap. Such a good example of this in my life recently is when I got the call from Dr. Phil's producer, right? I was in the middle of my move. It was the worst time ever for me. Not like there's ever a Perfect time. And I just randomly got a bunch of DMs on social media saying, we need to have you on the show. Can you be here next week? And again, the timing was far from perfect. I was in the middle of a move, my first move in 17 years. But, you know, I thought, this is a once in a lifetime opportunity. It can help me reach a broader, larger audience. And if it's gonna help one person, I need to be there. I've gotta show up and make that happen, right? So it seemed like that just happened out of left field. Cut to when I got to know the producer better, which she's amazing. And we were talking, she explained it was my TED Talk that sold her on me. So it wasn't that I just randomly popped into this woman's head and, you know, fairies were just flying all around. But back in the end of 2019, I had worked incredibly hard on my 10 minute TED talk and somehow it was served up to her through the YouTube algorithm somehow. So I don't know how that happened. But this is one of those situations where we're going back to 2019, and really we're going back from beyond that. Because I had been speaking for years before I took that TED Talk, right? I've been Speaking for about 20 years in corporate America. So I mean, this road to get to the Dr. Phil show might look like it was seamless and just, uh, miraculous, but it really wasn't. It was years of me working on my speaking craft and then landing the TEDx talk, and then the TEDx talk getting promoted to TED and then somehow an algorithm serving it to the producer at Dr. Phil. So there isn't always rhyme or reason, but putting the hard work in does pay off. It just might not pay off in the moment. I remember at the end of 2019, my TEDx talk came out the night before Thanksgiving 2019, and feeling so deflated because nothing massive happened. I thought overnight I would have millions of views, like, in my mind, this is how it was gonna go down, and millions of opportunities, and it just didn't really happen. And in fact, a lot of the people in the speaking business, they weren't excited about my TEDx talk because they thought I should have done one on sales and sales leadership so that they could go out and sell it to corporate America. I did it around the elephant in the room that no one talks about women in the workplace bullying other women. And it was something that was really passionate to me and I want it to be different and unique. I can do a Million talks about sales and sales leadership. But this one story was something that was different, right? Nobody's talking about that. And I want to show up and be unique and different. And taking those kinds of risks doesn't always pay. So it was at end, the after the talk came out, I was a little discouraged, right? I was thinking, oh, my gosh, this kind of stinks. That I, maybe I should, uh, I started wondering, should I have done it differently? And here I am today, you know, almost three years later. I'm so grateful that I moved forward with my truth, that I took the risk on, um, being different and not showing up vanilla like everybody else. So my message to you today is you might not always see the payoff right when you put the work in, but have faith that those dots are going to connect, that things will come together. And the more you keep adding value, showing up as that real, true version of yourself, regardless of what anybody else thinks or says, things are gonna start working out for you. They are gonna come together for you. And you're gonna keep going bigger. You're gonna capitalize on that momentum and allow it to launch you forward towards your goals. Well, that's my hope for you anyways. And all of that is about creating confidence within yourself, believing yourself and taking the risk. Because so many of us freeze up and are afraid because we want it done, um, perfectly. We don't know if the timing is right. Well, I don't either. But I know I'm never getting back right now. So that's why I'm going for it. That's why I'm glad I took the flight to LA to do the Dr. Phil show, even though I had complete chaos going on in my life. It wasn't easy, but it was worth it. And I've received so many beautiful DMs from people from that message. So, you know, keep leading as that real version of you. Yes, it's not always easy. Yes, there's gonna be work that needs to go into it. But I believe in you. I believe that the best is yet to come for you. And you've gotta keep moving forward, taking chances and doubling down on you. If you like this episode, please share it on social media. Tag me. And when you do, I'm gonna repost it. I'm gonna appreciate it so much. Cause no one succeeds alone, including this girl right here. Until next week. Keep creating your confidence. You know I will be. I decided to change that dynamic. I couldn't be more excited for what you're gonna hear. Start learning and growing.

Speaker A: Inevitably something will happen.

Speaker B: No one succeeds alone. You don't stop and look around once in a while. You could miss it. Come on this journey with me.

Related episodes across the Index

Other episodes covering the same guests and topics, from across The B2B Podcast Index.

  • The Open Book Problem 1: How Your Public Records Become an Attackers' RoadmapThe Small Business Cyber Security Guy · on LinkedIn90 / 100
  • From 78 Emails to 4.7 Million Subscribers: The 1440 Story with Tim HuelskampGrowth In Reverse: Newsletter & Email Growth · on Sara Blakely88 / 100
  • Ignite Startups: How Adam Nash Built Daffy Into a $1B Donor-Advised Fund Platform | Ep281Ignite · on LinkedIn87 / 100
  • Dynamo's Nicholas Carlson on finding content-market fitThe Rebooting Show · on LinkedIn81 / 100
  • Great Salespeople Don't Sell with Rob DurantThe Business Development Podcast · on LinkedIn80 / 100
  • Ads in ChatGPT Are Coming. What B2B Marketers Should Do Right Now | Keith Delany, CEO PrimerThe GTMnow Podcast · on LinkedIn77 / 100

More from Creating Confidence with Heather Monahan

All episodes →
  • Confidence Classic: Why Your Next Breakthrough Could Be Closer Than You Think with Heather
  • Confidence Classic: How To Keep Moving Forward When You Feel Discouraged with Heather!
  • How to Find the People Who Will Help You Grow, Scale, and Succeed with Stephanie Cartin
  • Confidence Classic: 9 Ways To Build Unstoppable Confidence with Heather
  • Confidence Classic: This Is Your Year Of Possibility With Heather!
Explore the best B2B Leadership podcasts →
All Creating Confidence with Heather Monahan episodes →