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NotOnTheHighStreet.com Founder: Rapid Success Lead To My Darkest Days - Holly Tucker | E92
46 segments available
This weeks episode entitled 'NotOnTheHighStreet Founder: How Rapid Success Lead To My Darkest Days - Holly Tucker' topics: 0:00 Intro 2:15 Your early years 16:37 Losing orientation in your life 22:13 The Not On The High Street story 34:28 Optimism in business 41:48 Hiring for a business 50:41 Losing myself within the business 55:30 Leaving not on the high street and rediscovering myself 01:08:30 Helping people create a “good-life” business 01:19:47 Do what you love, love what you do Holly: https://www.instagram.com/hollytucker/ https://holly.co/ Holly’s book: https://www.amazon.co.uk/dp/B088TF94G6/ref=dp-kindle-redirect?_encoding=UTF8&btkr=1 Listen on: Apple podcast - https://podcasts.apple.com/gb/podcast/the-diary-of-a-ceo-by-steven-bartlett/id1291423644 Spotify - https://open.spotify.com/show/7iQXmUT7XGuZSzAMjoNWlX FOLLOW ► Instagram: https://www.instagram.com/steven/ Twitter: https://twitter.com/SteveBartlettSC Linkedin: https://www.linkedin.com/in/steven-bartlett-56986834/ Sponsors: https://uk.huel.com/ https://myenergi.com/?utm_source=steven_bartlett&utm_medium=referral&utm_campaign=podcast
Segments Timeline
The Early Struggles of Holly Tucker
Holly Tucker shares her journey from being diagnosed with a brain tumor in her early twenties to becoming the founder of Not On The High Street. She reflects on the challenges she faced as a woman in tech and the initial skepticism from investors. This segment highlights her determination to change the retail landscape despite the odds stacked against her.
"early twenties i was diagnosed with a brain tumor that was the first knock down holly tucker ex-ceo and founder of not on the high street holly's story is mind-blowing we go and pitch the idea of not ..."
Holly Hurricane: A Drive for Success
Holly discusses her childhood nickname 'Holly Hurricane' and her eagerness to grow up and work. From taking on jobs at a young age to interning at a prestigious advertising agency, she emphasizes her strong work ethic and the influence of her family's entrepreneurial spirit. This segment showcases her relentless pursuit of success and independence.
"i hope nobody's listening but if you are then please keep this to yourself [Music] i always start in the same place in this podcast because i think it provides the greatest amount of context on a pers..."
Lessons from Heartbreak and Health Challenges
In her early twenties, Holly faced significant personal challenges, including a difficult marriage and a brain tumor diagnosis. She reflects on the turmoil of this period and the lessons learned about identity and resilience. This segment captures the emotional weight of her experiences and the importance of self-discovery during tough times.
"so that has been a constant in my life i studied art uh at a level and i created this huge sculpture that they had never had someone do before called tom dick and harry and they actually cast it in br..."
Reinventing Myself: From Adversity to Creativity
Holly shares how she navigated her health issues and divorce by returning to her creative roots. She discusses her journey into freelance work and the birth of her idea for vegetable wreaths, which led her to create a local Christmas fair. This segment highlights her ability to turn adversity into opportunity through creativity and entrepreneurship.
"interesting lesson which is be careful to be in a hurry all the time just because you want it and you can get it doesn't mean it's right and so we found ourselves as natural human beings developing in..."
Building Opportunities: The Birth of a Fair
Holly explains her initiative to create the first Chiswick Christmas fair to sell her vegetable wreaths. She emphasizes her belief in creating opportunities where none exist and her passion for building. This segment illustrates her entrepreneurial spirit and determination to make her ideas a reality, showcasing her proactive approach to challenges.
"to find out who i am again because when you pull your identity into something else that's not yourself or or it becomes your identity i think we all do that in relationships sometimes you know that yo..."
Embracing the Unknown
In this segment, Holly reflects on the risks and uncertainties of starting her own events business. She emphasizes her love for small businesses and the joy of curating unique stalls. Holly discusses the challenges she faced while organizing events, including unpredictable weather, and how these experiences deepened her appreciation for entrepreneurship.
"i don't just because it doesn't exist doesn't even bother me it's actually just part of the fun of building i'm i'm i love building i love it about the risk um well what risk because um you know what ..."
