Episodes

  • Brooklyn, Brews, and Botanical Breakthroughs with Hudson Davis-Ross, Co-Founder and CEO of Plant People

    Brooklyn, Brews, and Botanical Breakthroughs with Hudson Davis-Ross, Co-Founder and CEO of Plant People
    May 7 2024
    Description:Today, Hudson Davis-Ross joins the show to share about Co-Founding a mission-driven company that truly helps people with their health needs. From being diagnosed with ADHD in middle school to undergoing spinal surgery, Hudson has faced his fair share of health challenges. Tune in to learn all about his captivating entrepreneurial journey, from growing up in Brooklyn, New York, to founding his first company, RISE, to ultimately becoming the co-founder of Plant People – whose plant-based products offer natural alternatives to pharmaceuticals. Along the way, we explore how he navigated major setbacks caused by the COVID-19 pandemic and gain insights into his refreshing perspective on building purpose-driven businesses!Exclusive Deals from Our Sponsors:AWESOME CX by Transcom provides high-touch, personalized customer experience services to consumer brands of any size! Email Lee at lee@stairwaytoceo.com to learn more about their award-winning services and Awesome Coffee ChatsIn This Episode You’ll Hear About:• [01:54] What it was like growing up in New York, at the epicenter of so many industries, within a household dominated by women.• [06:43] Hudson’s ADHD diagnosis in middle school, the many different interests he pursued, and the benefits and drawbacks of having ADHD when you’re an entrepreneur.• [10:23] His experience working at Gilt Groupe from its early stages as a small startup to having over two thousand employees.• [14:13] Why he decided to leave Gilt Groupe and take on a role at Aloha as part of the founding team, and his top takeaways from the experience.• [18:25] What made Hudson shift to co-founding his first company, RISE Brewing Company, key lessons he learned, and how he met his partners.• [25:32] Fundraising for RISE, and how it led to him starting his branding and business strategy firm, CROSBY.• [27:29] The drastic spinal surgery that Hudson had to get, how it led to the founding of Plant People, and what it was like entering into the CBD and cannabis space.• [30:22] How they stepped up their business, educated consumers, and the innovations they were doing with regards to ingredients and formulations.• [32:42] Their decision to scale up, why they decided not to take on more funding, the dramatic impact that COVID-19 had on their revenue, and how they recovered.• [35:27] Hudson’s insights on partnering with retailers and distributors, advice for aspiring and up-and-coming entrepreneurs, and what’s next for Plant People.To Find Out More:Hudson Davis-Ross on LinkedinPlant PeopleRISE Brewing CompanyCROSBYGiltExpo WestLee Greene on LinkedInStairway to CEOStairway to CEO on InstagramQuotes:“I always hope to, at some point in my life, write a book on having ADHD and being an entrepreneur, because I think there's a lot of pluses and minuses – mostly pluses.” [0:07:19]“If you have [a] really big vision, and momentum with other investors, people will invest. It really is a hype game. And so I learned a lot around fundraising [at Aloha].” [0:17:12]“[To be] the Apple of anything – takes decades. You can't just do that [in a] matter of a year or two. But that's what we pitched [to] a lot of the investors. And so I think there was a bit of a disconnect there.” [0:18:43]“The main reason I started this business, [Plant People] is I had spinal surgery, [I had to] learn how to walk again.” [0:27:31]“My now co-founder also had a spinal surgery and was exploring plant-based modalities himself. And so we started together.” [0:28:01]“I had more passion for making an impact in people's lives.” [0:28:12]“We had so much pushback in the beginning because people didn't understand CBD. They thought it was weed. They thought it was THC, they were like, ‘Will I get high from this?’ That was the biggest education point.” [0:30:59]“Tap into what customers want [and] are already [buying], [but do] it better.” [0:36:09]“In general, you just got to hustle. You have to go with momentum, you have to have a lot of boutiques [and] a lot of independents. And when you have that momentum, then you can get the attention of distributors.” [0:36:27]“The secret sauce is to be an entrepreneur – is to use the resources you don't have, to achieve what you believe in.” [0:37:56]“You can hire sales managers who have been in sales, and they have rolodexes. And that does help. But I think no one sells better than the founder or the CEO.” [0:39:39]“One of the things that is key to success is showing your team, or showing your initial hires, that you're all in.” [0:41:06]“If you're doing it, the team can do it. And if you're passionate about it, the team gets passionate about it, they see the value.” [0:43:09]
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    45 mins
  • Widening the Wealth Circle for Women with Allegra Moet Brantley, Founder and CEO of Factora

