The Art of Management—For One or Many—With Productive Flourishing Founder Charlie Gilkey

The Art of Management—For One or Many—With Productive Flourishing Founder Charlie Gilkey
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The Nitty Gritty:

  • Why to shift from hiring contractors to hiring employees
  • How to keep your team from becoming overcommitted and overwhelmed
  • How to structure time to enhance creativity

This week, my guest is on the Profit. Power. Pursuit. podcast is Productive Flourishing founder, Charlie Gilkey. Charlie is a best-selling author, speaker, blogger, podcaster and business strategist. His website has been visited by nearly 3 million people and his tools, worksheets and planners have been downloaded more than 1 million times. He’s taught thousands of people how to go from idea to done using simple, but powerful approaches that tap into their strengths and genius.

Charlie and I talk about the art of management—whether for one or for many including the shift from contractors to hiring employees, how to keep your team from becoming overcommitted and how to structure time to enhance creativity.

From Contractors to Hiring Employees

I hire and select for people who are versatile, adaptable and like to do multiple things.

— Charlie Gilkey

Although Charlie still has independent contractors on the Productive Flourishing support team, he built a core team of five employees who are all dedicated to achieving the same goal. They all wear many hats and are multifunctional to allow for changes to, and growth of, the business. He found it is harder to build culture with freelancers or contractors. Everyone on the core team who are employees already understands the goals, processes and culture which is sometimes harder with freelancers or contractors who must figure these things out in addition to doing the job they are getting paid to do. As your business grows what you actually need is people who fit your culture, can show up each day to dedicate their time to your business and be flexible.

Control the Overwhelm

If we have to wear 17 different hats, at least know who is wearing which hat.

— Charlie Gilkey

When you have a small, but versatile team of people who “wear 17 different hats,” it’s important to have very clear job descriptions and roles and responsibilities. People are in different lanes of responsibility and different projects that they own. Charlie’s team also uses Asana to schedule regular routines and projects. When people aren’t keeping up with their routines, it’s a sign that they are overcommitted. By knowing what the routines are, when they need to be done and who is doing them, a lot of the meta thinking is not needed. The answers are in the routines. When your team isn’t clear about how things are going to get done, the uncertainty zaps your team’s productivity and morale. Plus, in the last year the team has gotten a lot better about determining the projects they are going to commit to and saying “no” to others.

Structure Time to Enhance Creativity

A lot of creative people don’t recognize how supportive structure and defaults are.

— Charlie Gilkey

A lot of creative people rebel against the very things they need the most. High-performing creative people inevitably have these really well thought-out structures and containers to do their creative work. Productive Flourishing is to the point that the processes and structure are set, so the team can use their creativity on the work and not use it to figure out what the work should be and how it will get done.

Tune into the entire podcast to learn more from my discussion with Charlie including how businesses and professionals make things harder and how he articulates his intuitive synthesis to his team. You can learn more about Charlie Gilkey and download his free planners for creative people from his website.

And, listen to the Productive Flourishing podcast on Apple Podcasts, Google Play, or wherever you listen to this podcast!

The Secret to Small Business Longevity with Career Coach Michelle Ward

The Secret to Small Business Longevity with Career Coach Michelle Ward

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The Nitty Gritty:

  • How to plan and pivot out of a crappy job
  • How a brand evolves and “grows up” over the life a business
  • Why entrepreneurship allows the flexibility to adjust your business when you face a negative or positive situation out of nowhere

My guest on the Profit. Power. Pursuit podcast this week is Michelle Ward, founder and career coach of When I Grow Up, a firm dedicated to helping creative women get out of their “soul-sucking jobs and discover—and launch!—their authentic, fulfilling businesses.” After 20 years of preparing for and pursuing her dream of being an actress, she suddenly realized it was no longer the life she wanted to lead and decided to get a “real job.” We talk about her own transition to discover her own dream career, how the When I Grow Up brand has evolved and how her business became her relief and release after being diagnosed with cancer.

