Advanced Freelancing

“Wisdom is sometimes wrapped in an ugly experience.”

Despite knowing what to do, a great many would-be entrepreneurs never take the steps to get started because they are afraid of failure. But what if you could reframe the way you think about failure, and see it not just as an opportunity, but maybe even a necessity?

Today’s guest takes grit to another level, and if setbacks in your business have tempted you to quit, his story will inspire you to play the long game and view mistakes as opportunities for growth. Damion Lupo is a serial entrepreneur, having started 30-plus businesses. His latest venture is Total Control Financial, an Austin-based FinTech that seeks to disrupt Wall Street and empower individuals to take control of their own financial future. He is also the author of five books on finance, investments, and personal growth.

Damion has a history of bold moves, getting his start in real estate by purchasing a rental house with his VISA. Over the next five years, he grew the business to include 150 houses in seven states. He took a $20M hit in 2008, but used the lessons from that epic failure to reinvent himself – and write a book about the road back, Reinvented Life. Today, Damion is a consultant and coach who appears regularly on podcasts and radio shows centered around finances and personal development. Listen in as he shares his personal philosophy of 10X thinking, advice regarding retirement planning, and strategies to help you view setbacks with gratitude.

Key Takeaways

Damion’s advice about going all-in

• Stay in motion and you won’t have time for the fear
• Quit you ‘day job’ when you realize you’re stretched too thin
• Trust that the universe will give you signs when it’s time

Why it’s important to play the ‘long game’

• A business takes time to grow
• Plant the seeds by sharing who you are
• Then adopt a willingness to let things germinate

Damion’s 10X thinking

• Say no to being satisfied with 10% growth
• Ask yourself, ‘How can I make this year 10 times bigger?’
• Surround yourself with people who will help catapult you into a bigger space
• Remember that exponential growth makes you 10 times more impactful

The significance of reviewing big picture goals quarterly

• Understand the numbers and assess your progress regularly
• Don’t waste nine months going the wrong way
• ‘Go where the puck is going’ by anticipating changes

How Damion frames failure

• Our mistakes are not us
• Wisdom is sometimes wrapped in an ugly experience
• View mistakes with gratitude (that’s how you grow)
• Failure allows you to reinvent yourself

Damion’s advice on writing books

• Open up a channel by committing to write 20 words
• Allot a specific amount of dedicated time
• Consider hiring someone to hold you accountable

Damion’s tips for retirement planning

• Do something today
• Build the confidence to make your own decisions

How to identify a professional financial advisor

• Weed out the ‘salespeople’
• Find out if they have created wealth themselves via what they’re selling

The benefits of the eQRP as a retirement vehicle

• Gives you control of your investments
• Allows you to contribute $50,000/year
• Empowers consumers

Damion’s first steps to retirement savings

• Educate yourself
• Play Cashflow to understand how you interact with money, finance, and investments

Resources

Grit: The Power of Passion and Perseverance by Angela Duckworth

The ONE Thing: The Surprisingly Simple Truth Behind Extraordinary Results by Gary Keller with Jay Papasan

CASHFLOW Board Game

CASHFLOW App

Connect with Damion Lupo

Total Control Financial Website

Facebook

Twitter

LinkedIn

Damion’s Books

There is much societal pressure on women to be everything to everyone – the perfect mother, the perfect wife, and the perfect business owner. And many female entrepreneurs profess to have struck that perfect balance between self-care and running a business. But today’s guest is here to share her struggle with the chaos that is her life and assure you that it’s okay not to be perfect.

Krystina Dubrule is the CEO and Founder of Du North Designs, Ltd., a family-oriented fashion and apparel business based in McLennan, Alberta. A social worker by trade, Krystina was laid off just before returning from maternity leave after having her third child. Inspired to start her own business, she began crafting hand-sewn clothing and tutus at her kitchen table and then offering her designs at a local market, but quickly realized that this wasn’t a feasible business plan with three small children in the house. Plan B was to place a wholesale order and host home parties with friends and family, and soon she was getting requests from people she didn’t know – as far as 300km away!