    Widening the Wealth Circle for Women with Allegra Moet Brantley, Founder and CEO of Factora
    Apr 2 2024
    Description:Joining the show today is Allegra Moet Brantley, the Founder and CEO of Factora. This women-led personal finances company is on a mission to lead one million women to $1 million in wealth. Today she shares her journey from building her first company to becoming a salary negotiation coach to leading partnerships and marketing at Financial Gym, where she ultimately came up with the idea to build Factora. Tuning in, you’ll gain insight into the importance of financial transparency, the challenges that can come with fundraising, building a sustainable business while growing a family, and much more. Allegra also has some valuable, go-getting advice for aspiring entrepreneurs, so if you have a business idea that has been nagging at you, you won’t want to miss this episode!Exclusive Deals from Our Sponsors:• AWESOME CX by Transcom provides high-touch, personalized customer experience services to consumer brands of any size! Email Lee at lee@stairwaytoceo.com to learn more about their award-winning services and Awesome Coffee ChatsIn This Episode You’ll Hear About:• [02:53] Why transparency is the key to rid conversations about personal wealth of taboo.• [05:43] Insight into Allegra’s upbringing across the country, her education, and her first jobs.• [16:35] The importance of always negotiating for more and reading contracts thoroughly!• [19:45] Lessons from Allegra’s time in the marketing department at Estee Lauder.• [21:35] What her first steps into entrepreneurship in 2011 taught her about financial freedom.• [30:13] Allegra’s valuable experiences at Financial Gym and the origin story of Factora.• [38:29] How Factora has evolved and how The Wealth Circle community has grown.• [40:45] Some of the challenges of fundraising, bootstrapping the business from the ground up, combating burnout while raising a family, and how Allegra overcame them.• [49:37] Price ranges for Factora’s courses, what they entail, and how you can benefit for life!• [53:50] What the future holds for Factora, how they take women from overwhelm to sustainable wealth-building, why this industry is ripe for disruption, and more.To Find Out More:FactoraThe Wealth Circle6 Figure SavingsCoffee & Coin PodcastAllegra Moet Brantley on LinkedInAllegra Moet Brantley on InstagramLee Greene on LinkedInStairway to CEOStairway to CEO on InstagramQuotes:“It is so nerve-wracking and cathartic to share these numbers we never [talk about]. In the very first call, [Wealth Circle members] are sharing their salary.” [0:04:26]“When we share resources and investment strategies, it’s such a wealth of knowledge.” [0:05:33]“[Becoming] a salary negotiation coach – only reemphasized what I was experiencing personally. Now that I’m good at asking for more money [and] getting more money, it doesn’t mean I have more money. Making and keeping [money] are two very different things!” [0:29:02]“I was more passionate about helping women build wealth than anything else I had touched on in my career. It’s one thing to understand where your income goes. It’s a whole other thing to make a strategy for investing it [and] feel confident enough to do so.” [0:34:25]“It felt like a sentence would not stop tapping at the base of my neck – ‘Help women build wealth, help women build wealth, help women build wealth,’ all day long.” [0:35:51]“When you raise funding, and now you have investors involved, and they have a vision too, oftentimes you have to acquiesce and collaborate with that vision. I felt so strongly [about] my own [vision]. I didn’t want to bring in anything to muddy that.” [0:43:57]“90% of women come to Factora for the stick market portion. They say for the community and the access to additional creative investment ideas.” [0:52:32]“I don’t want people to hand over their entire financial autonomy because they don’t think they’re smart enough to do it themselves. That is why I think this industry is ripe for disruption.” [0:57:55]“For aspiring entrepreneurs; if you have an idea that’s banging at the base of your neck, it’s going to create value in this world both for potential customers but also for you and what you are going to learn [through your failures, strifes, and success]. Make like Nike and do it!” [0:58:20]“Investing is not hard. Investing is not complicated. You are meant to think – that it is. You’re already doing it if you’ve ever utilized a 401k or an IRA. You can do more of it, and I suggest that you do.” [0:59:49]
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    1 hr and 6 mins
  • Turnarounds, Transformations, and Taking Charge with Mary van Praag, Global CEO at Milani Cosmetics