Plan and pivot out of a soul-sucking job

The devil you know is oftentimes better than the devil you don’t.

– Michelle Ward

Michelle started to get beaten down by the business of show business, and decided that even though she had spent her life up to that point preparing for a career as an actress, it was no longer what she wanted to be when she “grew up.” But, she ultimately didn’t know WHAT she wanted to be and she didn’t want to settle for anything less than something she was passionate about. After a lot of soul searching and help from a career change class, she realized being an entrepreneur really fit everything she wanted for herself.

She became the coach that she couldn’t find. But, as Michelle shares in our interview, it took several years of planning and working a “grown-up” job as an executive assistant so she could pay her bills and get her training before she pivoted to a full-time career coach.

Evolution of the When I Grow Up brand

Overwhelmingly, my people told me that they were attracted to me and stayed around because they clicked with the name.

– Michelle Ward

Since Michelle’s name is so common, it never crossed her mind to use her name as her business name. After some deliberation, she settled on the name When I Grow Up because every time she would share it with others, they would laugh and “get it.”

There have been three different logo/brand shifts as the brand has grown up over the years. Michelle has worked with the same designer since the beginning of her business and during our conversation she shares how the look and feel of her brand has shifted. She’s really happy with where the brand is right now and Michelle believes that the caliber of the clients she attracts is a really big nod to the business name, brand, how she shows up online and how authentic she is.

Each year, Michelle creates an infographic to illustrate her business by the numbers that offers a fascinating look into her revenue streams and business expenses.

Adjust your business when necessary

Whether it’s something negative or positive out of nowhere the same rules can apply.

– Michelle Ward

Everybody responds differently to the trials and tribulations of life when being an entrepreneur, but the promise of entrepreneurship is that you have the ability to adjust your business in a way that works for your life circumstances. Michelle shares how she weathered the storms in her business including two different bouts with “boob cancer” in 2011 and 2015. At the forefront of her approach was honesty and transparency with her clients. Michelle explains how she adjusted her business during her surgery and treatment based on what she still wanted to do that made her feel good, what she thought she could manage and how she could alter the expectations to show up at a certain time and avoid feeling guilty if she wasn’t up to it.

I invite you to tune in to listen to the entire podcast where you will hear all the nitty-gritty details from this long-time entrepreneur and learn about a great opportunity to join Michelle at the Pivot Assembly, a virtual event with amazing career change experts, including yours truly, to learn about how to pivot out of your crappy job into a more traditional job or entrepreneurial work.

Each week you can learn from the experiences of successful entrepreneurs to build your own business. Subscribe to the Profit. Power. Pursuit. podcast on iTunes to get the nitty-gritty details about how these professionals built brands and teams and are living out their dreams as an entrepreneur.

Fueling Your Business With Live Events with Tradeshow Bootcamp founder Katie Hunt

Fueling Your Business With Live Events with Tradeshow Bootcamp founder Katie Hunt
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The Nitty Gritty:

  • Why live events are where it’s at
  • How the sales and promotion cycle of a live event is different than other sales cycles
  • Why it’s important to add to your team to allow you to focus on the tasks in your wheelhouse

We dig into the nitty-gritty details of live events in this week’s episode of the Profit. Power. Pursuit. podcast with my guest Katie Hunt, founder of Tradeshow Bootcamp, a business dedicated to educating and supporting creative entrepreneurs and small businesses. Katie also hosts the Proof to Product podcast. She takes a lot of pride in the events her team creates, and on that podcast she shares a lot of wisdom about what it takes to create events that offer attendees a great experience for learning and having fun, too!

Live Events are Where It’s At

Introverts of Profit. Power. Pursuit., go to live events. It’s completely worth it.

