Kerry Sheppard grew up an entrepreneur and helped grow the family business early in her career. When opportunity knocked to do something different, she found coaching and the rest unfolded from there.    She was raised by a nurse mom and a job hopper dad who eventually started his own business.  She got to see both the corporate and entrepreneurial side of working, but Kerry leaned towards the entrepreneur side.   In college she started in psychology with a business minor; then switched. Eventually, she started working in her dad’s small business.  This gave her a view as an employee in a small business. She took over her territory and worked from her apartment while going to school. A year out of school, she opened a business with her father.  This was much sooner than anticipated. She worked in her business at night and her dad’s business during the day.   As the years progressed, she ended up with 12 cell phone retailers.  The retail stores took a toll on her with the hours. She started looking to something new, and she was introduced to a network marketing company.  She knew this was the future. She decided to go to a Business School for network marketing and hired a coach.  She ended up deciding that she wanted to become a coach. All of the sudden they got an offer and in 10 days all the retail stores were sold. She went to interview with the buyer and knew immediately that was not for her. She knew that it was time to step into her coaching business, and it started! Her background was in sales so her strength was in sales coaching.  She did dabble into the business startup coaching, but there was nowhere to scale the business upward.  She pivoted into more passive income strategies and diversification. She has actually just brought back on a network marketing line. She felt like every month was just a hustle and there was not a lot of freedom in that.  That was the motivation to create residual income and passive income. This was her way to scale instead of building more and more employees and coaches under her.   She watched her friend launch a business with the values she agreed on.  The process of just sharing the product with people, giving them the value, and offering them to take the next step. She just knew watching her that this was the perfect next step to get in. 

CEO Stories 057: Leaving the Hustle Behind

Overnight success and easy entrepreneurship -- no such thing. The CEO Stories podcast exists to help you see how the best in online business ACTUALLY did it (failures and all) and what is bringing them killer results in their business today. You’ll be encouraged with a behind-the-scenes look at the messy parts of business, equipped with practical strategies and tactics, and inspired by a different side to their success stories with your host Kate Boyd -- Virtual CMO + Launch Strategist of Cobblestone Creative Co.

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Growing a business is hard work, and building the right team and processes to become the CEO you were meant to be is no easy task. Laura Brandenburg learned that in corporate and found new challenges in trying to keep the corporate world out of her business and rebuilding balance back into her life and the lives of her team members.  Coming from a corporate background and owning her own company she did not see herself as CEO.  She felt like CEO’s were just very distant. After 10 years she realized that holding the vision and what impact they are making was her job as CEO in her company.  She thinks about what she wants the company culture to look like. To start defining this CEO role, she took on much more marketing and vision while handing off a lot of the day to day aspects of the business.   How to market and grow the team together is a big question she asks herself.   The reality is that she has been the writer, the author, and in front of every video.  They have to think about who does what best to be able to properly delegate the other things.   She got to a point where every month she delegated or eliminated something in her business. Laura is really good at protecting her creative time in the morning. You have to carve out specific planning times.  She does not succeed if she does not have her morning creative time.   Laura has a virtual assistant that is stretched to thin.  They are trying to bring in multiple people to help relieve her.   They are moving into doing more corporate and team clients.  This means more managing of customer relationships. Do you build the team to support the sale and trust that or build the team once the sale has been made? You can plan and plan and plan but until people actually want it, it does not matter. Some of the negative experiences in corporate leads us to have to unpackage those things.   She has organized the business as times to not stress people out like corporate did. It has been a detriment, and she has had to grow from that. Laura has had to do work on herself to grow into the leader that she should be.   Many organizations still do not value business analysis.  Inside the company when people get into the role, thing are very different then what they were explained in school.  There is an undervalue of the true skillset. Her vision is to show why it is important and how valuable a business analyst can be in a business.   On a project, they eliminate waste and make sure they are solving the correct problem.   Investing and training for your business analyst team shows that you value this.  The product on your projects will show their value. It is a very fulfilling cycle. In 5 years, she still sees online training and a very similar structure, just expanded mentoring programs for more on the job work that are largely supported by the instructors.  It starts with a class, but every project is a little different so additional support is very important. Laura would like to travel and keynote to people about mindset. People are held back by their self-belief.  She would like to continue to help other business entrepreneurs. 