Navigating Life Changes
Holly Tucker opens up about significant life changes, including the end of her marriage, and how they can lead to a loss of direction. She shares her insights on the emotional journey of rediscovering oneself after such changes and offers advice for those feeling unanchored in their lives. This segment resonates with anyone facing personal upheaval.
"because i was on my own putting on these events it was you know pouring with rain one day you can't control the weather you can't control the football being changed you can't do anything but what it d..."
Finding Your Brand Heart
Holly introduces the concept of a 'brand heart'—the core essence of a business that should reflect the founder's identity. She discusses her own journey of self-discovery and the importance of understanding what drives her as an entrepreneur. This segment provides valuable insights for business owners looking to align their personal values with their brand.
"lasted for you and what advice you'd give to someone who because i experienced it a little bit when i like left my business or actually the first time i experienced it was when someone made me a reall..."
The Role of Support Systems
In this segment, Holly emphasizes the importance of surrounding oneself with supportive people during challenging times. She shares how her partner played a crucial role in her journey, providing encouragement and perspective. This discussion highlights the value of community and relationships in personal and professional growth.
"of you so i think what i did was i went back to so what makes holly exist what makes holly alive and through that process which was about a year um and my second one which will come to probably you kn..."
Patience in the Entrepreneurial Journey
Holly reflects on her initial lack of patience as an entrepreneur and how her perspective has changed over time. She discusses the importance of listening and being open to the journey rather than rushing towards a destination. This segment offers a thoughtful take on the evolution of ambition and patience in business.
"you know what that is and so i was lucky to have that but that brand heart like the who is holly just cutting it up into five pieces and say okay if there were five things i've got to concentrate on t..."
The Naivety of Starting Up
Holly shares her experience of launching Not On The High Street without any technical expertise. She discusses the beauty of naivety in entrepreneurship and how it can lead to innovative solutions. This segment captures the essence of starting a business with passion and creativity, despite lacking formal experience.
"and then what you need to do like experiment do something yeah just well actually that's not what i did for not on the high street but it is what we've done for holly and co because um that was the yo..."
Building a Marketplace from Scratch
Holly recounts the early days of creating Not On The High Street, highlighting the challenges of building a marketplace without prior tech experience. She discusses the initial funding, the launch day chaos, and the unexpected hurdles they faced. This segment illustrates the resilience and determination required to bring a vision to life.
"um yeah and um and i'm enjoying that that's what i'm really enjoying so i've got a we've got to go through this um this uh not in the high street story because i when i was reading um about your journ..."
The Spirit of Entrepreneurship
In this segment, Holly draws parallels between entrepreneurship and parenting, emphasizing the fierce dedication required to nurture a business. She reflects on the challenges of being a founder and the emotional investment involved in building something meaningful. This discussion resonates with anyone who has poured their heart into their work.
"thought we could create a solution and all we needed to do was take all those small businesses that were under my town hall roof and just put them on this thing called the internet and then wouldn't i..."
The Launch of Not On The High Street
Holly Tucker shares the challenges faced during the launch of Not On The High Street, including the lack of tech experience and the struggle to secure funding. Despite launching without a checkout feature, they creatively pivoted and gained significant media attention, showcasing the resilience and determination of the founders.
"the curious the discover the small businesses and things but i had a three-month-old baby that wasn't going to stop me and so we went on this journey to build it and as i said you know we tried to bui..."
Facing Financial Struggles
Holly discusses the financial difficulties encountered shortly after launching Not On The High Street. She recounts the experience of fundraising in a male-dominated VC landscape, the personal sacrifices made, and the dark days when the business seemed on the brink of failure, yet remained operational due to unexpected holiday sales.
"functionality and so we launched we called it a press preview and we just pivoted and we were uh on something called daily candy which was huge at the time we were on the daily mail front cover all th..."
The Turning Point
In this segment, Holly reflects on a pivotal moment when they secured their first round of investment after a challenging pitch. She shares the emotional rollercoaster of nearly losing everything and the relief that came with finding an investor who believed in their vision, marking a significant turning point for Not On The High Street.
"street was definitely on its last breath but the issue was it was working you know it hadn't been working up until that point we used to have a bell that you would ring when there was a checkout of 30..."