— Tara Gentile

What was to become the live event known as Paper Camp began in 2011 as a teleconference, and the first in-person Paper Camp Conference happened in 2012 once Katie knew there was a demand for this type of curriculum. Katie wanted to build a strong community where people were not just learning something, but they were connecting with others and building strong relationships. She knew that would be much more impactful at live events. Events are a really powerful tool, and although they aren’t right for everyone’s business model, they are hugely successful in helping Katie build the community that she sought to create.

Organization, Sales and Promotion of a Live Event

There’s a lot more that goes into their decision making {to attend an event} than ‘can I afford this and do I want to go.’

— Katie Hunt

Katie and her team work 6 to 8 months in advance to prepare for their next live event. She suggests if you’re doing a live event for the first time, send a survey to your audience to determine the best time of year for them to attend a live event. In the podcast, Katie walks through the steps her team takes to organize a live event, but keeping it simple and streamlined for her attendees and speakers is always paramount.

Since a live event is a higher-level program and higher expense for attendees, it’s important to start the sales and promotion process early since there is a schedule you have to maintain and people need the time to prepare to be away from their families and businesses. As soon as they close registration on one Paper Camp, they begin sales for the next one; however, there are promotional spikes in a three-month period where most of the sales happen. Through the course of the sales cycle, Katie and her team are nurturing their audience through case studies, alumni stories and more to help potential attendees see how their life would change if they attended the event and give them a taste of what they will learn, who they will be engaged with and to highlight the speakers they will interact with and learn from.

Event Teams

You can grow your team organically and in small batches.

— Katie Hunt

Katie has a small, but mighty team of virtual independent contractors, several who are Boot Camp alumni, that take care of the event details so Katie is free to work on the content and higher-level stuff that’s in her wheelhouse. Hiring people to do the work that needs to get done strengthened the content that is offered at the events.

I hope you listen to the entire episode to hear more about Katie’s team, how she manages cash flow when she has fairly large expenses to cover, why she believes in paying herself consistently and how she has turned some of her live events into online courses.

If you liked what you heard on this episode, I invite you to subscribe to the Profit. Power. Pursuit. podcast on iTunes today! Every week I talk to small business owners who share some of the secrets to their success as they build their businesses.

Creating Systems for Efficiency & Productivity with Indie Shopography founder Emily Thompson

Creating Systems for Efficiency & Productivity with Indie Shopography founder Emily Thompson

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The Nitty Gritty:

  • How purchasing a tanning salon when she was 18 set Emily on a track for entrepreneurship
  • Why extremely detailed process management will help you feel more productive
  • How Emily balances the demands of running two businesses

This week, my guest on the Profit. Power. Pursuit. podcast is Emily Thompson, founder of Indie Shopography and co-host of Being Boss, a podcast for creative entrepreneurs who want to up their game. At Indie Shopography, Emily helps creatives build and run online businesses from the design and development of their business websites to marketing and education products. Emily and I talk about the time she bought a tanning salon at the ripe age of 18, why her extremely detailed process management helps her feel more productive and how she balances running two businesses.

Lessons from owning a tanning salon

I remember thinking this would not be my last relationship with business.

– Emily Thompson

When Emily was 18 she worked at a tanning salon one night a week in exchange for getting to use the tanning beds herself. Even though she had never taken a business course and was young, she could tell the business was in trouble. Then, thanks to a combination of moxie and mettle she made a call to the owner and ended up buying the salon and owned her first business at age 18. During our conversation, Emily shares insights about this opportunity and although it was a relatively short period of time, she credits it with giving her the bug to be a business owner. Today, she is very intentional about building a business that really allows her to do work that works for her.

Detailed {often painstaking} to-do lists for optimum productivity

My trick for myself is breaking down those tasks so minutely that sometimes I can check off 5 things in 5 minutes because I really broke them down that small.