    Turnarounds, Transformations, and Taking Charge with Mary van Praag, Global CEO at Milani Cosmetics
    Jan 16 2024
    Description:  Mary van Praag joins us today to talk about how she became Global CEO of Milani Cosmetics, a 20-year-old company built on the belief that everyone should have the opportunity to own and enjoy luxury beauty. From her entrepreneurial pursuits in high school to her first CEO role at Perricone MD, Mary tells us about her remarkable career journey and how she became the Global CEO of Milani cosmetics. Tune in today to learn about Mary’s passion for transforming companies, the lessons she’s learned about being vulnerable as a leader, and much more!Exclusive Deals from Our Sponsors:AWESOME CX by Transcom provides high-touch, personalized customer experience services to consumer brands of any size! Email Lee at lee@stairwaytoceo.com to learn more about their award-winning services and Awesome Coffee ChatsIn This Episode You’ll Hear About:[02:31] Mary’s upbringing in Ohio; how her parents’ divorce (and being the eldest) informed her early leadership development, her first entrepreneurial pursuits, and her college years.[10:12] What it was like moving 17 times in her professional life, how this has proven her ability to manage change, and why she loves making things better.[14:46] How Mary found her internal drive as a leader and her advice to others struggling to find their voice.[21:18] Her early career in sales and how her experiences as general manager at Coty and OPI Products set her on the path towards CEO.[27:07] Mary’s first role as CEO at Perricone MD, the destabilizing impact of the COVID pandemic, and how she adapted and ultimately became CEO of Milani Cosmetics.[30:54] Key lessons on building your team as a CEO.[34:44] What Mary has learned about turnarounds since she first started out, and her insights on how being CEO resembles running your own business.[37:53] Why being vulnerable as a leader is one of the most important lessons Mary has had to learn, and her thoughts on what sets the role of CEO apart from other positions.[46:02] Milani Cosmetics’ approach to remote work and an overview of the exciting things the brand has coming up![52:18] Mary’s practical advice for aspiring CEOs.To Find Out More:Mary van Praag on LinkedInMilani CosmeticsCotyPerricone MDLee Greene on LinkedInStairway to CEOStairway to CEO on InstagramQuotes:“Moving, I think, indicates my ability to manage change and transformation. But at the same time, create a great network of deep-seated roots and connections that I will forever have in my life.” [0:12:13]“I'm at my best, as a leader – when you look at the context of a situation – when something requires change and transformation. I love to make things better.”  [0:12:40]“Some people are great at constructive conflict, others are analytical geniuses, others are great teachers. I always say ‘find that thing that makes you unique, [and] whatever your superpower is, really feed into it.’” [0:16:14]“Leaders don't have all the answers. What I want to hear is the people [who] are closest to the business [and] have a unique point of view. And we need to hear that.” [0:16:56]“I can be interesting, but I have to be interested first.”   [0:19:54]“You always have to respect the past, but you have to get people aligned to create the new future. And you quickly find out who wants to do that, and who doesn't. And that's a lot of work.” [0:25:02]“Thinking about how you build teams is an important part of what a CEO does. I have amassed a fabulous team with very high engagement scores and a really strong culture. And we built it brick by brick, but it started with my leadership team.” [0:33:04]“We're all motivated towards the same future that we want to build. And that's very, very rewarding.” [0:33:51]“Depending on the circumstances, [a turnaround] this is like running our own business.” [0:35:26]“The biggest thing I had to learn was to be vulnerable.” [0:37:55]“If you don't give people an inspiring vision, they have nothing to hope for. Especially when you're in a turnaround.” [0:38:53]“I don't necessarily think everybody needs to be in the office every day to get productivity or work. I think we have happier employees, because we're hybrid, and that’s part of our culture now. We work hybrid.” [0:47:14]“Have a bias [towards] action. The strategic agility part is really important in today's day and age with the millions of things that we have flying at us.” [0:53:08]
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    55 mins
  • Connection, Community and Conversation with Julie Rice, Co-Founder and CEO of Peoplehood

    Connection, Community and Conversation with Julie Rice, Co-Founder and CEO of Peoplehood
    Jan 9 2024

    Description:

    Today’s guest fell into entrepreneurship when she started to create experiences with her own needs in mind. Julie Rice is the Co-Founder and CEO of Peoplehood, where she facilitates deep conversation and connection to develop ‘relationship fitness’. During this episode, she shares her childhood passion for theatre, talks about the start of her career in talent management in New York, and tells the story of how she built and exited her first startup, SoulCycle. Tune in to hear all this and more!

