MULTI-MILLIONAIRE Entrepreneur | On Purpose Podcast | Alli Webb | Podcast Summary | The Pod Slice
Transcript
During this segment of the “On Purpose” podcast, Jay Shetty hosts Alli Webb, the prolific entrepreneur and co-founder of Dry Bar, a brand valued at over $100 million. Alli shares her life journey, from her decision to forgo college and move to New York City at just 18, to becoming a stay-at-home mom after getting married. After around five years of staying at home, she felt an itch to do something more and started a mobile blowout service. This was not motivated by finances but more for the need to interact with the adult world and follow her gut feeling to do something fulfilling.
Webb narrates how she took a seemingly simple idea—charging $40 for convenient at-home blowouts—and turned it into a successful mobile blowout business in Los Angeles. The service spread like wildfire as satisfied customers spread the word within their circles. However, the demand eventually outstripped what she could personally offer, sparking the idea for a physical store where her clients could come to her—thus Dry Bar was born.
Alli emphasizes that her path was non-traditional, a reality she is eager to share in order to inspire other aspiring entrepreneurs. She defines entrepreneurship as a journey that is both incredible and challenging, mentioning that she felt like an unlikely success story, positioning herself as an underdog who defied societal expectations.
She argues that not knowing the hardships of entrepreneurship ahead of time can be beneficial, promoting an “ignorance is bliss” mindset while starting a business. With this approach, would-be entrepreneurs can venture into their businesses without feeling too overwhelmed. She also trusts her instincts and encourages others to do the same in order to find their unique paths and personal fulfillment.
In her personal life, Alli acknowledges her struggle balancing love and career, sharing her fears of experiencing a second divorce and her ongoing quest to balance love for a person and her work. She also expresses the challenges and rewards of her entrepreneurial journey in her book “The Messy Truth,” which recounts how she built a multi-million dollar business but almost lost herself in the process. It serves as a testament to her approach to highlight the raw realities behind entrepreneurial success alongside the triumphs.
In this thought-provoking conversation, Alli Webb, founder of Dry Bar, expands on her journey into the entrepreneurial space while emphasizing the significance of incremental growth over massive leaps. She paints a vivid picture of how she nurtured her mobile blowout service, turning it into a successful bricks-and-mortar business. It started with her realizing a growing demand for her services she couldn’t keep up with personally, coupled with her gut feeling to do something that provides personal fulfillment.
She shares her piece of wisdom that instead of pursuing financial gains, entrepreneurs should chase something they genuinely love. Webb never thought of reaping massive financial benefits when she started; rather, she focused on something she enjoyed doing and was good at. Her immense love for her job turned into an everyday joy, a sentiment she wants future entrepreneurs to experience for themselves.
Webb explores the concept of intuition versus delusion during this conversation, implying that intuition stems from the inner feeling of “rightness” about an idea, while delusion might involve ignoring red flags that signal potential pitfalls. She underscores that it’s essential to stay “close in” – paying close attention to the immediate circumstances and how they make one feel. This ability to listen to oneself has become more pronounced for her with age, and she suggests that our intuition becomes clearer when we quiet our minds and truly listen.
In her book, “The Messy Truth,” Webb also speaks about delving deep into oneself and identifying one’s unique skill set. From her perspective, it’s just as critical not to devalue one’s skills simply because they come easily. Instead, acknowledging and maximizing these skills can make a significant impact. Webb highlights the importance of mastering your best skills and applying them to areas of work you’re passionate about, an essential recipe for success in any entrepreneurial journey.
Webb further delves into her personal journey, emphasizing how she found her niche and true passion despite societal and familial expectations. Webb confessed her love for hairstyling was something she initially ignored for many years, primarily due to pressure from her parents who were not supportive of her desire to go to beauty school. However, she was determined about her passion, which she pursued relentlessly. Even Webb’s parents’ disapproval couldn’t deter her, highlighting her innate determination and tenacious spirit to follow her dreams.
Webb shares valuable insights about raising money for new enterprises and confesses the challenges she faced in trying to convince financially-oriented men in suits about the concept of Dry Bar. Despite having to face skepticism and doubt, Webb was firm in her conviction that her business would work. She expressed how she firmly believed in her business model and its scalability, and while external voices did plant doubts, she always trusted her gut and kept going.
Similar to any driven entrepreneur, Webb acknowledges the fear of failure, but diplomatically explains that even if this venture failed, it wouldn’t be the end of the world. Sharing her pragmatic perspective, she implies the importance of not being overly attached to the outcome of the venture. Rather, entrepreneurs should prepare and then take the leap of faith.