CEO Stories 099: Balancing Your Creative Work and Your Business Growth

It’s hard enough to go on vacation as a one-man (or nearly one-man) show, but it’s even harder to prepare for weeks or months away and coming back with less capacity than before. Ashley Olivine shares how she prepared and survived the road to maternity leave.  Ashley focuses on adapting and flowing with life changes.   Her business has to be constantly changing schedules.  To Ashley, this is a positive. She uses a lot of trial and error.  Things work one day but they may not work tomorrow.  She does not have to stick with the old ways. To stay adaptable, she uses brain exercises to keep her from thinking and reacting out of stress.  She constantly thinks about how to propel forward. To know when to change things up, sometimes is very clear and others you have to think outside the box. For example, Ashley is about to have a baby.  In this next season she is going to need to focus on the programs where people are working through on their own and not a lot of one on ones set up. Allow yourself to have the freedom, especially when you have a business and a newborn. Ashley had a big fear that changing things in each season would look unprofessional.  She has actually learned that her clients support her more when she is real and honest.   Change can actually propel you to a better place with your clients.   Our brains for survival are wired to think about the worst case scenario and the risks.  We think: What are the hazards? What could go wrong? How do I protect myself? In these days in the US, our brains do not need to worry about these things.  The worst case scenario is that the business will not work out and we will end up with some business debt. You are not going to die if your business fails. She knows that she is going to be moving overseas so she is trying to plan for this.  In her world now, everything is in her phone. She is not going to be able to have this.  She is turning to funnels, automated things, and getting all of her business off of her phone.  This is actually going to be good for her business because her clients that suffer from insomnia are awake in the middle of the night.  It may actually be good for her to talk with them at that time. Ashley is also using this to set appropriate boundaries about not being glued to her cell phone 24/7.       Adapting for what is better for her can actually benefit the clients too. Ashley suggests making sure you look at the big picture and the strategies are long term sustainable. Systematizing with the emails has been great for her, but everyone needs to step back and see how their transition will change their life and ability.   Visualize what you like, don’t like, and what you want to change.  Paint the picture you want it to look like and structure your business around that.  Make it fit the first time instead of trying to fix things later. Sit in a chair and visualize or write in a journal all of your priorities and how do they fit into the structure of your business.   

CEO Stories 096: Preparing for Maternity Leave as a Solopreneur

Most of us our experts in our businesses, but also we’re usually REALLY bad at taking our own advice. Ashley Olivine found herself in the same position when she let her own physical and mental health drop on the priority list and she shares how she moved it back to a healthy place and stays there.  Ashley’s big fail moment was not following her own advice.   Doctors are their worst patients and entrepreneurs don’t always practice what they preach.   She was getting sick and going to the medical community but it was not getting her anywhere.  She knew something was not right and something was wrong with her. If she had a client with those feelings, she would push them to continue to dig into the problem and listen to their body.   Instead of doing this, she listened to the medical community and thought that she just was not good enough. She was waiting for their validation to start taking care of herself in a better way.  Ashley was trying to serve everybody else and put herself last. She did not give herself enough value.   This ended up going on for over a year.   Not taking care of herself made the business suffer.  Clients could just sense something was wrong. Ashley just could not devote all her effort to the business.   Trying to juggle school, business, motherhood, and everything else was getting to her.  After a doctor’s appointment she was told to just go to the beach instead of driving straight home.  Ashley had a call and she decided to do it! After the call, she had time to enjoy her daughter.  It was a huge turning point that she really could run a business and be a mom at the same time. The people on the phone could hear the rejuvenation in her voice.  They knew she was doing well, and the next day her business took off again!   Conflict keeps us stuck in all of our relationships.   Now she does not feel guilty when she can’t do all of the things.    When Ashley is sick, she lies down and recovers instead of trying to push through with guilt that she isn’t doing enough.   Ashley keeps in mind that taking care of herself is actually best for her clients and her business. You do not have to give up your family for a career or your career for your family.  You can have both. 