Under Krystina’s guidance, Du North has grown into a network of 3,000-plus distributors in the US and Canada, and the company garners over $1M in sales annually. Balancing the needs of her family with the demands of an online business is a test of her abilities, but Krystina has learned to embrace the chaos and incorporate laughter and fun into the life she has built. Listen in as she shares her strategy for picking the right battles, the truth about work-life balance, and how to make hiring decisions when it’s time to reach out for help.

Key Takeaways

Krystina’s keys to juggling family and business

• Let some things go
• Think long-term by asking, “What are my kids going to remember?”
• Be okay with having a happy family
• Don’t ask too much of yourself

Why it’s important to be honest about the challenge of balancing self-care and business

• Demonstrates that it’s okay not to be perfect
• People won’t like your brand any less
• Painting an unrealistic picture may discourage others

Krystina’s tip for staying organized

• Reach out for help on tasks that are not your strength
• Hire staff to share the journey with you

Krystina’s hiring guidelines

• Hire for personality rather than skill
• Hire slowly, but fire quickly
• It’s easier to teach tasks than culture
• Consider whether employee aligns with your mission

Connect with Krystina Dubrule

Du North Designs Website

Facebook

 Twitter

Instagram

Entrepreneurship is a roller coaster ride, with extreme highs and lows. So how do you keep yourself motivated during the rough times? Today’s guests are honest in sharing the despair they have faced as well as the successes – and that was just this week! They are prepared to teach you how to be a creative hustler – embracing the process, increasing your bounce back rate, and living at the intersection of creativity and business.

Steven Picanza and Melissa Rautenberg are the husband-wife team behind The Creative Hustler, a lifestyle brand for creative entrepreneurs, as well as the brand strategy firm Latin & Code. Steven brings his talents as a brand architect, business strategist and creative entrepreneur to these endeavors, as he works to connect people, products, and organizations with their core audience.

The yin to his yang, Melissa has the tactical skills to bring Steven’s vision to life. With an expertise in inbound marketing, SEO, and PPC, her no bullshit approach has built meaningful campaigns across a variety of industries. Today they explain the unifying principles of creative hustlers and how they create balance in their lives. Listen and learn how to shift your mindset to accept that ‘the obstacle is the way.’

Key Takeaways

How ‘The Creative Hustler’ originated

• Steven coined the phrase at a talk in 2011
• Debuted ‘manifesto’ at conference in London last summer
• Brainstormed expansion of idea on plane ride home
• Focus on living at the intersection of creativity and business

The unifying principles of creative hustlers

• There is opportunity everywhere
• We can use each other’s strengths in an ecosystem rather than an ‘egosystem’

Why entrepreneurs have a social responsibility to share the possibilities available in gig economy

The greatest challenges faced by creative hustlers

• Motivation to continue after failure
• Determination to bounce back

How to avoid highlight reel syndrome

• Don’t compare yourself to another’s perfect post
• Remember that everyone is presenting their best selves on social

The importance of mindset

• Necessary component of long-term strategy
• Helps you learn to love the process and see the bad as opportunity

How Melissa and Steven decide if a client is a good fit

• Look for people who ‘get it’
• Core values must match
• Client believes in their own product
• Wants to better themselves and their brand

How Melissa and Steven work together

• Steven plays part of orchestrator
• Melissa’s role is tactical, realizing the vision
• Together, their strengths offer clients a 360° view

How Melissa and Steven stay driven

• ‘Success is the only option’
• Surround selves with inspiring people

How Melissa and Steven create balance

• There is no personal and business life, there’s just life
• Stop and go on a hike or cook dinner
• Enjoy what’s around you in order to recharge

Melissa and Steven’s advice for aspiring entrepreneurs

• Conquer your tiny corner of the internet
• No one will do it for you, but others will want to help once you start
• Serve others and be of value, without expecting something in return
• Fall in love with the process

Resources

The Obstacle is the Way: The Timeless Art of Turning Trials into Triumph by Ryan Holiday

Connect with Melissa & Steven

Creative Hustler Website

Facebook

Instagram

Steven on Twitter

Melissa on Twitter

If you’re an aspiring entrepreneur who juggles multiple responsibilities, you know how difficult it can be to carve out the time each day to work on your business. And if your other responsibilities include being a mom, the struggle is even more real. With all the advice out there urging you to schedule the same time each day to move your business forward, what do you do when your days are too unpredictable to create a consistent timetable?