Continuing this narrative, Webb opens up about the pervasive phenomenon of ‘imposter syndrome’, turning this generally negative concept on its head, viewing it as an embraceable part of personal growth and progress. Speaking from her own experience, Webb recalls how she used her beginner’s perspective, lack of formal business training, and willingness to adapt, learn, and grow from her mistakes to build Dry Bar from the ground up. This approach echoes her earlier sentiment about ‘staying close in’, focusing on one’s immediate circumstances and learning on-the-go.
Webb highlights the importance of humility in leadership, mentioning how she used to believe she needed to have an answer to every problem as the boss. However, she has since transformed this mindset into one that welcomes and encourages inputs from others, accepting the freedom that comes with acknowledging your lack of knowledge in certain areas.
Alli Webb showcases her wisdom surrounding leadership and the value of feedback in her professional career. She recounts having been open to feedback, seeing it as a gift, and emphasizes that considering criticism from a defensive standpoint only stunts personal and professional growth.
Webb shares a particularly impactful piece of feedback provided by her brother, who pointed out that she was unintentionally intimidating her staff. This feedback shocked her, as she had not perceived herself as such. Instead, she attributed her high-strung nature to her deep passion for her business and the desire for everything to be perfect.
However, this conversation sparked self-reflection and made her realize that she needed to alter her approach. She acknowledged that, despite her intention, her behavior was seen as threatening and affected how her employees interacted with her. To address this, she committed to refining her communication and managing her initial reactions better, thereby fostering a more open and positive environment.
This open, beginner’s mindset has allowed Webb to leverage opinions from those around her meaningfully. She adamantly supports the idea that a diverse perspective makes for better decision-making and a healthier working environment. Webb likens this feedback process to mirrors reflecting back invaluable truths that help her be a better leader.
Webb applies this receptive attitude to her personal life as well, particularly in her relationship with her two sons. She pointed out that her kids provided brutally honest feedback, which she welcomed despite its occasional harshness. Acknowledging the stinging truth in her children’s words, she learned to balance her assertive tendencies and be more patient, allowing them the space they needed.
Addressing the intersection of material success and personal life, Webb opened up about her divorce from her husband, who was also her business partner. She mentioned that her desire for a perfect family image initially delayed the decision to divorce. However, she eventually came to terms with the reality of her deteriorating relationship. Webb admits that this was a significant turning point in her life, as it led her to confront and address the messier truths of her life.
Webb relates how she’s experienced two divorces in her life, and the impact this had on her. While she initially carried feelings of shame and embarrassment over these failed relationships, she came to realize that people grow and change, often in ways that don’t dovetail with their partners.
Echoing this sentiment, her host, Jay Shetty, explained that it’s unreasonable to expect two people to have the same thoughts, dreams, and aspirations every day. As people evolve individually, their relationships must also shift and accommodate these changes. The challenge lies in monitoring whether these changes are pulling the partners apart or drawing them closer together.
Webb reflects that in her first marriage, she neglected her personal life and children to a degree due to her overpowering focus on her business, Drybar. In contrast, in her second relationship, she solely concentrated on love, losing sight of her individuality and pursuits. This led to a severe imbalance in her life.
The conversation then took a turn toward ‘balance,’ with Shetty arguing that it’s mathematically impossible for a person to succeed in every area of their life at the same time, explaining that life unfolds in phases, and it’s essential to openly communicate what you are focusing on during each phase.
Webb shared how during her second marriage, there was an underlying issue that both she and her partner were avoiding. Despite knowing that something was not right, they both feared that addressing it would lead to the end of the relationship.
She stresses the importance of having honest conversations in both personal and professional life, expressing regret about the unaddressed issue in her second marriage. She believes that facing the issue head-on and having an open discussion about it might have changed the course of the relationship, for better or worse.
Her experiences with failed marriages and business endeavors shed light on the importance of balance, understanding individual growth and change, and the essential role of open and honest communication.
The podcast continued with Jay Shetty and Alli Webb discussing how they each maintain their relationships with their partners. Shetty mentioned four check-ins he does with his wife regularly. They discuss daily highlights, weekly or monthly help needs, quarterly relationship direction, and annual goals. Insightfully, Shetty recommended similar self-check-ins to understand personal growth and evolution better because people tend to forget that adults continue to grow and change, much like children.
