
Jessica Billingsley
Founder | CEO | Public Speaker | Investor | Public and Private Board MemberSona Capital
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About
Jessica is a seasoned executive and innovator with decades of experience in frontier technology. She is named on multiple patents including advancements in supply chain technology and anti-counterfeit solutions using blockchain and NFTs. Her experience includes leading successful public and private companies as CEO and serving on multiple boards of directors. Jessica possesses in-depth expertise in private and public capital markets and has successfully navigated complex transactions to drive growth and business transformation. She is also FINRA securities licensed. Previously, as Founder, Chairman of the Board, and CEO of Akerna (Nasdaq: KERN), a Software as a Service ag-tech company, she successfully publicly listed, completed multiple accretive acquisitions, maintained market leadership for over a decade, and exited via strategic acquisition. Jessica currently serves on the boards of Gryphon Digital Mining (NASDAQ:GRYP), Nu Energy (NASDAQ:NXU), OARO, and the Young President’s Organization (YPO) Entrepreneurship Network Board. She has been recognized with numerous awards, including Inc. Top 100 Female Founder and Fortune’s Most Promising Woman Entrepreneur. Her insights and thought leadership have been featured in numerous prominent media outlets, in addition to her active contribution to Entrepreneur and Rolling Stone publications.

Jessica Billingsley
Published content

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Those companies unwilling to change may find it difficult to keep up with evolving customer needs. The only true constant in the culture space is change. With fast-moving trends, quickly shifting consumer behaviors and often unexpected global events, the culture space can be difficult to navigate if you’re not willing to roll with the punches. The ability to pivot, rethink their strategy and embrace change often separates thriving companies from those that fall behind. If businesses want to succeed in this industry, they’ll need to make adaptability an important part of their strategy and company culture. To help, 11 business leaders from Rolling Stone Culture Council describe the importance of adaptability in their own companies and offer up their best tips for successfully implementing it into your own organization.

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Many of today's most successful leaders got to where they are thanks to words of wisdom they received early in their career journeys. The lessons we carry from early in our careers often shape how we lead, create and collaborate in the present. Whether it was advice about trusting your instincts, staying true to your voice or learning from failure, the right words at the right time can echo for decades. Below, members of Rolling Stone Culture Council share the formative advice they received early on and how it continues to influence their work and perspectives today. Read on for their inspiring insights that you can take into your own professional journey.

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You don’t get to control what people remember. But you do get to decide how you show up in the aftermath.

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The decoupling of employment from economic growth is no longer a side effect of monetary policy.

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Vision matters. But execution is collective.

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Growing your business shouldn’t come at the expense of your current customers. In business, increasing sales — and, thereby, your customer base — is a natural goal for any entrepreneur. However, scaling too quickly or expanding into the wrong areas can risk alienating the niche market that helped establish your business in the first place. Losing these key customers could mean losing the stability, trust and feedback that acts as the backbone of your current success. For this reason, it's essential to find a balance between reaching new audiences and preserving the unique value proposition that attracted your target market to begin with. To help, experienced business leaders from Rolling Stone Culture Council share their insights on scaling the right way — a way that allows for healthy growth and expansion without losing sight of the niche market that made your business success possible.

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Mentorship can improve you as a leader as well — not just your mentee. Especially in creative-led industries such as music, art and even just general business, having a mentor can ensure someone starts on the path to success. A mentor can guide someone through the decision-making process, encourage a clever idea (or discourage a bad one) and help introduce them to other people and opportunities that could help define their career. However, mentorship is also leadership and, like any skill, can take time and intention to master. It may not come naturally to everyone, and those interested in taking on a mentorship role will need to first look at themselves if they want to later help others. Below, eight business leaders from Rolling Stone Culture Council share their insights on mentorship in the culture space and offer up their best advice for becoming a better mentor for any current or future mentees you may take on.

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Learn how to spot toxic patterns and find ways to approach work with a better mindset. The pursuit of success often comes with the pressure to constantly hustle. However, when you continuously push forward without balancing your own needs, ambition can lead to burnout. Striking the right equilibrium between drive and downtime is essential for maintaining long-term productivity and well-being. To help you do this, the members of Rolling Stone Culture Council share strategies for balancing motivation with rest to ensure you create a sustainable and healthy approach to work.

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Take your team to the next level with these expert-approved motivation strategies. Great managers know that bringing out the best in their teams requires more than just setting expectations. Your employees have to feel motivated, supported and empowered to excel — and that all starts with the work environment. Whether through fostering open communication or aligning employee strengths with responsibilities, the right strategies can unlock your team’s full potential. Read on for advice from Rolling Stone Culture Council business leaders about effective management approaches that drive performance and boost morale.