Jewel Eliese is a self-taught creative fiction writer and the mother of two ‘perfect little goofballs.’ She began Write Away, Mommy as a personal blog, a space where she could share her life as well as her fiction. But it didn’t take her long to realize that she wasn’t really a fan of writing about herself. Over time, the blog evolved into a community where women can get inspired to be better writers and mothers.

Beyond the blog, Jewel serves as the first reader for Grimdark Magazine, and she is currently working on a collaboration with Haley Darling to self-publish a collection of short stories. Today Jewel shares her struggle to gain traffic on her site, how she made use of Google to learn the craft, and how she finds the time to write with two kids at home. Listen in and learn how to deal with ‘mom guilt’ and make writing a part of family time!

Key Takeaways

Jewel’s secrets to becoming a better writer

• Just sit down and write
• Allow others to read your work and offer feedback
• Keep learning
• Employ Google

How to overcome the fear of critique

• Remember that it’s more fun to work with others
• View feedback as a way to make your work better

Jewel’s advice for shifting from writing practice to publishing your work

• It will never be perfect, but you have to get it out there
• Submit and forget

Jewel’s tips for time management as a mom

• Work during naps, scheduled activities, and after your kids go to bed
• Give yourself a daily word count to realize (e.g.: 500 words)

How Jewel incorporates writing into her family life

• Getting her kids involved in the process
• Encouraging her son to contribute a story to the blog each month

Jewel’s suggestions for alleviating ‘mom guilt’

• Live in the moment
• Accept that life is messy and imperfect

Jewel’s ‘ninja’ writing guidelines

• Write by hand in pen to avoid editing
• Don’t take yourself too seriously
• Embrace the fact that first drafts will be terrible

Resources

The Write Practice

Jon Morrow on SmartBlogger

Jeff Goins’ Website

Grimdark Magazine

Connect with Jewel Eliese

Website

Facebook Group

Twitter

Pinterest

We all suffer from insecurities, at times. But when you’re an aspiring entrepreneur, a crisis of confidence may stop you from building a successful business. What if you had a coach with a great capacity for compassion who would provide encouragement when you needed it? A coach who would inspire you to “do it anyway” when you were feeling unsure? Who would hold you accountable?

Shawn Quintero teaches faith-based entrepreneurs how to create online wealth through blogging, social media, and digital marketing. Through his coaching practice, Shawn seeks to help Christian entrepreneurs create deep, meaningful impact on the world and live a lifestyle of complete freedom. He understands how to overcome self-doubt because he’s lived it. Enduring a childhood filled with abuse and bullying, he struggled with depression and suicidal thoughts. But he was inspired by a history teacher who saw his potential, and Shawn began to overcome his insecurities by growing an online network and surrounding himself with positive influences through the church.

Shawn was ready to start his coaching business, but he was self-aware enough to know that he lacked business skills. In order to gain access to the information he needed – without paying the $2,000 application fee – Shawn volunteered to help out with the Lean Startup Conference in San Francisco, and soon he was honing his business acumen and making connections with big names in entrepreneurship. Now Shawn himself is a sought-after speaker and author of the book Online Wealth for the Christian Entrepreneur. Prepare to be motivated as Shawn walks you through his approach to acquiring new clients by providing insane amounts of value up front. Listen and learn strategies to hold yourself accountable and inspire action!

Key Takeaways

Shawn’s strategies for growing your client base

• Build your community and demonstrate value up front
• Hone your skills
• Create extraordinary content that displays your expertise

Shawn’s approach to securing testimonials

• Do your best work, even if it’s for free
• Ask clients to post their greatest insight and next steps

Why entrepreneurs often live an ‘unbalanced life’

• Must be willing to sacrifice to reach goals
• You can’t build a thriving business in an hour per day

Shawn’s best advice for new online business owners

• Get offline and talk to real people
• Find out what your target audience is missing and how you can be the solution
• Surround yourself with people who will help keep you accountable

Resources

Lean Startup Co.

