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In episode #65 of My 2.0 Podcast, guest Dolly Oberoi, CEO at C2TI, shares her scaling story at C2 Technologies. Dolly is a true pioneer in online training, sim & modeling, and thought-leader, innovator, and entrepreneur. Through her work at C2TI, she reshaped traditional chalkboards to electronic learning environments and developed transformative enterprise-wide training and talent management solutions. Dolly talks about the genesis of entrepreneurship as she worked for her entrepreneurial mother in India, in search to bring learning technologies to connect children and learning across the world. She also talks about the initial challenges of entrepreneurship, especially as a female business owner. And how these challenges change as the business evolves over time.

In episode #64 of My 2.0 Podcast, guest Kim Kross, COO At Elevate K-12, shares her scaling story at Elevate-12, where they are on a mission to make zip code free teaching available to all students, irrespective of where they live.  Kim talks about the mission of Elevate K-12, including the opportunities and challenges that the pandemic provided to their stakeholders. While they have achieved tremendous scale, she is forthcoming in the dichotomy of a company’s ability to scale exponentially while most humans scale linearly.  how her decisoning framework has changed over the years, incorporating evolution over time with the agility a rapidly scaling company requires.

In episode #63 of My 2.0 Podcast, guest Carolyn Trabuco, CFO At Inclusively, Co-founder/Board Member at Azul, shares her scaling story with Azul, the airline she co-founded with David Neelman, the founder of JetBlue.  Carolyn talks about her background as a Art History major who found a job as a phone rep and eventually through grit and determination, moved on as an equity analyst. She shares her scaling stories at Azul, where she was invaluable with her outsider perspective. She talks about linear v/s bath scaling, about shaping ESG initiatives, and about potentially seeking a path back to art history. 

I launched My 2.0 podcast just a little over a year ago; to create a platform through which women could share their experiences of successful career transitions so that we normalize career changes. In reflecting on these profound stories of career changes, I saw close parallels with how we scale ourselves to transition careers, and how we scale businesses. So it seems like a natural transition of this storytelling journey to Women Who Scale; where you will hear from women on how they scale themselves; be it to transition careers and/or to scale their business. Because in the end, the only constant in life is change.  Please stay tuned for new episodes next week!

In episode #61 of My 2.0 Archives, guest Bosky Mukherjee, Founder at PMDojo & Spark To Substance, shares her transition from a career in corporate to entrepreneurship.  Bosky’s life has been a lifelong series of transitions, as she moved across geographies, through various types and sizes of company. The only constants were her love for the product and her desire to always be growing. Motherhood changed her in new and unforeseen ways, as she struggled with the extreme physical challenges with her newborn son. She learned to not settle, to always ask for more from herself and from others around us. But in that process, while she continued to scale the heights of her corporate career, she suppressed the toll that brought on her emotional well-being. And so when her body finally collapsed with burnout, it provided her the tipping point to assess what she really wanted from both her professional and personal lives. 

In episode #60 of My 2.0 Archives, guest Justine Evirs, host, entrepreneur and writer, shares her transition from a career in the Military to becoming an Entrepreneur.  Justine walks us through her many transitions starting in her childhood, through to getting into the Military, to becoming a military spouse and finally transitioning out into a higher education, non profit serving the Military and veterans eventually finding her calling in entrepreneurship. She’s never lived in a house for more than three years, and is a first generation college student. And is very open with her struggle with alcohol, including hitting rock bottom three years ago.  Resources:  Stanford GSB ProgramProtecting Courage Podcast Courage To CreateThe Paradigm Switch

In episode #59 of My 2.0 Archives, guest Maxine Cunningham, CEO of Pick My Brain, shares her transition from a career in investment banking to entrepreneurship.  Maxine described her journey of training as an economist, her experiences in the Investment Banking world, then as an environmental economist finally being inspired by the Airbnb founders to create a platform that allows for gifting, buying and selling knowledge in what she believes to be the future of the information/knowledge economy.   Resources:  Pick My BrainAirbnb 