Unwavering Optimism
Holly emphasizes the importance of optimism in entrepreneurship, sharing her belief that despite financial struggles, she never doubted the success of Not On The High Street. She draws parallels between being a parent and a business founder, highlighting the resilience required to overcome challenges and the unwavering belief in their mission.
"but that was how close we were um but you know we definitely turned right that meant we got our first vc fantastic and then um you know we started building not on high street and it was growing very v..."
The Power of Gratitude
As Holly reflects on her journey, she discusses how gratitude has become a driving force in her life and business. She contrasts her earlier survival mode with a newfound appreciation for her time and the impact she can have, emphasizing the importance of serving oneself while serving others.
"what is your favorite flavor of heel jack berry my favorite flavor of fuel is banana berry used to be my favorite flavor and i saw someone tweet the other day they said um because puel is now in tesco..."
Understanding Your Own Power
In this segment, Holly explores the evolution of her understanding of personal power and its role in her entrepreneurial journey. She shares insights on how her optimism not only fuels her but also inspires those around her, creating an emotionally charged and creative work environment at Not On The High Street.
"all work out optimism because you've also because because you've employed a lot of people seeing the opposite that sense of like catastrophe you know that catastrophizing oh no we're a [ __ ] you know..."
The Power of Optimism
In this segment, Holly discusses how her optimism has a positive impact on those around her. She shares her experiences at Not On The High Street, where the creative and emotional atmosphere was palpable. Holly connects her personal power to her ability to uplift others, showcasing the significance of a positive mindset in business.
"behind me there's a little sand timer somewhere on there there's usually a sound timer i don't know it seems to walk around but because i wrote about it in my book at such length people started buying..."
Building a Supportive Team
Holly recounts the early days of Not On The High Street, emphasizing the importance of hiring passionate individuals over those with extensive experience. She describes the energy and commitment needed during the startup phase, illustrating how a small, dedicated team can drive rapid growth and innovation.
"and i can see the effects and i can see you know what we brought up and not in the high street was full of it you know i used to have people come in to the office um from other businesses that we woul..."
Navigating Rapid Growth
Holly shares the challenges of managing rapid growth at Not On The High Street, detailing the complexities of serving both customers and small businesses. She reflects on the importance of coaching partners to keep pace with growth, highlighting the dual responsibility of a marketplace leader.
"out to other people and help them there's an irony in that that you're talking about whipping up a storm and your nickname's hurricane holly yeah actually i've never even said that before and so yes i..."
Curating Quality Over Quantity
In this segment, Holly discusses the philosophy of curating quality products and businesses at Not On The High Street. She explains the decision to turn away many applicants to maintain brand integrity, emphasizing the long-term benefits of prioritizing quality over immediate financial gain.
"um we need energy and we need commitment and we need you not to have a high salary that's the that's that moment in time and so that was what it was and you know we were growing at 2 000 we were tryin..."
The Evolution of Hiring Practices
Holly reflects on her evolving approach to hiring as Not On The High Street grew. She contrasts the initial need for energetic 'soldiers' with the later requirement for skilled professionals, illustrating the challenges of transitioning from a startup mentality to a more structured organization.
"you talk there about hiring and that flipping hiring process at the start which i know very well and i i've joked about on this podcast before like walking into pride and the guy selling the bags was ..."
The Importance of People in Business
Holly emphasizes the critical role of people in business success. She shares insights from her experiences, highlighting the need for strong relationships and personal connections within her team. This segment underscores the value of investing in team development and the impact of leadership on company culture.
"street it was the soldiers you needed the energy and then you get into the next stage don't you where actually those people by very nature can't stay with the business because now you need skill and t..."
The Challenge of Scaling
In this segment, Holly discusses the difficulties of scaling Not On The High Street while maintaining its core values. She reflects on the tension between operational demands and the creative spirit that initially fueled the business, illustrating the challenges faced by rapidly growing companies.
"dealing with their personal side that's dealing with their professional skills that's dealing with their whole self um and that is something i'm fascinated by and i think i'm potentially going to buil..."
Finding Balance in Business
Holly shares her journey of balancing her love for the business with the operational demands of running a large organization. She discusses the importance of staying connected to her passion and the realization that her role needed to evolve as the company grew.
"we always used to say you know we've got our marketplace hat on one day so that is about trading the site and understanding what customers need and then we've got our retail hat on which is the brand ..."