Webb then brought up the importance of accepting life’s uncertainty, citing Bruce Lee’s daughter’s book entitled “Be Like Water”. She expressed her struggle with unpredictability, desiring neat and tidy outcomes. However, she realized that surrendering to the current of life and recognizing continuous personal growth is vital.
Both Webb and Shetty emphasized the importance of staying on a spiritual or self-awareness path. Webb confessed that she often needs constant reminders not to veer away from her path, especially when life becomes too comfortable or happy.
Shifting focus, Webb openly discussed her divorce experiences. Her first divorce resulted from a lack of emotional intimacy. Following the divorce, Webb experienced a bout of depression, struggling with identity, and rebuilding her life as a single mom. This experience taught her to appreciate the energy taken away from her life post-divorce, which she initially shrugged off, likening it to dealing with a societal death.
Her second divorce was sourced more from heartbreak. She experienced a devastating sense of trauma, defined by her as the intersection of unexpected and overwhelm. However, as she started healing, she appreciated the lessons, growing into a better version of herself ultimately. She urged listeners to remember that it’s okay not to be okay sometimes and stressed that they’ll managed through their struggles, eventually finding healing and growth.
While discussing the nuances of marriage, divorce, and personal growth that Webb went through, she and Shetty unfold a concept about the intersection of an unexpected event and a familiar feeling, which often leads to trauma or triggers traumatic responses. Analyzing this revelation, Webb acknowledges her predilection towards beating herself up due to failed marriages, reflecting skewed self-perception influenced by societal pressures and personal insecurities.
Webb then delves into her fascination with the power of the mind and its potential to change one’s thoughts. However, she acknowledges the necessity of allowing grief to unfold naturally, countering rapid mindset changes. Along these lines, Shetty notes that dealing with grief and loss involves two layers: grieving for the person one loses and grieving for the person one was with them. He also wisely reminds listeners about identity transformation, spotlighted by relationships and personal hardships.
Then the conversation returns to Webb’s two marriages. From her first one, she recalls that she might have rushed into it, fearing loneliness. She identifies the need to have honest, tough conversations about individual needs and potential incompatibilities in a relationship. From her second marriage, she derived that sometimes things won’t work out the way one desires, alluding to the need for acceptance and surrender. This understanding came to a crux when Webb realized her aspirations changed, desiring not just professional satisfaction but also a passionate love life.
Shetty and Webb end this portion of their conversation denouncing the illusion of perfection perpetuated by society, noting it as a significant hindrance to personal growth and healing. They appreciate each other’s willingness to openly discuss their ‘messy truths,’ aiming to help listeners feel seen, heard, and encouraged to embrace their own complex journeys. Using the analogy of a sad movie, Webb elaborates how one can learn to observe personal life as a movie, thus lessening the intensity of suffering during sad phases.
The conversation transitioned into discussing the critical aspects of entrepreneurship, where Shetty pushes Webb to reveal her thoughts in a segment called the ‘Final Five.’ Webb explains the best advice she received as an entrepreneur was emphasizing ‘progress over perfection,’ urging those in similar positions to simply start their journey and figure things out along the way. Rather than waiting for all the pieces to align perfectly, taking this proactive approach can lead to learning from mistakes and moving forward.
Webb moved on to discuss some detrimental advice she had been given. Speaking from her experience, she noted that listening to too many voices can misguide decision-making processes. Admitting it’s important to have valuable and supportive individuals around, she highlighted the perils of asking too many people for their opinion. Webb dished out this advice using Steve Jobs’ example – he didn’t create the iPhone based on people’s needs or expectations; indeed, people didn’t even know they needed it until it existed.
Emphasizing the need for ‘awareness practice,’ Webb stated that entrepreneurs should cultivate mindfulness habits. Reflecting on her routine post-separation, she swapped TV time with quiet time, reading, meditation, and writing. She extended this practice even to bed – choosing a sleep mediation caused her to fall asleep faster and deeper.
Meanwhile, Webb defined her purpose as giving back and being of service. Despite being partly financially motivated, her biggest satisfaction comes from volunteering, mentoring other entrepreneurs, and possible involvement in animal welfare initiatives. Concluding the ‘final five,’ Webb wished for a universal law decreeing kindness to all – a straightforward yet transformative idea, indeed.
Prospects for the show included further dissecting Webb’s book throughout the season. The podcast host and guest concluded their conversation on a positive note, with an affirmation to continue their new-formed friendship.
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