In episode #58 of My 2.0 Archives, guest Linda Wenger, Strategy Consultant at Urbaneer, shares her transition from a career in programming to entrepreneurship. Linda’s first job was at a company called NCR for client support. She went back to graduate school to get her MBA and transitioned to the technical side. She then moved to a consulting company at MCI as a product manager.  Early on in her career, Linda had decided she was going to transition every 2 years to be able to learn and grow most.   Soon after, she had her first child and fully transitioned to motherhood. And that was not an easy transition. It was hard coming from a pretty exciting and changing life to transition into something that was a little bit more sedentary. But as we do as moms, we grow into our roles and we learn every day. About four years later, she had her second child and threw herself into volunteering with the schools, running auctions and fundraisers, to be active with networking. Linda thought transitioning into and out of motherhood was very difficult. Starting with postpartum depression, losing the sense of freedom, workplace achievements, being physically exhausted all the time. Transitioning back into the workforce was equally challenging. She fought guilt about not being there for the kids. And on missing out being in the industry for 8 years.  And in 2007, she transitioned into helping her husband with his new business in the association industry, in SaaS. Not only did she not know anything about the industry, much less about the work. The world of startups was new and different. And yet, one of the best experiences of her life. It caused her to grow up very quickly.  She went back to school again, to Georgetown, for a leadership program. And is now consulting with a company in the construction industry, one in which she has no experience! But is using her strong skills in finance and strategy to advise them. She also thinks transitioning is the most challenging, and it’s hard going from stable and known to a new place, one you may not know much about. She also finds that the more mature she gets, the harder it is for her to transition. Because the younger generation is hungry to get things done. And we start questioning our ability to keep up with them, and the learning. But the right answer is for us to continue to have the courage to transition no matter our age. Her advice to her pre-transition self is to be aware of how easy it is to get stuck in the waiting place. And that there is no such thing as failure, just early attempts at success. And that women are the strongest people on the planet. And always learning is beneficial. 

In episode #21 of My 2.0 Archives, guest Dorie Clark, strategy consultant, executive coach, and keynote speaker, shares her transition from a career as a journalist to an entrepreneur.  Dorie thought she was going to be an academic but got turned down for all doctoral programs. Her Plan B was to become a journalist, and she ended up getting laid off after about a year on the job.Eventually she found her way into working in politics, running a nonprofit for two years realized that she wanted to run her own business. And moved on to having her own consulting and executive coaching business. On the topic of feeling stuck, Dorie felt she didn’t have the luxury of being stuck, and that always needed to figure something out and keep pushing. She decided she was going to exhaust every possible resource, call everyone she knew to hustle and network my way into whatever the next thing is. Dorie’s advice to her pre-transition self is contained in her book Reinventing You. She interviewed about 50 other professionals who had made career transitions to create a guide that people could use to feel more in control of what can often feel like an out of control process. Her advice was for us to reinvent ourselves in small ways on an ongoing basis and keep ourselves current. The less likely we are to be faced with a situation where we're static for five years or 10 years.  When asked why she wrote Entrepreneurial You, Dorie said it was her attempt to figure out ways to scale her business in developing simultaneous and adjacent streams of businesses.  When asked what it means to have a brand, Dorie answered it needs to start with who we are and what we are able to do, and articulate it to the market. And that when we transition to a different career, we have to be the captain of our narration.  Dorie also talked about her new book coming in September ‘The Long Game. How to be a long-term thinker in a short term world’. Over the last 5 years, she has met a lot of great people and built up a longitudinal perspective and pattern recognition around observations that I've noticed in terms of very smart, very talented professionals in the stressors they face, that come in the way of long term growth. That we don’t know how long it takes to become a successful recognized expert. So this is her attempt to light this dark, long and opaque path.  When asked how we could future proof our careers, Dorie shared that the one thing we do know is that whatever position we're in, we want to be as protected and secure as we possibly can be. So that if disruption is coming down the pike, we are able to pivot with enough time. On the power of identifying and defending ourselves against our vulnerabilities, Dorie shared that it’s very easy to focus on what you lack, but if we do that, we are accepting other people's frames. The truth is while we are lacking certain things, we are developing new skills all the time.  Dorie also shared the free self-assessment that is tied in the book Revinting You at www.dorieclark.com/reinvent.  Resources Home - Dorie Clark - Official WebsiteReinventing You: Define Your Brand, Imagine Your Future: ClarkEntrepreneurial You: Monetize Your Expertise ... - Amazon.comThe Long Game: How to Be a Long-Term Thinker in a Short-Term ...