    Exclusive Deals from Our Sponsors:

    AWESOME CX by Transcom provides high-touch, personalized customer experience services to consumer brands of any size! Email Lee at lee@stairwaytoceo.com to learn more about their award-winning services and Awesome Coffee Chats. 

    In This Episode You’ll Hear About:

    • [02:16] How growing up as a theatre lover in small town New York started her off on a creative and collaborative path.

    • [06:24] Early leadership tendencies, working in the entertainment industry, and translating those skills to working in brand.

    • [12:44] The story of SoulCycle’s inception in New York in 200; starting with a business plan on the back of a napkin.

    • [17:11] Starting and growing SoulCycle and the premise that motivated Julie and her business partner to start Peoplehood.

    • [26:41] What Peoplehood is and how it is unfolding as a business.

    • [34:02] Tips for truly getting to know the people in your sphere.

    • [43:28] Communication insights from Peoplehood and advice for entrepreneurs.

    To Find Out More:

    Julie Rice on LinkedIn

    Peoplehood

    SoulCycle

    Awesome CX

    Lee Greene Email

    Lee Greene on LinkedIn

    Stairway to CEO

    Stairway to CEO on Instagram

    Quotes:

    “For me, the great fun in any business that I create is really about collaboration and the gifts that different people can bring to a project.” [0:06:34]

    “Community and team activity is something that I’ve always loved participating in.” [0:07:04]

    “A lot of the things that I learned in the entertainment business absolutely affected the way that I thought about brand building.” [0:09:55]

    “Brand is really about who you want to be in the world; what does it feel like, sound like,, what does it smell like, what does it look like?” [0:10:13]

    “The funny thing is, I never set out to be an entrepreneur. I never actually thought of myself that way until people started to use the word retroactively.” [0:15:14]

    “We created something that we wanted to use.” [0:15:31]

    “As an entrepreneur, having a business partner, if you can find the right partner, is great.” [0:18:14]

    “We began to think about what it would look like to create something that was relational fitness; a place where we could teach people how to listen to each other, how to talk to each other and build a different kind of muscle.” [0:23:13]

    “When you look at all the information out there, what we know for sure is that we cannot lead physically or mentally healthy lives without being in productive relationships.” — Julie Rice [0:24:17]

    “We spend so much of our lives and our time in relationships and we really don’t spend the intentional time figuring out how to be in these relationships.” — Julie Rice [0:24:49]

    “What people really want from people they are in relationships with is to feel heard by them, to feel seen by them, and to feel like their opinions matter to somebody.” — Julie Rice [0:27:29]

    “What we’re doing at Peoplehood is really giving somebody space to peel the layers of their own onion.” — Julie Rice [0:31:46]

    “An underpracticed and underappreciated skill is listening.” — Julie Rice [0:33:28]

    “There’s something about stepping back and letting someone finish that is very powerful.” — Julie Rice [0:42:00]
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    47 mins
  • Behind the Frames with Nathan Kondamuri, Co-Founder and CEO of Pair Eyewear