– Emily Thompson

Whether Emily is designing a website or developing a new educational product, her process is very much the same. She outlines her entire process in the podcast and emphasizes the power of her detailed to-do lists that break down tasks into bite-size chunks. Once she has that very detailed plan, she schedules it out by using Asana. Even though her to-do list may seem super overwhelming for every project, she knows that tackling each of those individual tasks—that are small and manageable—she will ultimately get to the end of it. When those to-dos are marked off, the end result is a new product or website has been created.

Secrets to juggling two businesses

I don’t have to wear too many hats. They’re the same hats, just different colors.

– Emily Thompson

In the podcast, Emily shares her experiences and thoughts about how to juggle being the boss for two different businesses. She loves that she doesn’t have to put all of her energy into one thing, and that makes having more than one business appealing to her. The two businesses give her enough structure to not pigeon-hole herself creatively into one creative endeavor. She and her partner at Being Boss put together a very detailed marketing calendar annually so that they have a clear view of what’s happening in all three of their businesses so nothing gets lost.

In the full episode, we talk more about Emily’s passion for Asana, the structure of her team, as well as what’s on the horizon for both of her businesses, plus a book launch next spring! I hope you’ll tune in to receive all her valuable insight.

Learn from today’s most innovative and inspiring entrepreneurs every week by subscribing to the Profit. Power. Pursuit. podcast on iTunes when you want to know how small business owners really manage their time, develop outstanding products, build their teams and get new customers.

Why Marketing Campaigns Fail with CoCommercial Founder Tara Gentile and Media Strategist Brigitte Lyons

Why Marketing Campaigns Fail with CoCommercial Founder Tara Gentile and Media Strategist Brigitte Lyons
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The Nitty Gritty:

  • What four big-picture reasons cause marketing campaigns to fail
  • Why it’s important to have a willingness to explore the reasons for failure
  • What are some of the common tactical points of failure

On this week’s episode on the Profit. Power. Pursuit. podcast I tackle the question, “Why Marketing Campaigns Fail” with Brigitte Lyons, founder of B, a marketing and PR agency that works primarily with small organizations to hone their marketing message and market positioning. We discuss some of the main challenges business owners in this new economy face every time they go out and market a new product or service. There are so many predictable reasons why marketing campaigns fail and we examine these roadblocks in this discussion so you can avoid them in the future.

Four Big-Picture Reasons that Cause Marketing Campaigns to Fail

The marketing should be baked into the product that you’ve developed and that requires you starting with your audience.

– Tara Gentile

So often, businesses only want to focus on their successes and never want to look at the reasons something fails. In our opinion, this is a missed opportunity. All the answers you need about your marketing tactics should be answered in your marketing strategy. Too often business owners question if they are posting on social media enough (or too much) or if they should amp up their content marketing. This focus on tactical efforts is always a clear signal that a business hasn’t thought through the strategy of a marketing campaign or really put a road map into place.

The most common reasons that Brigitte and I see for marketing campaigns to fail include:

  1. You put your needs ahead of the needs of your audience.
  2. You don’t set crystal-clear expectations around what success is and don’t run the numbers around what that will take.
  3. You save marketing for last (but it should be first).
  4. You don’t use your failures as an amazing learning opportunity.

Be Willing to Explore the Reasons for Failure

Sometimes it requires a little creative thinking to match your needs with theirs.

– Brigitte Lyons

When you start feeling like you need to convince your customers or they are very excited about your message yet have a very big BUT that holds them back from purchasing, these are red flags that you have a problem. It might be a marketing, communication or messaging problem; perhaps you have a position, product or format problem. Whatever it is, you need to reach out to your customers, preferably in person or on the phone to uncover what they don’t like. It is important to get curious to explore what the underlying problem really is.

Common Tactical Points of Failure

Listen to the full podcast to learn the six common tactical points of failure for a marketing campaign that include relying on social media to sell your products or services and your follow-up (or not following up) and to hear all of our takeaways for why marketing campaigns fail and how you can avoid those issues.

Our discussion is a great intro to a class I will be doing on CreativeLive, “Create a Marketing Plan to Grow Your Standout Business.” If you tune in on August 1 and 2 you can watch and learn for free. RSVP today!