In episode #20 of My 2.0 Archives, guest Sarah Brown, Senior Director Sales Enablement at Health Carousel, shares her transition from a career in counselling to entrepreneurship.  Sarah’s journey started with a Master's in counselling. She worked in juvenile corrections with a superintendent who had been there for 20 years and was very experienced. He had a very robust intervention program that she learnt a lot from. But she was burnt out and was looking to make more money. He suggested that she apply for a training manager position. She first thought she shouldn’t, since she didn’t have the skills. But he convinced her how she had already been doing this job, and so when she got the job, she loved it, and excelled in training and development. Fast forward, she now works in a healthcare system running their leadership programs including coaching their teams and executives.  Sarah always knew that she loved variety. She also got the confidence to move into a consulting role outside the organization for 15 years. And decided to open up a blow dry bar in 2015. She invested money, time, heartache, into this and two and a half years later, she closed it and it was devastating.  She had really attached personal value, her self worth to the success of the business. And she was embarrassed that people will attribute her to the failed business. At that time, she decided that she was going to separate her self-worth from what she did professionally. When I asked her for tips on how to solve this problem, she said to start with being aware of the issue. And to take the time to notice triggers, to pause, to reflect on what drives us to feel positive or negative. She also feels that the universe has a great way of redirecting us when we are not in the right space.  Sarah’s biggest challenges during her transitions were the self-limiting beliefs in her head. And the irony that no one cared. If anything, people were envious of her ability to pivot and rebrand herself.  Sarah’s most recent endeavor is 0.0 Living, which helps people reset their relationship with alcohol. And that could look like containment, abstinence or anything else in between. This comes from a personal struggle Sarah had with alcohol and one she saw manifesting with a lot of people during the pandemic.  She created the Failing Forward podcast so she could touch people with inspiring stories of failures that people learn from, and change from. It started with being local for Cincinatians but just this January, Sarah took the podcast global, telling and sharing stories all around the world.  In debunking transition myths, Sarah thinks that we need to understand the value of our transferable skills, and articulate them into the new/next job. And to understand the importance of EQ and not just rely on IQ.  The advice she would give your pre-transition self is to bloom where you're planted, stay planted as long as you can. And move to a new location when you’re ready.  Sarah then asked me a question about what gifts the podcast has given me. To which I said it connected me to many women I learned from, that I would not have met otherwise. And it teaches me to be a more empathic and curious listener.   Resources:  Failing Forward Podcast

