Less Than Likely

Less Than Likely

Welcome to Less Than Likely, a podcast about the honest, behind-the-scenes stories of real entrepreneurs and their less than likely journeys of creating successful businesses.

Episodes

  1. Super Gratitude: Taking on something new in your business

    07/19/2022

    Super Gratitude: Taking on something new in your business

    Kate and Scott debrief the whole first season, through the lens of doing something for the first time in your business — in this case, a podcast! Producing our first season of Less Than Likely together brought a lot of lessons, discomfort, new experiences, surprises, and above all, amazing conversations. We dive into what it feels like to commit to something new, with another person, and what we’re taking away from it all. This is a blast of an episode, and leaves us feeling super excited for what’s to come in Season 2 of Less Than Likely!  Where the conversation went: Kate introduces Scott to a brand new game to play with friends. (It’s super fun — try it after your next family dinner or dinner party).We talk about all that was activated for each of us in agreeing to work together on this project — fear, trust, perfectionism, and being out of practice as collaborators.Kate and Scott go through a series of questions that we ask each other: What did you learn and are continuing to learn? What was scary and continues to be scary?What surprised you and continues to surprise you?What did you love?What are you looking forward to?Big themes: trust in collaboration, learning how to be visible as a business owner, balancing the different roles and experiences as a host and a human, the vulnerable moments of being an entrepreneur, and Scott’s genius editing skills. We talk about our favorite moments throughout the season, and what we’re most excited about as we start planning for next season. More guests, more experts, more Kate and Scott. Stay tuned!  Links: Subscribe to the podcast on Apple Podcasts, Spotify, Google Podcasts or your platform of choice to be notified of new episodes, coming Fall 2022.  Send us a noteFollow us on Instagram @lessthanlikelypodcastScott’s biz: The Curious LifeKate’s biz: KJT CoachingFollow them both on Instagram @kjtcoaching and @the_curiouslife Please rate and follow!  Every bit helps us as we launch.  Thanks!

    38 min
  2. Sybil Grieb, Digital Marketing Expert

    07/05/2022

    Sybil Grieb, Digital Marketing Expert

    Our first Less Than Likely "expert episode" features Sybil Grieb, digital marketing expert, Founder of 100 Hats, and SVP of Brand Partnerships at Whalar. It was so fun hearing Sybil’s less than likely story of starting her own agency and then pivoting to where she is most excited to grow her expertise. We get into the nitty gritty of all things social media and influencer marketing: where to focus when you’re starting out, how to research your competitors, what to do when you’re ready for paid marketing, and how influencer marketing can be a strategy at any stage. Where the conversation went: Sybil’s less than likely story of starting a business “accidentally” while taking a vacation.The moment when Sybil had to decide whether she could build her business in the way she wanted while staying in the lane of what she really loved to do, and how she decided to pivot to her position at Whalar ultimately. Sybil shares what to focus on in your first few years of building a business, in terms of both structure and marketing.How to research and assess for your own purposes your competitor’s strategies and positioning, so you can communicate your offering in a way that differentiates you and speaks to your audience.How to precisely assess and “arm yourself with facts” about how your competitors are doing so you can apply that research to your own business. The three places you need to focus your marketing with a tight budget. How to choose the right platform for your specific audience and test messaging to find the ones that resonate.When you are ready for paid marketing; what do you need to have in place and the tools to make it easier on yourself. What is influencer and creator marketing and why it’s so effective. How to get started with influencer marketing at any stage.Why we have hope for social media.Kate and Scott debrief. Links: Sybil’s company 100hats100hats.co on InstagramWhalerPlease rate and follow!  Every bit helps us as we launch.  Thanks!