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The future doesn’t wait—and neither do the innovators reshaping our world faster than ever before.

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Watch out for these telltale signs that your brand may need some fine-tuning. Brand alignment is crucial to any business's success, both on an initial and ongoing basis. If your brand doesn't deliver on its mission and value proposition — or communicate this information in a way that resonates with your target audience — you might find yourself with decreased engagement, fewer sales and a lack of clarity on how to move forward. But how do you know if your brand is misaligned, and what can you do to fix the problem? Here, the members of Rolling Stone Culture Council share some red flags that your brand needs realignment, along with actionable steps to get things back on track.

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Leadership skills can never truly be mastered, as they are something that should evolve over time. Professional development is often focused on improving yourself and your skills to help you move up in your career. The better you are at something, and the more skills you have, the higher on the ladder you can climb. But no one ever truly reaches perfection — not even leaders. Learning doesn’t stop once you become the boss. In fact, it’s even more important that you continue to learn as a leader if you want to grow, innovate and succeed as a business. So what are some of the things you can learn? Here, 12 business leaders from Rolling Stone Culture Council discuss the things about themselves they have had to work on improving over the years and why it’s so important other leaders do the same.

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If you want to convince someone to buy from you, first you have to understand the value you’re offering. When you run a business in a creative industry, it might not always be clear how to monetize your work. Whether you’re an independent artist, a freelance creator or any other form of solopreneur, one of the first steps on your road to success is managing to land your first sale — and that can be a tricky endeavor on your own. Having each worked in the culture space for some time, the members of Rolling Stone Culture Council know what it takes to run successful businesses in creative industries. Here, they weigh in with words of wisdom for aspiring or current entrepreneurs on how to land that elusive first sale, and what it takes to keep your business going even after you’ve earned your first customer.

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Don’t let a few roadblocks keep you from trying your hand at business ownership. No business is without its challenges. Even the most successful of companies today started out as simple ideas that had to be worked on and evolved over time. And with about 20 percent of businesses failing to make it past their first year, it’s not uncommon for the obstacles in the way of entrepreneurial success to become too difficult for aspiring business owners to overcome. In the culture space, where so much of a company’s success depends upon the trends and desires of the day, carving out a secure space in the market can be an even greater challenge. For those entrepreneurs willing to take the leap, the business leaders of Rolling Stone Culture Council discuss 10 key hurdles aspiring business owners will need to overcome if they want to succeed in the culture space today — and why doing so will make them stronger over time.

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Learn what it takes to turn your workplace into an environment where employees want to grow their careers. As new generations enter the workforce, a shift in employee expectations has challenged traditional approaches to retention. Offering competitive salaries is no longer enough — today’s employees want more from their workplace experience. This changing environment has made long-term employee retention feel increasingly difficult for many businesses. To help, Rolling Stone Culture Council members share what it takes to build a workplace where people want to stay and grow. Follow their recommendations to make your workplace a destination employees won’t want to leave.

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AI isn’t just about cutting-edge innovation or tech buzzwords. It’s about solving real business problems and creating tangible, measurable value.

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Proper training can ensure reps are prepared to handle any problem that comes their way. Because they have direct interactions with customers on a daily basis, a company’s customer service team plays a large role in that organization’s success. Quality customer service will not only impress new customers but will also be a key motivator in their decision to stick around for the long term. This means that training customer service reps on how to do their job efficiently and with quality and positivity in mind is an important task that leaders shouldn’t take lightly. As business leaders themselves, the members of Rolling Stone Culture Council know what it takes to provide great customer service. Below, they each detail one area they believe more customer service teams should be trained on in order to be successful and the impact that has on a company’s bottom line.

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To persuade a brand to work with you, first think about how you can help them. In a saturated market, it can be difficult to stand out — especially on your own. A great way to reach new audiences and leverage resources that may not normally be available to you, however, is to collaborate with another business in, or even outside of, your industry. A product or campaign that takes advantage of both teams’ strengths may be just what you need to get you both noticed by potential customers. However, approaching another company can feel intimidating, especially if you’re a small business and unsure of what you might bring to the table. According to the business leaders of Rolling Stone Culture Council, taking the following eight steps can help boost your confidence. Here, they offer up their best tips for approaching another brand or business about a collaborative partnership and what you can do to guarantee their interest.