In episode #55 of My 2.0 Archives, guest Bea Wray, Author and Keynote Speaker, shares her transition from a career as an entrepreneur to an author.  She grew up always knowing that she’d be a psychology major and a psychology researcher. And she went to college for psychology and even did an honors thesis and was on a path to do research and hopefully eventually go to graduate school. But while she presented her thesis, expecting to fail, given it wasn’t statistically conclusive, she was shocked to receive the highest honors. Her own reaction to that was to find another career. And so she went into business, starting and leading many successful companies. When I asked her how she compared her career with her father’s 30 year career at Ford, she said she has worked with entrepreneurs and startups. She understands imperfections and chaos and problem solving in a way which is different from people working in large corporations.  Bea’s advice to her pre-transition self is for people to always be open and true to themselves. And to be aware of your surroundings and what you want out of life and use all the incredible opportunities that come our way.  Some of the transition myths Bea would like to debunk are that career transitions cannot be done and that the next thing may not be better. She talks about our career being a three-legged stool; each leg representing industry, position and geography. And that we should never try to change all at once. When I asked what led Bea to write the book, she mentioned that after selling the company, she took six years off spending time with her family. And when she went back to the workplace, she felt intimidated with very low confidence. And she realized she kept receiving thanks and compliments for helping people and when she reflected about her innate skills, she realized all her skills from business schools were honed by her kids. It included empathy, communication and negotiation. And that was making a difference.And one thing led to another and she started writing about it and I published a little article in entrepreneur.com. So at some point she knew a book would come out. As she lost her confidence and was trying to figure out the next point in her career, she asks us to never let not having confidence get in our way. And if there is something we want to try or do, we owe it to ourselves to try. She offers her advice on negotiation skills using the BATNA principal they use at HBS; the best alternative to a negotiated agreement. She explains how she has never looked for just one job, but multiple ones at a time.  Her thoughts on whether children should be allowed to fail were that being an entrepreneur, she understands the importance of establishing a culture of failure so it allows for risk taking. Which is similar to our career transitions. Taking that to parenting, we want our children to not have to be perfect, and to accept failure. Resources. What an MBA taught me..but my kids made me learn

In episode #17 of My 2.0 Archives, guest Judy Robinett, Founder of Crack The Funding Code, shares her career transition from social work to a power connector.   Judy calls her career transitions ‘one mistake after another’. She went to college for a Physcology degree and became a social worker after. She transitioned to getting her masters in Economics and started figuring out that she was good at business. Working in Fortune 500, she felt nausea on Sunday nights thinking about going to work on Mondays. After more explorations and reflections, Judy decided to start her own business running a franchise restaurant for 8 years. She maintains that the important thing is to do the hard work. We will hit a wall, but will also figure out a way over it, under it, around it, since there’s always a way. After selling the restaurant, a friend asked for advice for a biotech company that was broke and in litigation. After she helped them with their challenges, she was asked to be a CEO. She struggled internally with questioning her own competence in being the CEO of a public company but worked through that challenge to successfully raise money and turned it into a success. She thinks that the next level will bring the next devil and as Tony Robbins says, a Golaitah shows up every time but it’s up to us - whether we’re going to get a sling and a rock or run away.  Additional questions for Judy. What helps us get through current challenges and be ready for the next one? In Judy's opinion, asking people for help, and knowing where to find the right people in the right rooms is what helps us get through current challenges and be ready for the next one. She also believes in the right mentors and to always be learning. We should be asking people the three golden questions; How can we help them, what other ideas they have for us and who else they think we can talk to.  What causes us to break out of our comfort zone?We should think through all our preconceived notions and assumptions of difficulties. To solicit as much help as we can, to ask for training when we need it. And to understand that if we don’t get out of our comfort zone, we’re stuck.  Her advice to pre transition self.To kick fear to the curb. To avail all opportunities and use all the information and ideas we have and are surrounded with. To get into the right rooms with the right people to ask the right questions.  What led her to write ‘How to be a power connector’? Judy wanted to write a book about funding businesses. When her agent discovered the types of people she knew, she asked Judy to write a book on networking. And Judy wrote this book to help people like her, shy and unsure. To turn each stumbling block into a stepping stone that makes us stronger, and puts steel up her spine. How can women use wisdom through the book in their career transitions?This book will help us evaluate our current network, and build it out, including helping us find people smarter than ourselves and in different walks of life.  What led you to write ‘Crack the funding code’?Judy didn’t want to write another book. But the more people she talked to, she realized how critical and pervasive the problem of funding for startups was. And so through this book, she intends to provide founders the wisdom and resources to show them the right rooms with the right people that can help them with their funding problem. How do we make sure we get more women to the starting line of entrepreneurship, and find funding for their businesses?Judy’s advice is to take baby steps, networking one person at a time. And to leverage resources like the