    Behind the Frames with Nathan Kondamuri, Co-Founder and CEO of Pair Eyewear
    Jan 2 2024
    Description:Nathan Kondamuri didn’t know that he wanted to start a business until the pieces fell together, and he co-founded the highly customizable Pair Eyewear, where he now acts as CEO. He joins us today to share the story of how his little brother inspired him to start Pair, how he scaled his customer experience team to over 100 members, and the challenges he faced in building on-demand production. Tune in to hear all this and more!Exclusive Deals from Our Sponsors:AWESOME CX by Transcom provides high-touch, personalized customer experience services to consumer brands of any size! Email Lee at lee@stairwaytoceo.com to learn more about their award-winning services and Awesome Coffee Chats. In This Episode You’ll Hear About:• [02:22] Signs of an inherent love for iteration and business development from Nathan’s childhood in small-town Indiana.• [10:58] His growing interest in mechanical engineering and his introduction to the start-up world beyond college.• [17:00] How Nathan and his best friend had the idea for Pair in a Stanford dorm room.• [20:58] Researching customers of all ages, early angel capital fundraising, and annual growth since launching to market in 2019.• [26:59] Pivotal moments in Pair Eyewear’s distribution and growth, including building a design platform for customers to bring their favorite brands to life and blowing up on TikTok.• [30:27] Scaling challenges like developing the on-demand production process.• [35:57] The secret to structuring a team with the support of Awesome CX.• [40:08] Pair Eyewear’s five-year focus to deliver a joyful customizable eyewear experience.• [46:59] Why, given a do-over, Nathan would hire people in key areas earlier, how his role as co-CEO has changed, and advice for new entrepreneurs.To Find Out More:Nathan Kondamuri on LinkedInPair EyewearPair Eyewear on TikTokLee Greene on LinkedInAwesome CXStairway to CEOStairway to CEO on InstagramQuotes:“I didn’t know I wanted to start a company – until Pair came about and one thing led to another.” [0:12:53]“[My experience at Bain] gave me a very different way of looking at a business – I got to learn a lot about how a business runs, and how experienced people view and understand a business model.” [0:16:02]“I had worn glasses since I was seven or eight years old, and it had always been an unexciting experience compared to any other consumer product in my life.” [0:17:31]“We got to thinking, why had nobody ever tried to [recreate, redefine, and redesign] the glasses experience for consumers to be more personalized, to be more joyful, and dynamic, just as people are?” [0:18:14]“We just knew we liked each other, we were really good friends and had been friends for four years, we had this idea, and we were excited to put our everything into that idea.” [0:20:04]“Surround yourself with people that are absolute experts at their craft, at their area of expertise.” [0:24:26]“We quickly, not pivoted, but expanded our mission and vision for the business to be able to personalize the eyewear experience not just for children, but for all people.” [0:26:23]“We were trying to build a solution for kids like my brother to not be afraid of their glasses and not be daunted by the experience, but have it be something they were excited about.”  [0:26:40]“We were a real pioneer on the platform of TikTok where we grew heavily on the platform through an influencer-led strategy.” [0:27:34]“Our mission and vision over the next five-plus years is to become one of the largest global eyecare companies in the world that’s focused on bringing personalization into the eyecare and broader eyewear end-to-end experience.” [0:40:08]“We thought a lot about, when is the right time to vertically integrate? You really want to do it at a time when volume and demand is growing.” [0:45:33]“The job of co-CEO now is not the same as it was when we first started the business.” [0:48:59]“Just get out and start! That is one of the biggest roadblocks that people have.”  [0:50:50]“The only way to learn what it’s like to be a founder is to just dive right in and do it.” [0:51:20]“Starting a company is a marathon, not a sprint.” [0:52:31]
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    54 mins
  • Wrinkles and Wins with Courtney Toll, Co-Founder and CEO of Nori