Digital Marketer

Social Media Examiner Conference

Udemy

Connect with Shawn Quintero

Website

Tony Robbins once said that we are thrust into action out of inspiration or desperation. And sometimes it’s a little bit of both! Entrepreneurship can be overwhelming, and it isn’t always as easy to stay driven day after day – especially when the end goal seems so far away. Today’s guest shares his story of working through those challenges and developing the grit to continue. 

Winston Henderson is the Chief Visionaire at 5 Years 2 Mastery, an enterprise that seeks to equip and empower others to overcome the limiting beliefs that are holding them back as they work toward their goals, creating the life they’ve always wanted. He was introduced to entrepreneurship by his cousin at the age of 18. After several failed attempts to establish various businesses, Winston studied IT at university – and hated it. But the blessing in disguise was that he also discovered a love of marketing and a renewed interest in business. At 24, Winston spent a year and a half working a traditional job in sales before starting his own home-based hot beverage business.

Though Winston’s venture was doing well enough that he could quit his full-time job, he struggled to develop the necessary discipline to run a successful business on his own. As things fell apart and Winston entered a state of depression, he took a look at his options: He could either go back to a full-time job, or he could dig in and make it work. The birth of his daughter in 2011 motivated him to choose the latter, and Winston has built a business that serves ten countries and brings in a monthly revenue of $130,000.

Inspired to share his systems and help others reach their full potential, Winston has expanded his work, adding Digital and Content Marketing Strategist and Break-Through and Consistency Mentor to his job title. Listen in as he explains how consistent daily activities lead to big wins and how ‘celebrating the process’ keeps you moving forward as you grow into your most powerful self!

Key Takeaways

The challenges of entrepreneurship

• Mental and emotional discipline
• ‘Dig in and make it work’

How Winston shifted his mindset to acquire the necessary discipline

• Desperation for financial independence
• Strong, emotionally compelling reason to push through the challenges
• Pain of regret stronger than pain of developing discipline

How Winston selected the products he promotes

• Saw a demand/need
• Capitalized on service aligned with that demand

Winston’s advice for building a lucrative business

• Consistency
• Start small
• Visualize the end goal
• Focus on daily activities
• Refuel by celebrating the process

Winston’s secrets to success

• Faith
• Figure out what’s holding you back
• Develop your communication skills

Connect with Winston Henderson

Website

With the rise of new online marketing channels, entrepreneurs have the opportunity to connect with potential clients through various audio and video platforms. But what if you hate the sound of your own voice? Or you just don’t have the confidence to really connect with an audience? The voice is a powerful tool, one that entrepreneurs can use to command attention and share their stories with the world.

Tracy Goodwin is the owner of Captivate the Room, a coaching business that teaches clients how to connect their message with their passion – and make an impact with their voice. Her unique approach, the psychology of the voice, allows clients to unravel their voice story and frees them from the barriers that are preventing them from connecting with an audience. Tracy is an expert in voice technique, and she has trained actors, speakers, entrepreneurs, business executives, leaders, and podcasters from all over the world – helping them step into their voice power and speak their truth.

Tracy graduated from Baylor University with a BA in Theatre and went on to earn a Master’s in Creative Drama from Texas State. She worked for many years as a professional actor and director but kept running from her true purpose as a voice coach because she couldn’t get past her own story. Tracy grew up in a family where she was not allowed to speak, so she just couldn’t see herself as an expert – despite repeated opportunities to coach voice. When she was put in charge of the voice program at a conservatory, she could no longer deny her gift. Today she shares that gift with you, explaining her coaching process and how she connects with clients. Listen in and let Tracy help you manage your time, capitalize on social networks, and make an impact with your message!

Key Takeaways

Why many are terrified to speak their truth

• Link to past trauma (i.e.: abusive/narcissistic parents, teachers)
• Your ‘voice story’ shapes your abilities

How Tracy’s clients know they need coaching

• Lack of confidence
• Dislike the sound of their voice
• Know they don’t captivate the audience

Tracy’s coaching process

• Obtain audio/video of the client prior to coaching session
• Listen to identify the issues
• Understand the client’s ‘voice story’
• Tackle the biggest problems first
• Lay in a new layer of muscle memory

Tracy’s timeline for achieving results

• Utilize techniques and exercises that accelerate progress
• ‘Flip the foundation’ in one month
• Encourage continued practice for sustainable change

How Tracy’s clients are able to improve so quickly

• As they see results, the confidence is transformative
• They are inspired to continue as they build on positive results

Tracy’s tips for marketing yourself online

• Capitalize via visibility on social networks
• As tech evolves, keep learning
• Ask yourself, “Who are my people? Where are they? How can I serve them?”