    1h 6m
  3. Natasha Case and Freya Estreller, co-founders of Coolhaus Ice Cream and Future Gin

    06/21/2022

    Natasha Case and Freya Estreller, co-founders of Coolhaus Ice Cream and Future Gin

    Natasha Case and Freya Estreller had just started dating when they founded Coolhaus, a truly delicious ice cream company that quickly became a favorite brand of this generation. They walk us through their many times over less-than-likely story and how they’ve navigated building their business, starting a family, creating another business - Future Gin, the first fully woman-owned, operated, and distilled gin in existence, and Coohaus’ acquisition by The Urgent Company. Grab a Coolhaus ice cream sandwich and /or Future Gin & tonic and enjoy this super fun episode! Where the conversation went: It’s clear that “less than likely” is Natasha and Freya’s preferred mode of operation after hearing their story of creating the company, just as the two were starting to date, and launching into a competitive market in their 20s with zero experience. Natasha shares how Coolhaus started as an art project to bring fun and levity at the beginning of the Great Recession. How they launched their brand in a beat up postal van and quickly had to figure out how to scale in order to feasibly sell to their market at Coachella. They share how they made the leap to co-manufacturing to meet demand, and how their conviction, chemistry, and people taking a chance on them made all the difference. How they expanded from one to many trucks, to brick and mortar shops, to consumer packaged goods (CPG) in Whole Foods, through to acquisition. They break down their business model and how they made it happen. The first big investment as they pivoted to CPG and became a household ice cream brand. They share their branding mistakes as they expand into Whole Foods with Freya’s motto “Build, measure, learn.”Freya and Natasha talk about how it’s been navigating their personal relationship alongside their business, and when things had to change for them. We also hear about the benefits of being in business together when you’re starting a family, and how Freya and Natasha juggle it all - two kids, two businesses, and more. On top of everything they had going on, Natasha and Freya decided to join forces with two friends to create a brand new business in a whole new industry, Future Gin.Natasha shares some of the lessons they carry from Coolhaus into Future Gin and how they want to be active in their communities.As a mission-focused company, Natasha and Freya share how they bring that to their culture, their decisions, and ultimately how it informed their acquisition by a company that represents a new innovation geared towards healing the planet, The Urgent Company. They share the dramatic and stressful acquisition process, culminating in making the deadline with only 4 minutes to spare! Natasha shares what it’s like to transition to The Urgent Company as Chief Branding Officer, and lessons learned (and learning) there. Kate and Scott debrief. Links mentioned in the episode: Coolhaus websiteFollow Coolhaus on InstagramFuture Gin websiteFollow Future Gin on InstagramThe Urgent CompanyLearn more about Perfect DayPlease rate and follow!  Every bit helps us as we launch.  Thanks!

    1h 6m
  4. Eva Woolridge: Photographer, Public Speaker, and Activist

    06/07/2022

    Eva Woolridge: Photographer, Public Speaker, and Activist

    Eva Woolridge is an award-winning Queer, Black & Chinese portrait photographer, public speaker, and social activist based in Brooklyn, NY. In this conversation, we hear about her artistic process and how she navigates the integration of artistry and entrepreneurship, and how her career has shifted as her work becomes more visible. Eva offers her perspective on art and healing, considering social responsibility in photography, as well as how she chooses partnerships and projects. It’s a real gift to talk to Eva at this stage in her career; while already incredibly accomplished, it’s clear Eva is just getting started with so much more to come.  Where the conversation went: Eva’s less than likely nature stems from being self-taught in all aspects of the work she pursues as a professional, and we hear her journey to claiming her role as a professional photographer. Eva’s photo series “The Size of a Grapefruit” is a reflection on her personal experience of a traumatic medical event. We discuss the power and the pursuit of healing in sharing our own stories, and Eva shares her own realizations about sharing her experiences with others and its impact on her own healing process.Eva’s balance of corporate and personal work as a professional photographer, and how she has navigated her transition from receptionist to full-time professional photographer. Eva’s documenting of the Black Lives Matter protests in the aftermath of George Floyd and Breanna Taylor’s deaths was a pivotal moment in her career. Her photos were featured In Rolling Stone and other publications, and the treatment of her by white photographers during the protests sparked the creation of her Skillshare class: Socially Responsible Photography: Photographing with Intention, as well as led to public speaking opportunities throughout the country.How Eva considers the opportunities that come her way from the artistic, activist and ethical perspective. What she wants from the corporations as they think about who to hire for their next photoshoot. Eva shares some of her teachings regarding photographing both in and out of your own community and how to honor the role of the subjects in your own photography work. Eva shares details of her most recent venture, traveling cross country documenting Black Birth-workers and their history, experience and stories. Kate and Scott debrief.  Links mentioned in the episode: Eva Woolridge PhotographyFollow Eva on InstagramEva’s Leica Award-winning photo series: The Size of  GrapefruitEva’s TEDx talk: How we use art as a vessel to heal our traumaEva’s Skillshare class: Socially Responsible Photography: Photographing with IntentionSupport Eva’s Black Birthworkers DocumentaryPlease rate and follow!  Every bit helps us as we launch.  Thanks!