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When it comes to human-to-human connection, AI can be a valuable tool. As AI becomes more and more commonplace in business, there are some leaders who worry about it replacing the human element of customer service and engagement. Will customers really be happy talking to AI over another human being? Will business lose its personal touch? While AI is certainly poised to change the way business is currently conducted, many leaders believe that technology can be used as a key tool for bettering relationships between customers and companies — not replacing them. Below, 10 business leaders from Rolling Stone Culture Council weigh in with their thoughts on technology in business, each discussing one way a business can leverage technology to build better relationships with its customers and what's worked well for them.

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The support and experience of others may just be the solution you need. Success is often not a straight line; it’s full of ups, downs and plenty of surprises. In entrepreneurship, the path to success comes with obstacles you’ll need to overcome if you want to continue on. Many entrepreneurs share similar obstacles, and some may be more unique to specific situations or people. However, when all is said and done, it’s the way an entrepreneur solves each problem that can serve as a guide for others to solve their own. Below, 11 members of Rolling Stone Culture Council each share one major struggle they've faced as an entrepreneur, the steps they took to overcome it and how other entrepreneurs might learn from their journey.

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Remember, success is not just about the big wins but also about the consistent, small actions and choices you make along the way.

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Yes, the demand for computing power is skyrocketing. But so too are our solutions for meeting this demand sustainably.

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Rather than complicating the leadership dialogue with excessive details and metrics, this approach can help streamline the conversation.

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Your willingness to learn and grow has a major impact on your ability to win in business. The business world is full of ups and downs. One day you’re succeeding, and the next day you’re not. This can be especially true of the culture space, where trends can change daily and consumers’ opinions evolve equally as fast. Entrepreneurs who develop a growth mindset — or the belief that persistence and effort lead to success — are more likely to thrive in this type of environment, making it an essential trait to cultivate for culture space leaders. As leaders in the culture space themselves, the members of Rolling Stone Culture Council know what it takes to succeed in today’s marketplace. Here, they discuss the top reasons why business leaders need a growth mindset and the impact that mindset has on their ability to lead well.

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Building the brand image you want starts with smart PR moves. In business — and especially the culture space — what the public thinks of your brand is everything. Do they find you trustworthy and reliable? Do they think of you as innovative, cool or luxurious? Controlling the narrative around your brand is key to ensuring you create the image you’re after — and to ensuring you’re reaching your desired target audience. However, public relations is an art as much as it is a science, and many businesses that don’t have experience in this particular area can end up making mistakes that could damage their reputation in the short and long term. To avoid these same blunders, consider this list of common mistakes as outlined by the business leaders of Rolling Stone Culture Council. Below, they detail why these mistakes can be detrimental to your brand goals and advise what actions you should take instead.

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You may have to adapt your current business plan. Much like technology, culture can change at the drop of a hat. People’s tastes, what’s “in” and “the next big thing” are constantly evolving, whether in reaction to current events or the latest innovation in a particular industry. Those entrepreneurs hoping to make it in this space must be able to thrive in a changing environment, adapting their business when it’s needed and sticking to the plan when it’s not. But this isn’t the only way to get ahead in the culture space. According to the business leaders of Rolling Stone Culture Council, embracing the following habits can give hopeful entrepreneurs a leg up on the competition and ensure they find true success in the culture space and their overall careers.

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Much like the traditional love languages developed by Gary Chapman, financial love languages describe how we derive value and satisfaction from money.

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We're entering an era where agility and foresight aren't just advantageous — they're essential.

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If you’re feeling nervous about a media appearance, consider these tips to help you prepare. Not all business leaders are natural speakers, but they often need to promote their businesses on TV, the radio, podcasts or other media channels. For the inexperienced speaker, this can be a terrifying prospect. After all, the impression you make as a leader will be the first impression many viewers or listeners have of your business. As experienced business leaders themselves, the members of Rolling Stone Culture Council have a few tips to share that can help you prepare for your first media appearance. Follow one or more of their suggestions to not only nail your interview but impress potential customers as well.

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If you want your business to go viral, then apply these tips to go the extra mile. Whether it’s “going viral” or becoming “the talk of the town,” generating buzz around your business is essential if you want to grow your audience and, consequently, your bottom line. General marketing efforts are a good start; however, you'll need to do more to make a big name for your business. According to the business leaders of Rolling Stone Culture Council, the following 10 strategies can give your brand the boost it needs to really take off. Consider adopting one or more of these tactics to build buzz around your business, get your product in front of more consumers and increase your sales as well as your odds of success.

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Broadening the pool of AI development contributors beyond corporate labs is not just ideal — it's essential.