Tracy’s suggestions re: time management

• Take on tasks that are in your ‘zone of genius’
• Outsource duties that are laborious
• Consider investing in an assistant

What makes Tracy the best voice coach in the business

• She rolls in the psychology of the voice
• Her ability to teach technique and alter muscle memory through drills

Tracy’s advice to aspiring entrepreneurs

• Start before you are ready
• Don’t wait until everything is perfect
• Do your research and develop a plan
• Prepare to learn from your mistakes

Resources

Post Planner

Connect with Tracy Goodwin

Website 

One of the greatest challenges new freelancers face is that of securing those first few clients. What if there was a marketplace where you could advertise your expertise to professionals who are looking for someone with your skill set?

John Connor is the Founder and CEO of HelpWith.co, a community where people connect and exchange skills via one-on-one learning sessions. The platform currently boasts 2,500-plus users offering 1,800 skills from advanced email marketing to craft beer brewing.

Interested in the intersections of community, philosophy, and technology, John has been involved in projects like the Portland Made makers collective and the Chicago Free Skool. His passion for the startup community coupled with his own experience as a freelancer inspired him to create a space that would provide novices with access to clients and veterans with leads for advanced assignments.

Listen in as John shares his best tips for creating a killer profile, acquiring endorsements, and avoiding disputes on the platform. Learn how to use your aptitude in the creative and/or professional skills space to add an additional revenue stream to your repertoire – by way of HelpWith!

Key Takeaways

The HelpWith onboarding process

• Sign up with Facebook or LinkedIn
• Add a bio
• List your skills
• Name of skill
• What you can teach in an hour
• What qualifies you as an expert

The benefits of using the HelpWith platform

• Discoverability through SEO-optimization
• Opportunities for collaboration
• Simple payment process
• Reputation management via reviews, endorsements

John’s tips for making your HelpWith profile stand out

• Compose a descriptive, clear value proposition
• Include variations on a singular skill (i.e.: Photoshop, flyer design, web design mockups)

How to get hired for the first time on HelpWith

• Invite people you know to join the platform
• Ask them to vouge for you via an endorsement
• Endorsements translate directly into gigs

How HelpWith picks up where online courses leave off

• Many get stuck or lose motivation to finish online courses
• HelpWith provides one-on-one resource to get you ‘over the hump’
• Human interaction allows you to actualize new skills

How HelpWith helps entrepreneurs adapt to new technologies

• Freelancers who maintain their knowledge base as digital platforms change are rewarded for staying on the cutting edge
• Business owners can tap into the power of an expert for quick answers

John’s favorite simple trick to get inspired

• Choose three words you want to embody (i.e.: focused, present)
• Set a daily alarm on your phone as a reminder
• Realign yourself by asking, “Who do I want to be today?”

Resources

‘Getting Started’ Blog Post

Team Treehouse

OpenSesame

Udemy

Coursera

High-Performance Academy

Connect with John Connor

HelpWith.co

Many entrepreneurs – especially creatives – suffer from a bad case of Shiny Object Syndrome. We have so many ideas that it can be difficult to complete one project in its entirety before our mind has pulled focus to another.

Rita Morales helps business owners and entrepreneurs create and monetize a business they love through one-on-one coaching, custom web design, and mini-courses. Through her company, Rita Morales Brand + Business Design, she assists clients in gaining brand clarity and designing a robust marketing strategy. Rita’s interest in web design began when she was the office manager of a real estate firm, and she was tasked with maintaining the company website. Equipped with new skills like Adobe Illustrator and Photoshop, she got addicted to learning all things web creation and was soon designing her own. Rita moved to another corporate job but used her lunch hours to lay the foundation for her own venture – until the circumstances were right to escape corporate life and begin her own online business.