    1h 4m
  5. Kerstin Martin, Squarespace Educator and Creator of the Calm Business Movement

    05/24/2022

    Kerstin Martin, Squarespace Educator and Creator of the Calm Business Movement

    Kerstin Martin, Squarespace Educator and Creator of the Calm Business Movement calls herself an accidental entrepreneur. Her experimental nature and commitment to anti-hustle has helped her to build a business she loves to run and grow, providing online courses and community for thousands of solo business owners and their own growing businesses. We have a great conversation about what a calm business looks like, and how we can all achieve it. Where the conversation went: We dive right into Kerstin’s unique way of being as an educator and entrepreneur, including her commitment to anti-hustle.Kerstin introduces the concept of a Calm Business and the creation of her Calm Business Review, which you can download for free from Kerstin’s site.Why Kerstin calls herself an accidental entrepreneur and how she found herself with a successful online business. What does a calm business look like? Kerstin talks about her experimental nature and its role in her business.It becomes clear that Kerstin had created multiple “businesses” and careers in her past before launching her current iteration.The importance of a safety net, and what that means.Kerstin breaks down the many courses she offers and how they support solo business owners.The question of how to grow in an unexpected way, without taking on a big team or run ads, etc.Why anti-hustle is so important to Kerstin and all of us.Kate and Scott debriefLinks mentioned in the episode: KerstinMartin.comCalm Business ReviewBiz Box and Kerstin’s many online coursesPlease rate and follow!  Every bit helps us as we launch.  Thanks!

    48 min
  6. Susie Sarich of SusieCakes

    05/10/2022

    Susie Sarich of SusieCakes

    Susie Sarich, Founder and CEO of SusieCakes, created a whole new industry before there were any multi-unit from-scratch bakeries in the US. She shares the many challenges she went through to bring dozens of stores to California and Texas (and expanding) over the past 20 years, including the naysayers along the way who questioned the viability of her business model. This conversation is so rich and delicious, and a true celebration of connection — just like a Susie Cake.  Where the conversation went: Susie shares how SusieCakes’ story is rooted in memories from her two grandmothers’ kitchens, and the life lessons she learned from them.Susie witnessed women leaving the hospitality industry in droves — an industry that she loved and was passionate about — and set out to create a model that allowed women to have progressive careers in the industry without making them work nights and weekends and holidays.The lightbulb moment when the idea for SusieCakes all came together. Susie talks about how the model for SusieCakes was built extensively around the mission of connecting through celebration, something that she saw was missing in people’s lives. And that we all still crave 20 years later.Susie’s soon-to-be successful business was rejected by bank after bank after bank, where she was told that “baking is not a viable business.”Less popular in 2004 than it is today, Susie began crowdfunding for SusieCakes after striking out with traditional funding methods. Even with the naysayers, Susie was certain in this business. She shares what kept her focused on where she knew it was going.The moment when Susie knew when she knew SusieCakes was truly on its way.And then Covid. Susie gets real and honest about how devastating Covid was for her and the business, and how they coped through it.Susie gives advice to new or aspiring entrepreneurs. As always, Kate and Scott discuss their takeaways from the conversation. And Kate orders a SusieCake for her daughter’s birthday. Update: It’s unbelievably delicious and a special way to celebrate!Links: Susie Cakes (Order here for nationwide shipping) Please rate and follow!  Every bit helps us as we launch.  Thanks!