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Consider these pivotal factors when partnering up for a campaign. Partnering with the right creative agency can be the difference between a lackluster campaign and a resounding success. As businesses seek to captivate audiences in more innovative ways, the selection of a suitable agency becomes a critical decision. But how does one discern the ideal match amid a sea of options? Here, Rolling Stone Culture Council members explain the crucial factors that demand your attention when evaluating potential creative agency partners. From a track record of creativity and adaptability to a shared understanding of the brand's vision, navigating these considerations can pave the way for fruitful and inspiring collaborations.

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AI in the workplace could have some definite benefits — as well as some downfalls. In an era marked by the rapid evolution of artificial intelligence (AI), businesses are increasingly presented with both unprecedented opportunities and ethical dilemmas. As organizations consider integrating AI technologies into their operations, the intricate web of challenges surrounding their creation and implementation continues to spark controversy. Before taking the plunge into the realm of AI, prudent business leaders find themselves standing at a crossroads, grappling not only with the promise of innovation but also with the potential pitfalls that lie ahead. To offer their insights, Rolling Stone Culture Council members share the critical questions business leaders should ask before making AI a part of their business in any meaningful way.

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From prioritizing necessary but high-cost items to leveraging technology, learn more about how to manage costs wisely while scaling your business. When it comes to scaling a business, managing finances effectively is crucial for success. As a business grows, so do its expenses, and without careful management, costs can quickly spiral out of control. But how can you keep costs under control while expanding your business? Below, Rolling Stone Culture Council members share expert tips and insights for managing costs wisely when scaling your business. From tracking expenses to optimizing processes and negotiating with suppliers, these strategies can help you build a sustainable business while keeping your finances in check.

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May 1, 2023
The arrival of Web 1.0 and Web 2.0 transformed how we consumed content, and now we're witnessing another groundbreaking shift with the rise of Web3.

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Jun 9, 2022
It was a broad perception that these southern states would never legalize cannabis use — but things seem to be changing.

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Tech may be the right tool you need to get ahead. When used correctly, technology has the power to help make people better versions of themselves — whether that’s someone who never misses an event or someone who can be reached at a moment’s notice. This applies to the workplace as well, with an ever-increasing number of software, apps and tools designed to help busy professionals get more done in their day. For many business leaders, properly leveraged technology is the secret to their productivity success. Below, a panel of Rolling Stone Culture Council leaders discuss the ways they use technology to help improve their productivity or work motivation throughout the day and why these strategies work so well.

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Preparing for success tomorrow means taking thoughtful steps today. In business, often the only thing that is certain is uncertainty. You never know if your product will sell or if you’ll make enough money to last another year or if being an entrepreneur is really your true calling. While no one can predict what tomorrow will bring, there are ways you can help to guarantee your business will remain successful no matter what the next day may bring. Below, a panel of Rolling Stone Culture Council members offer their best tips for “future-proofing” your business and explain how these tips will help ensure your business is secure.

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Mar 23, 2022
The southern region of the U.S. possesses the immense potential to be a cannabis economic powerhouse.

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When you feel like your creativity has dried up, these resources may get your thoughts flowing again. As many creative minds will tell you, creativity isn’t something that is just “always on.” Rather, creativity comes in waves, ebbing and flowing each day in what can often seem like random intervals. When you run a business that relies on innovation, however, it can be difficult to wait for inspiration to strike. To get your creativity flowing, you’ll need to seek out your own sources of inspiration. Below, a panel of Rolling Stone Culture Council experts share their own go-to sources of inspiration and how you can regain your own creativity by leveraging them yourself.

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Jan 13, 2022
What inspires entrepreneurs each day doesn't have to come from the business sector. As any entrepreneur will tell you, running a business is a tough job. Finding the motivation to bring your all every day is a task in and of itself as you can easily become overwhelmed by the responsibility of constant planning, innovating and ensuring your team is well taken care of. Having something or someone to draw from for inspiration, then, can have a major impact on an entrepreneur’s outlook. But you don’t have to look to the business realm to be inspired. To share what has served as their biggest source of non-business inspiration, a panel of Rolling Stone Culture Council members each discuss what (or who) inspires them as they lead their companies now and into the future.

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B2C companies should prioritize increased transparency in their processes.

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Sometimes scaling quickly isn't the best path forward. While it's every company's hope to grow, what many companies may not realize is that quick, explosive growth might not actually be the best way to scale. Though some companies may not have a choice if they experience sudden “overnight” success, those actively looking to skyrocket in popularity and sales need to consider a few important points first. Below, 11 business leaders from Rolling Stone Culture Council list some of the points an entrepreneur should be concerned about if they’re looking to grow their company quickly, and offer their best tips for scaling successfully in the long term.