Today, Rita helps you combat Shiny Object Syndrome, define the branding for your business, and develop marketing strategies that generate results. Learn her techniques for short- and long-term planning, and discover how to harness consistency, accountability and focus on getting things done!

Key Takeaways

Rita’s recommendations re: the structure of a workday

• Consider using the first part of the day to grow your own business
• Then move on to client tasks in the second portion of your day

When to define the branding for your business

• Should be the first step
• May evolve over time as your mindset/desires change

How to establish your brand

• Identify your dream clients and their struggles
• Design your business to serve that specific audience

Rita’s best tips to curb Shiny Object Syndrome

• Finish one thing before you go on to the next
• Keep your eyes on your own paper
• Prioritize one or two areas
• Work with consistency, accountability, and focus
• Enjoy the results over time

Rita’s strategies for long-term planning

• Plan in three-month intervals
• Select one area of focus for each month
• Reverse engineer supports for that month’s focus area

How to stand out in a competitive market

• Create your user profiles and market yourself consistently
• Determine what you bring to the table that’s different
• Capitalize on your unique value proposition to connect with clients

Rita’s advice for using social platforms to expand your client base

• Bring value to your own Facebook group and contribute to others’
• Build and nurture your email marketing list

Connect with Rita Morales

Website

Instagram

Facebook

Facebook Group

So you’re tight on funds and can’t spend a ton of money to promote your business. What if I told you it's possible to generate a six-figure annual income with an advertising budget of under $100 per month?

LaShonda Brown is a CMO and Brand Strategist based in Virginia who launched About 90 Marketing to help small businesses accelerate sales and increase their digital footprint. She is adept at using social media tools to help stretch marketing dollars, and she shares that expertise via her new Periscope and YouTube channel ‘The Bootstrap Biz Advice Show’ to educate entrepreneurs. LaShonda’s experience in the world of promotion was born of necessity- her first venture was Transformation Theatre Company, an enterprise she began at the age of 18 with a $500 investment. In just a year and a half, TTC raised over $20k for charity. She is also the Co-Founder and Producer of Life Focus Pictures, a video production company she began with her husband in 2011 that provides engaging video content for clients including municipal communication departments and small businesses.

Listen and learn how to expand your client base by leveraging social media and teaching your current customers how to refer your business. No more excuses and no more waiting until you have enough money to start your business. LaShonda motivates you to get your show on the road – today!

Key Takeaways

LaShonda’s go-to strategies for generating business

• Utilize your personal Facebook page
• Celebrate wins for clients

How to kick off your business on limited funds

• Don’t wait until you have enough money
• Go for it NOW, while you are inspired
• Once you’ve generated some income, invest that money in your next venture
• Leverage sponsorships and donations to decrease expenses

How to establish credibility when you’re young

• People will be as confident in you as you are in yourself
• Present yourself with assurance and people are unlikely to ask your age
• Demonstrate value and clients will be even more impressed when they learn your age

LaShonda’s advice for juggling multiple responsibilities

• Start building the foundation of your business while you have the least to lose
• Gain experience and put resources in place while your business is still a side hustle

How to stay motivated

• Engage in passion projects (creative outlets you love, whether or not they generate profit)
• Invest in caring for your business’ greatest asset – YOU
• Don’t monetize every aspect of your life

LaShonda’s secrets to growing your client base

• Invest in relationships with clients (i.e.: go to lunch, happy hour, pedicures)
• Equip your current customers to refer you using a recommended landing page
• Establish your accessibility through visibility on social media

Why it’s important to find your lane and stay in it

• LaShonda underestimated how quickly About 90 would grow
• She was tempted to say ‘yes’ to every project and ended up overextended
• Creating a workflow to handle a new project costs more $ than it generates
• Repeat customers are more likely when you do what you’re best at
• Knowing your skill set helps you make the best use of your time

LaShonda’s top tips for entrepreneurs

• Customers justify decisions emotionally first, then logically
• If you let your work rob you of your joy, it will also rob you of sales
• If you are excited about what you do, clients will be too

Connect with LaShonda Brown

Website

YouTube Channel

Periscope TV