CEO Stories 094: Learning to Give Yourself the Rest You Need

Ashley Olivine always had an entrepreneurial brain, but in high school, she suffered a traumatic brain injury that she thought would hold her back for life. But it turned out the very thing that brought her life back to normal would bring her entrepreneurial purpose back to the forefront.  Ashley always had an entrepreneurial brain from boat waxing to babysitting.  From a young age she was into making money on her own. In college, she switched majors a few times.  She ended up with a business degree. She thought she would end up in the corporate world, but it just did not work out. She first transitioned from the corporate world because she did not feel like she had a very big purpose.  She was not happy and she had issues with her voice not being heard. She had an opportunity in the health space that she believed in.  She did not have the qualifications, but she went for it anyways. She ended up getting a chance and being top in her training class. Ashley pursued this on the side and then left her corporate job to go full time.   She went for this job, without meeting the qualifications, because of personal reasons.  She had a traumatic brain injury in high school, and she went through a special insomnia program.  This helped her recreate the neuropathways in her brain. Ashley was then able to go on and lead a normal life.  This program was really special to her after saving her life, so she went for it when they were hiring. When working the two jobs, she was single and had the time to do both.  It was very manageable. She became very unsatisfied in her day job, the opportunity arose to go full time in the health job, and it all just unfolded at the proper time. She started in a doctor’s office doing one on one, in person, face to face structured sessions.  She now has online flexibility because her clients had a lot of trouble getting to her. Going online was very relieving.  She was able to devote more of an open schedule.   She treats her schedule and work ethic as if she is in the office, staying away from distractions. She offers both one on one and do it yourself options for curriculum.  The platform she built helps the technological side more smooth for the customers. Ashley is big on setting expectations from the beginning on what the program is going to entail.  The clientele needs to keep their phones off as if they were in a face to face meeting. When she made the first transition to the health space, she did not have a husband or a family.  After getting a family this transition online was whole lot different. She has also branched out the business from just focusing on insomnia to other issues. Ashley now understands what it is like to have children and other issues that impact their health.  She offers open availability to her clients. Take what life gives you.  Throw out all the stuff you worry about.  Stop resisting. Go for it! Turn your challenges into opportunities.   Her being sick was an opportunity to help other clients.     

CEO Stories 093: Turning Your Challenges into Opportunities

Want to make more sales? Maybe you need multiple salespeople on your team. For Kelly Roach, it’s been invaluable as she built a business both online and offline. She shares her insights on building a solid sales team to increase her client pipeline and her consistent revenue.  The hybrid model of building online and offline is key to Kelly.   Kelly says the biggest problem is that people do not talk to the current customers, talk to their past customers, or touch base with the warm leads that did not buy anything but showed interest. The quickest way to build your business is to talk to the current people that you have.  Build true relationships so that they refer you to another client. Put on the calendar one hour a week for you or your team to follow up with your inner circle for referrals and up sales.   The people who have already paid you are the most likely people to pay you again. Each team member of Kelly’s has a list that they are responsible for reaching out to.  Custom message, tests, emails, calls, or notes are sent weekly. Do things to surprise and excite people.   You need to make the investments in your customers, even before they make the investment in you. Be human.  Be friendly and enjoyable to talk to while adding value wherever you can. People have people in their audience sphere right now.  Use them to help you innovate and create. Just being a friendly, open, human goes a long way these days.  People want to deal with a confident human being that actually cares.     Her team goes every week business to business to bring by marketing material with a food goodie.  They then follow up with these businesses on a regular basis to make the sale. This helps the balance of in person and online clientele both going strong. You have to be both proactive and reactive.  This means having a balance in your portfolio to adapt to change.   They leverage social media every single day by using podcasting and webinars.   The last two programs that she launched she uses a pop up group on facebook for a 5 day challenge.  It took a lot of stress off the team with little barrier of entry. People are done with the automation.  They want to see you, feel you, and touch you.  It makes the sale. Kelly plans to spend a lot of time in the next year on live streaming.   She built her model around virtual coaching.  Lately her team has been closing a lot of in person business sales that she is able to go in and teach face to face.  It is very refreshing. Each team member has linked in accounts that they are to touch base with, the company sends emails weekly, Kelly speaks weekly, each team member is required to get a certain number of referrals each week, podcasts, and livestreams all help keep the business running. Every year she accesses how many new clients came in, what source brought them in, and how much time they spent in each of those areas.   Every week they go over the top 8 areas of client sourcing.  It helps keep everyone focus on all 8 areas and not just one thing at a time. Be out front and build a team.  Rip down the barriers and get in front of the people in your circle. Leverage live streaming, and then a team will help you grow in scale.   

CEO Stories 057: Leaving the Hustle Behind

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