    50 min
  7. Deanna Taylor-Heacock of Good Bottle Refill Shop

    05/03/2022

    Deanna Taylor-Heacock of Good Bottle Refill Shop

    Saving the planet was the furthest thing from Deanna Taylor-Heacock’s mind when she got the idea to open Good Bottle Refill Shop, the first refill shop in New Jersey. What started out as a way to save time and money as a mom became a zero waste mission and business model to meet it. In a society where convenience is king, Deanna talks about how she’s educated herself on eco-friendly practices, sourced and developed products and processes, and built a circular economy - with the biggest hurdle being how to convince consumers to stop buying their trash.  Where the conversation went: Deanna shares how she didn't ever recycle until she was almost 30 years old and didn't much care about it, making her very less than likely to open the first ever refill shop in New Jersey.Deanna's aha as a stay-at-home mom trying to minimize trips to the store and how very much money was going out the door to big box stores became Good Bottle's main message: Stop buying your trash. Despite being the most densely populated state in the US, New Jersey did not have a refill shop until Deanna created one. We talk about the barrier of convenience being such a motivating factor in people's shopping experience and how refilling asks them to do something very different than what they've been sold in the past. In discussing the financial costs and benefits of refilling, Deanna invites us to consider what the cost to the consumer would be for non-refillable providers that we all use every day to take responsibility for the waste their product is creating.Deanna shares what it’s like building a business where there’s no one to really compare yourself to, as well as all the factors you have to figure out as you go with a new model of business.What it requires of a business to teach consumers a totally different way to shop and think. Links mentioned in the episode: Good Bottle Refill ShopBea Johnson's Zero Waste HomeUnpaper towelsAthos Please rate and follow!  Every bit helps us as we launch.  Thanks!

    47 min
  8. Erin Loos Cutraro of She Should Run

    04/26/2022

    Erin Loos Cutraro of She Should Run

    Erin Loos Cutraro is the Founder of She Should Run, a non-partisan nonprofit organization working to dramatically increase the number of women running for office, promoting leadership and encouraging women from all walks of life to run for public office. While women are elected at the same rate as men - when they run for office - they are less likely to see themselves in that role, which means they are seriously underrepresented. This conversation with Erin is eye-opening and inspiring, both from a civic duty perspective and from a business perspective, as she details the unique challenges and experiences the organization has faced over the last 11 years.  Where the conversation went: Curiosity, impatience, persistence: Erin shares how her entrepreneurial spirit was infused in her at a young age, from the women around her who were constantly figuring out ways forward, despite barriers.Erin walks us through her entry into politics and how the case for She Should Run builds as she navigates politics in her career: "it mattered who was in the room advocating for change" and it needed to include more than one type of candidate.She Should Run is filling the gap of identifying the women who previously would not see themselves as running for office and bringing them to the starting line of considering it.We talk about the challenges that She Should Run faces in getting women to see themselves in this role. First, imposter syndrome when they've been encouraged to run. And second, the core business challenge of targeting and learning about someone who's not even there yet. The person who doesn’t even have the possibility on their radar.We also talk about the fact that for women, signing up for politics can be a hard case to make, given the barriers and challenges faced - generally and right now.And what happens when you get what you want in your business, but for surprising and upsetting reasons? The moment after Trump gets elected and 1000s of women join the She Should Run community.The work is getting harder for She Should Run. How do you shift to respond to the very real demands and experiences that women and society are facing over the past two years. Erin leaves us with actions we can all take: Visit SheShouldRun.org and join their community, sign up for their newsletter. Programs are free of charge and noncommital. And support their cause through a donation. You can donate here: https://bit.ly/3MFg2f5 Links mentioned in this episode: She Should Run Erin’s TedX talk: Who Will Lead Us? You Already Know Her.Donate to She Should RunPlease rate and follow!  Every bit helps us as we launch.  Thanks!