    Wrinkles and Wins with Courtney Toll, Co-Founder and CEO of Nori
    Dec 26 2023
    Description:Joining us today to share her entrepreneurial story is Courtney Toll, co-founder and CEO of Nori, an innovative company in the ironing and steaming market. Tuning in, you’ll hear about her remarkable journey, from coming up with the idea for Nori (which is iron spelled backward!) in her cramped New York apartment to raising money in the depths of COVID to bringing a successful product to market. Courtney also shares details about how learning to do cold outreach at her job bolstered her entrepreneurial journey, the challenges of innovating with hardware, how they put together their distribution and branding strategy, and much more. You won’t want to miss this fascinating deep dive into the many intricacies of hardware innovation and what goes into making your vision happen!Exclusive Deals from Our Sponsors:AWESOME CX by Transcom provides high-touch, personalized customer experience services to consumer brands of any size! Email Lee at lee@stairwaytoceo.com to learn more about their award-winning services and Awesome Coffee Chats.     In This Episode You’ll Hear About:• [05:11] Courtney’s idyllic childhood in Connecticut, her lifelong perfectionism, the legacy of entrepreneurship in her family, her early jobs, and how her career goals evolved.• [11:48] Key skills she learned from cold outreach; how this supported her entrepreneurship.• [15:59] How she got the idea for Nori while living in a cramped New York apartment.• [18:37] Courtney’s research; what she learned from interviewing over 500 consumers.• [21:17] How she and her co-founder overcame the challenges of innovating with hardware.• [26:19] Insight into their unexpectedly long product development process and how they implemented their distribution and branding strategy.• [30:15] Raising money in the depths of COVID, the far-reaching usefulness of a demo video, and how having difficulty fundraising worked to their advantage.• [38:27] Reflections on organic marketing and how to partner with the right influencers.• [43:44] Their company’s approach to marketing and the primary lesson Courtney has learned about building a successful marketing stack.• [46:22] What’s next for Nori, including launching some exciting new products, and parting words of advice for aspiring entrepreneurs!To Find Out More:Courtney Toll on LinkedInNoriLee Greene on LinkedInStairway to CEOStairway to CEO on InstagramAwesome CXQuotes:“I'm so grateful that I have gone on this path. And when I reflect on the things that are decisions that my family members made, I think it makes a lot of sense why I also went down this road.” [0:11:07]“There's always more to be done, there's always growth to be seen, and therefore, I push myself quite hard to succeed.” [0:11:33]“My co-founder and I ended up interviewing over 500 plus consumers to talk about what they liked about their existing ironing and steaming solutions, [and] what they didn't like.” [0:19:17]“It wasn't easy by any means. But we also weren't pitching this random idea and asking for a very subjective 300,000 [dollars]. At that point in time, we had outlines [of] exactly where all of this money was going to.” [0:23:20]“By the time that it was fully deployed, we had a working prototype and a lot of consumer feedback to validate the fact that we had stumbled onto something that we should take to market.” [0:24:25]“We decided on one product development firm, a satellite office in China.” [0:26:30]“With something like hardware, you do need to take your time really trying to get something right and [make] sure that it's giving you the desired output that you're looking for.”  [0:27:24]“The ironing steaming market is one that lives almost exclusively in big box retailers.” [0:29:06]“We wanted to be a direct consumer business, we wanted this to be a one-to-one conversation with the customer. And we wanted to make this a really cool branded sexy purchase which feels totally in conflict with a product like an iron.” [0:29:16]“Everything from our branding to the design of the product to the actual performance of the product was designed to sort of change the way you think about this type of chore.” [0:29:33]“[With a demo video] you're not just hearing a testimonial about why you like [a] product, but you're actually watching it.” [0:33:22]“I think the key takeaway here is building a marketing stack to support your direct consumer channel but making sure that all of the aspects of that marketing stack are feeding one another.”  [0:44:58]
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    46 mins
  • Travel Inspiration for Makeup Innovation with Fiona Chan, Founder & CEO of Youthforia

    Travel Inspiration for Makeup Innovation with Fiona Chan, Founder & CEO of Youthforia
    Dec 19 2023
    Description:

    Joining the show today is Fiona Chan, the Founder and CEO of Youthforia, a beauty brand creating innovative makeup that acts as a part of your skincare routine. Join us as she shares her story of starting a business during the pandemic, self-funding before finding Shark Tank support, and much more! 

    Exclusive Deals from Our Sponsors:

    AWESOME CX by Transcom provides high-touch, personalized customer experience services to consumer brands of any size! Email Lee at lee@stairwaytoceo.com to learn more about their award-winning services and Awesome Coffee Chats. 

    In This Episode You’ll Hear About:
    • [01:56] Fiona paints the picture of her early life, education and early jobs.
    • [10:44] Working in tech and a startup accelerator before becoming a founder. 
    • [14:41] How travel inspired the Youthforia brand and the hands-on process behind perfecting the product. 
    • [21:06] Building the brand on social media through storytelling and education. 
    • [24:49] Solving the funding problem through prioritizing inventory.
    • [25:48] The Shark Tank experience and the story of getting funded.
    • [29:21] Navigating new ways to get necessary data in a B2B context. 
    • [31:32] Product development and what’s next for Youthforia. 
    To Find Out More:

    Fiona Chan on LinkedIn

    Fiona Chan on Instagram

    Youthforia 

    Youthforia on TikTok

    Lee Greene on LinkedIn

    Stairway to CEO

    Stairway to CEO on Instagram

    Awesome CX

    Quotes:

    “You learn so much through osmosis.”  [0:12:13]

    “There was something about the pandemic that really made me think about what I actually wanted to do.” [0:14:13]