The Role of the Founder
Holly reflects on the unique role of a founder in a business. She discusses the irreplaceable energy and vision that founders bring, emphasizing that their presence is crucial for maintaining the company's spirit. This segment highlights the challenges founders face as their businesses grow and change.
"we were you know still growing so incredibly quickly um so it was a difficult moment to try and balance that state of growth and tech issues and operational issues and funny enough hr issues when you ..."
Rediscovering Passion in Work
In this closing segment, Holly discusses the importance of doing what you love and loving what you do. She reflects on her journey and the moments that led her to reassess her role within the business, emphasizing the need for personal fulfillment in professional life.
"without you and was there a moment where you realized that you'd have to take a different role within the business yeah i suppose it got to that point where um 200 people five vcs i was chairwoman and..."
The Weight of Responsibility
Holly discusses the heavy burden of responsibility she felt as the main breadwinner and leader of Not On The High Street. She explains how the pressure to support her family and the small businesses relying on her success contributed to her struggles. This segment underscores the emotional complexities of entrepreneurship and the impact on personal relationships.
"looked today you know i was in the tube dress with the high heels on double spanx on i was a she man you know i needed to be that person i was brought up remember i was 28 when i started i was i was b..."
Navigating Dark Days
Holly opens up about her darkest days as an entrepreneur, describing feelings of depression and grief after stepping away from her business. She likens the experience to a mother leaving her child, emphasizing the emotional turmoil that comes with such a significant life change. This segment highlights the need for open conversations about mental health in the entrepreneurial community.
"holly how could i smile or laugh i you know i i found myself becoming a different version of me um one of the lines at holland co is bringing colour to grey and i think i was turning grey did your par..."
Rebuilding After Loss
In this segment, Holly recounts her journey of rediscovery after leaving Not On The High Street. She shares how she surrounded herself with supportive people and began to rebuild her identity. This process involved shedding the pressures of her past and embracing a new, authentic version of herself, which is vital for anyone facing similar challenges.
"and so that has just been difficult you know you know the downs are very down dark dark days when you're running out of money you've got to raise again but the business is going amazingly you have no ..."
Creating a New Business Identity
Holly discusses her vision for Holly & Co, aiming to redefine business as a tool for happiness and creativity. She emphasizes the importance of helping dreamers become doers and creating a supportive environment for small businesses. This segment encapsulates her mission to inspire others and foster a community where entrepreneurship can thrive without sacrificing personal well-being.
"um but it was difficult you know i i couldn't go to events with small businesses i would you know break down i would have to leave i i couldn't see people that i knew i i couldn't meet socially with p..."
Empowering Dreamers and Doers
In this segment, Holly discusses her mission to empower entrepreneurs through her business philosophy of 'dream, dabble, do.' She emphasizes the need for a shift in how business is perceived, advocating for a more supportive and nurturing approach that allows small businesses to thrive without the pressure of traditional business models. Holly's vision is to create a community where creativity and personal fulfillment are prioritized.
"normally it's done in a certain way in a 2d way in a greater way and my plight was to help the dreamers we have a phrase dream dabble do at holly and co i want to help the dreamers become doers and i ..."
Redefining Success in Business
Holly Tucker challenges the conventional definitions of success in business, advocating for a 'good life business' model that balances personal fulfillment with professional ambition. She encourages entrepreneurs to envision their future and prioritize mental health, family, and creativity over traditional metrics of success like wealth and growth. This segment highlights the importance of aligning business goals with personal values.
"quick one i've recently made a purchase i've bought myself a tesla cyber track it's not here yet they're still not to be delivered and the reason i decided to do that i sold my range rover sport and i..."
Creating a Sustainable Business Culture
Holly discusses the need for a cultural shift in how businesses operate, moving away from a focus on competition and profit towards sustainability and long-term growth. She reflects on her own experiences with corporate pressures and the importance of fostering a supportive environment for employees. This segment emphasizes the value of purpose-driven business practices that prioritize well-being and community impact.
"really you know i'm of service i care about people enormously you know if i feel emotional when i talk about it um i want them to have the best life that they can have and i i really would live in gra..."
The Future of Entrepreneurship
In this insightful segment, Holly Tucker shares her vision for the future of entrepreneurship, encouraging founders to embrace their unique journeys and redefine their narratives. She emphasizes the importance of looking ahead and understanding the long-term impact of their businesses on their lives and communities. Holly's message is one of hope and empowerment, inspiring entrepreneurs to create meaningful change.