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You can’t grow your business without facing a few obstacles along the way. Leading a business often comes with its own unique challenges, some more difficult to navigate than others. What separates great leaders from good ones is the ability to face those challenges, overcome them and come out stronger and wiser on the other side. No matter the challenge, there’s always a lesson to be learned that can either overwhelm you or help your business grow. But learning those lessons can often be a challenge in itself. Below, a panel of Rolling Stone Culture Council leaders detail the lessons they’ve learned from some of the most difficult business situations they’ve faced and how they became all the wiser for it.

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Cannabis technology businesses are like distinctive creatures in a unique lagoon.

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Encouraging growth and development sets up the employee and the company for future success. In business, creativity sparks creativity, and the more employees are allowed to learn and grow in their positions, the more ideas and innovation they are able to bring to their company as a result. Continued learning, therefore, can be a powerful benefit to the company and employees within it, offering them new and exciting challenges and opportunities for promotion and leadership. To encourage this growth and development, employers can opt for a multitude of strategies. Business leaders themselves, the members of Rolling Stone Culture Council each shared the way in which they and their department managers inspire their employees to pursue continued growth and learning throughout their careers.

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For these business leaders, hindsight is 20/20. Starting a business can be an intimidating undertaking, especially when it’s your first one. You’re often feeling imposter syndrome in full force, and no matter how much planning and research you do ahead of time, rarely does any aspect of business go how you’d expect. Because of this fact, for many entrepreneurs, hindsight is 20/20. Now with established careers and businesses, they can better reflect on what may have gone wrong or what they could have done better when they first started out. Below, a panel of 14 Rolling Stone Culture Council members share the lessons they wish they had known when starting their businesses and how that knowledge may have helped them grow along the way.

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The most valuable information at your disposal is what your customers think of you. No matter what type of business you run, your customers always have an opinion. From being completely happy with your service to thinking your product needs a total overhaul (and every opinion in between), your customers’ opinions can be as diverse as they are. It’s the companies that know how to harness this feedback to inform their decisions that are able to please their customers the most. The first step, however, is to collect that customer feedback. Below, 11 members of Rolling Stone Culture Council suggest a few ways of doing that and what you should be doing with the feedback once you have it.

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Offering a top-notch customer experience is more important than ever, but you need the right strategies first. When designing a better customer experience, many organizations today are focusing on convenience. Whether it’s companies finding inventive ways to deliver their products or working to make their customers’ lives easier, convenience has a positive effect on customer satisfaction. But to make sure you’re delivering the best overall experience, you’ll need to start with a few simple steps. Below, 10 Rolling Stone Culture Council members each shared one thing leaders can do to maximize convenience and create more happy customers.

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Jul 29, 2021
How will you help your business tap into this unprecedented access to innovation and harness it for benefit?

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Creating a mutually beneficial partnership means laying the groundwork for success upfront. When businesses partner together — whether for an ad campaign, product launch, promotion or any other reason — both should reap the rewards. But to ensure it’s a successful endeavor for all parties involved, there may be some necessary planning to do. While the process doesn’t need to be complicated, there are some important steps to be taken and considerations to be made before either business will feel satisfied. To shine some light on those steps, 13 members from Rolling Stone Culture Council list some of the key actions to take to make sure your next partnership is a successful one.

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Innovation across industries often signals big changes for our everyday culture. Continuous innovation is a hallmark of the modern business world. It can happen anywhere and in any industry, and it often results in a positive transformation of business processes and workflows. The culture space specifically has experienced a lot of transformation in recent years. As leaders in their respective fields, the members of Rolling Stone Culture Council are constantly looking for ways to leverage new innovations to improve their companies and bring value to their customers. Below, 11 of them share which upcoming industry innovations and subsequent changes they're most excited about and why.

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How can cannabis operators in legal markets leverage data to optimize and grow their businesses?

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May 10, 2021
Blockchain and cryptocurrency continue to be buzzwords across a variety of industries.

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When your usual outlets aren't available to you, it's important to find alternate coping mechanisms. It’s no question that the last year has been challenging for everyone. Even with the hope of "normalcy" on the horizon, people are finding it difficult to cope with the ongoing pandemic on top of the challenging social and political climate. With many outlets and resources inaccessible at this time, it’s even harder to find ways to de-stress. To help, a panel of Rolling Stone Culture Council members shared activities and methods that can aid in coping with burnout during multiple crises. Follow their advice to find healthy ways to deal with the stress of the modern world.