You can also find me {most} Mondays (and sometimes Brigitte joins in, too) on my CoCommercial Crowdcast channel where I talk about the ins and outs of growing a small company you love.

Disrupting a Very Old Market with Cora Co-Founder Molly Hayward

Disrupting a Very Old Market with Cora Co-Founder Molly Hayward
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The Nitty Gritty:

  • When there is a need and an opportunity for a better product, you should not be deterred by the magnitude of the industry you’re going up against
  • How to go about entering an old market with a new product
  • Why strong customer service, including a free trial program, and flexibility with the subscription system is crucial to Cora’s success

Molly Hayward, co-founder of Cora, a premium organic tampon company that provides a month’s supply of pads to women in need for every month’s supply of tampons purchased, is my guest this week on the Profit. Power. Pursuit podcast. During our inspiring conversation, we talk about the genesis of Cora, disrupting the traditional market of women’s period products and how exemplary customer service has been crucial to their success. There is so much value in this conversation, I hope you tune in!

Disrupting a Traditional Market

I was aware, but undeterred by the magnitude of the industry that was I was going up against.

— Molly Hayward

The concept of creating a premium organic tampon for women that would also help women in need around the world better manage their periods, first came to Molly when she was on a humanitarian trip to Kenya with a non-profit organization. On the trip, she noticed that some of the girls would go missing from school and when she inquired about their whereabouts she found out they stayed home when they had their periods because they didn’t have products to manage it in public. It was a lightbulb moment.

Molly starting thinking about other companies in other industries such as Toms or Warby Parker that were successful with the one-for-one model and felt there was an opportunity to connect the purchases women in America make every month and supply women in need at the same time. Sustainability and organic products were also important to Molly, but she realized that there was no one in this space that was offering products that met her standards. She set out to design a better-for-you and better-designed product than what was offered by the traditional companies in the industry who were fearful of change.

I was so convinced that there was an opportunity here and a need for a better product experience for both women here and women in developing countries so I forged ahead and started.

— Molly Hayward

What It Takes to Change a Longstanding Industry

And so as I began to dig into the industry and look at what it would take to offer a better product to women here.

— Molly Hayward

When Molly came back home, she started research. She began to dig into the industry to look at what it would take to offer a better product to women here. First, she realized there was not a brand that represented all the values of most modern women today. Once she determined that she wanted to offer an organic product, she had to find a manufacturing facility that could do what they wanted. That translated into more research time on Google and factory visits. Molly and her team floated the idea of the one-for-one model to a lot of different people and questioned if people would accept it or just roll their eyes. Had it been overdone? Would the market react to it?

Molly’s instinct was this product category, maybe more than any other type of product category, would hit a personal chord with women. We have all had the experience by our own error of not having a product when we needed it. And, it’s a crisis. Imagine going through that every single month and have it derail your life.

Customer Onboarding and Exemplary Customer Service

Giving women options and the ability to customize their orders was a big piece of what was integrated into our model within the subscription.

— Molly Hayward

Since most women have treated their periods reactively, the Cora team built flexibility into their subscription model so that women could alter the products they receive without any weird friction or penalties as they learn more about how much and what types of products they need or as their bodies change. They also implemented a free trial program that has been crucial for getting women comfortable with testing out a new product. Perhaps the most important element underlying it all is Cora’s exemplary customer service where customers can email, text or call in to get support.

Listen to the Full Episode

There is so much more to experience with the full episode, including the reasons why the design of the product and packaging was super important to the Cora team, how customers are responding favorably to Cora’s social mission and what’s next for the business.

I invite you to join me every week to hear the honest truth directly from entrepreneurs who are in the trenches building businesses. You learn the nitty-gritty details about HOW these entrepreneurs develop their business ideas, build teams, manage their time and more. By subscribing on iTunes  you will never miss a single episode.