    “The sharks, the way I perceived it, really love and support entrepreneurship and enjoy what they’re doing. They’re really happy to see deals go through” [0:27:24]

    “When I had the idea to create makeup that you could sleep in, my first idea was to make a really nice foundation.”  [0:28:42]

    “When you switch from a purely B2C business to having a few sales channels, you don’t get data the same way as you would directly from Shopify.”  [0:29:22]

    “Once you have a retail partner, there are more complexities, especially on the operations side.” [0:30:06]

    “I did not start this business to be in legal docs and spreadsheets all day, but it is a big part of fundraising.” [0:30:58]

    “I am always in a state of product development. I would say that product development is my number one passion in what I get to do.” [0:31:39]

    “I always like to tell people exactly what to expect from me.” [0:32:18]

    “Finding people whose working style aligns with mine has been really helpful.” [0:34:24]

    “I really love sitting down and just defining what I expect in a role and what the best outcomes are. Doing that really makes the hiring process a lot easier” [0:34:52]

    “When I onboard people, I tell them, this is what you can expect from my personality and my working style.” [0:35:07]

    “My biggest advice would be just to start. It’s never going to be the right time.” [0:36:28]
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    39 mins
  • Making it Rain, One Square at a Time with Jake Karls, Co-Founder and Chief Rainmaker of Mid-Day Squares

    Making it Rain, One Square at a Time with Jake Karls, Co-Founder and Chief Rainmaker of Mid-Day Squares
    Dec 12 2023

    Description:

    As an entrepreneur, it can be tempting to try to master every aspect of the business, but today’s guest is proof that playing to your strengths and finding a partner with complementary skills is a winning formula. Jake Karls is the Co-Founder and Chief Rainmaker of Mid-Day Squares, a chocolate company geared to revolutionizing the snack industry. Join us as we discuss Jake’s unique path to entrepreneurship success, the decision to manufacture Mid-Day Squares in an independent factory, and the effect of digital transparency on relationship-building. Don’t miss today’s high-energy episode! 

    Exclusive Deals from Our Sponsors:

    AWESOME CX by Transcom provides high-touch, personalized customer experience services to consumer brands of any size! Email Lee at lee@stairwaytoceo.com to learn more about their award-winning services and Awesome Coffee Chats.

    In This Episode You’ll Hear About:

    • [02:21] Lessons of hard work and resilience he learned from his entrepreneurial father.
    • [10:12] Jake’s first foray into entrepreneurship; running an outdoor boot camp.
    • [12:10] Co-founding Mid-Day Squares with his sister and brother-in-law in 2018.
    • [20:51] Defining the roles and navigating the relationships behind the business.
    • [24:09] A year-by-year look at the growth behind Mid-Day Bars since its inception.
    • [28:13] How transparency has supported the fundraising process.
    • [33:10] What happens when envy and insecurity affect our attitudes toward others.
    • [36:39] Jake’s two experiences with burnout and his recovery process.
    • [40:06] The story behind Mid-Day Bars.
    • [42:21] Advice for aspiring entrepreneurs and a glimpse into the future of Mid-Day Bars.

    To Find Out More:

    Jake Karls on LinkedIn

    Jake Karls on Instagram

    Mid-Day Squares

    Lee Greene on LinkedIn

    Awesome CX

    Stairway to CEO

    Stairway to CEO on Instagram

    Quotes:

    “I know [that] anything is possible as long as you work hard and you have that resilience, that grit and love and passion for what you do.” [0:03:36]

    “If you work hard and put your effort and love into something, you have a chance of winning in that field.” [0:05:45]

    “Through my [first] five years of entrepreneurship, I learned not to do what I’m really bad at, and to do what I’m really good at [instead].” [0:12:51]

    “When you are yourself, truthfully, you are your best version and you are unstoppable because nobody can actually be you.” [0:16:30]

    “Our strategy was simply not to talk about the product on social media, but to share the journey of how we built this business.” [0:24:32]

    “We build out loud.” [0:28:57]

    “I feel like I’m playing the game better than I ever have before because I lost that ability to be – envious or judgemental.” [0:35:35]

    “My advice is block out the noise and be yourself.” [0:42:23]

    “Being yourself is a superpower.” [0:42:43]

    “We’re doing it by being ourselves which means that you can do anything by being yourself as well.” [0:43:20]
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    45 mins