"so that is where you know i can see myself at 90 here but i do ask people have you looked at the future because you by looking at the future understanding that last point you can work backwards becaus..."
Lessons from the Journey
Holly reflects on her journey as an entrepreneur, sharing valuable lessons learned from her experiences with Not On The High Street and her current endeavors. She discusses the importance of understanding one's purpose and the impact of business decisions on personal and professional lives. This segment serves as a reminder of the resilience required in entrepreneurship and the potential for growth through challenges.
"then we try and shift the company towards a direction where we viewed it as like an infinite game where um there isn't a scoreboard and we're trying to create a sustainable life for ourselves and our ..."
The Struggle for Control
Holly Tucker reflects on her experience as CEO of Not On The High Street, discussing the challenges of maintaining control in a corporate environment dominated by profit-driven motives. She shares her realization that her vision for the company was stifled, leading to her decision to resign. This segment highlights the conflict between a founder's ideals and the realities of corporate governance.
"i was still the ceo but a lot of it's lip service when you don't really have control right they want they need to keep you happy because you have a lot of influence over a lot of things um but i could..."
Lessons from Battle Scars
In this segment, Holly discusses the valuable lessons learned from her experiences at Not On The High Street. She expresses excitement about future ventures, emphasizing the importance of using past challenges to build a 'good life' company. This reflection underscores the resilience required to navigate the entrepreneurial landscape.
"i no longer had that control because starting at 21 giving up that control you can't get it back you can't and now you you have got the war scars you've got the battle scars and then what's so fascina..."
The Zeitgeist of Entrepreneurship
Holly Tucker talks about the current entrepreneurial climate, emphasizing the rise of the freelance economy and the importance of mental health. She connects her journey with the broader societal shifts, positioning her new venture, Holly & Co, as a response to the needs of aspiring entrepreneurs. This segment captures the essence of adapting business models to align with contemporary values.
"i remember i saw someone on a competitor on linkedin the other day just like they had like um they'd paid to take us our name on um seo oh yes yeah yeah you're just like oh you were really looking for..."
Creating a Community Through Writing
Holly shares her journey of writing during the pandemic, including the creation of her book and the daily Instagram live sessions aimed at supporting her community. She reflects on the challenges of writing as a dyslexic and the joy of connecting with her audience through her words. This segment highlights the power of community and storytelling in entrepreneurship.
"so um you know when we're all looking at you know the freelance economy when we're all looking at the changes remember not in the high street was built when the high street was declining holly and co ..."
The Birth of a Bestseller
In this segment, Holly discusses the rewarding experience of publishing her book, describing the emotional journey from writing to launch. She emphasizes the importance of creating a book that resonates with her audience and reflects the values of small businesses. This narrative illustrates the intersection of personal passion and professional achievement.
"couldn't and remember she could rewrite the english dictionary so it was probably the wrong person but right person at the time um i didn't write until four years ago when i started my instagram accou..."
Coloring the Business Narrative
Holly Tucker explains her unique approach to business writing, focusing on creating a visually engaging and accessible book for entrepreneurs. She discusses the significance of making business literature relatable and enjoyable, aiming to inspire small business owners. This segment highlights the importance of creativity in business communication.
"bringing color to gray being passionate your energy you don't have to be great at the p l you have to be great at being you and we'll figure all the rest out at another stage um that you are the found..."
A Journey of Gratitude
Holly reflects on her journey as an entrepreneur and author, expressing gratitude for the support she received from her community. She shares her hopes for the future and the impact her work can have on others. This segment encapsulates the themes of purpose, community, and the fulfillment that comes from helping others.
"it's a color book which was funny because business books normally aren't color but of course it had to be color and it's um yeah sunday times bestseller and i'm super proud of it and i hope that now w..."
Empowering Future Generations
In the closing segment, Holly and Steven discuss the importance of sharing experiences and lessons learned to empower others in their entrepreneurial journeys. Holly emphasizes the need for more voices in the business world that advocate for purpose and authenticity. This conversation serves as a call to action for aspiring entrepreneurs to pursue their passions.
"my life that i can't believe i get to be this lucky and i i imagine because the same with my my book did you did you realize it would be that rewarding because the effort to create it is oh it's a lot..."