    59 min
  9. Sas Petherick of Self Belief School & Self-Belief Coaching Academy

    04/18/2022

    Sas Petherick of Self Belief School & Self-Belief Coaching Academy

    It’s fitting that our first guest is our good friend and mentor, Sas Petherick, Founder of the Self-Belief School and Self-Belief Coaching Academy, from which both Kate and Scott are certified. Sas is radically changing the course of the coaching industry and humanity’s relationships with self-doubt through evidence-based tools and techniques that help you navigate self-doubt and cultivate tangible and sustainable self-belief, self-acceptance, self-worth, and self-trust. We go deep in this episode from the jump and stay there, with plenty of laughter mixed in. She is simply hilarious, brilliant, and an absolute joy to chat with. Where the conversation went: Sas’ personal story of getting sober and leaving her corporate job highlighted how traditional work environments reward many behaviors we now would recognize as trauma responses — excessive overwork, numbing behaviors, using humor to deflect conflict, and more.Sas’ hilarious retelling of her exit from her corporate job - “she wrote a poem that came true, and then visited a shaman” has us all giggling and unpacking the moment when everything changes in your career and life.We discuss the unusual declaration of “actually liking oneself” and how disconcerting that can be for others to witness.Kate wants to know all about the moment in Sas’ coaching business when she knew it needed to change again, and Sas shares how Self-Belief School and Self-Belief Coaching Academy (SBCA) were born.Sas drops a truth bomb about our ability to discern risk vs. opportunity when we are in burn-out.Scott and Kate share how SBCA bridged a massive gap they were experiencing in their own coach training and in the coaching industry in general.We discuss how we’re typically taught to navigate doubt (get into conflict with it) and Sas invites a new way with her methodology.We talk about how so many business owners (and Sas, too) resisted growth in their business to avoid the return to what they left behind in their corporate careers.As always, Kate and Scott share their takeaways.We laugh. A LOT.  Links mentioned in the episode: Self-Belief SchoolSelf-Belief Coaching AcademyPlease rate and follow!  Every bit helps us as we launch.  Thanks!

    1h 14m
  10. Introducing Less than Likely with Kate Jaeger-Thomas and Scott Robson

    04/17/2022

    Introducing Less than Likely with Kate Jaeger-Thomas and Scott Robson

    Welcome to Less than Likely, a podcast about the honest, behind-the-scenes stories of real entrepreneurs and their less than likely journeys of creating successful businesses. Hosts Kate Jaeger-Thomas and Scott Robson tell their own entrepreneurial stories in this episode, what makes them and their business “less than likely” and reveal some of the areas they find the most challenging in their own businesses.  Where the conversation went: Kate and Scott show up as twins. We introduce the podcast, sharing the kinds of entrepreneurs and conversations we will be welcoming to the show. Kate shares how her unlikely journey into entrepreneurship is deeply linked with her becoming a mother.Kate and Scott reflect on how when growing up - despite having entrepreneurial parents - neither were encouraged to see that as an answer to "what do you want to be when you grow up?"Scott tells his entrepreneurial origin story, where he found himself in a job that he liked, but work that was slowly diminishing the impact he wanted to have in the world. We touch upon the idea that being a business owner can have a part to play in your personal healing journey. We say excited exactly 17 times about who we will have on the podcast, the broad cross-section of industries, models, and personalities to come. Links mentioned in the episode: KJT CoachingThe Curious Life Please rate and follow!  Every bit helps us as we launch.  Thanks!

    50 min
5
out of 5
16 Ratings

About

Welcome to Less Than Likely, a podcast about the honest, behind-the-scenes stories of real entrepreneurs and their less than likely journeys of creating successful businesses.