Alright – so today we’ve got the honor of introducing you to Lisa-Gaye Shakespeare. We think you’ll enjoy our conversation, we’ve shared it below.
Lisa-Gaye , thanks for joining us, excited to have you contributing your stories and insights. How did you scale up? What were the strategies, tactics, meaningful moments, twists/turns, obstacles, mistakes along the way? The world needs to hear more realistic, actionable stories about this critical part of the business building journey. Tell us your scaling up story – bring us along so we can understand what it was like making the decisions you had, implementing the strategies/tactics etc.
When I first started my business back in 2020, I’ll be very honest, I had no clue what I was doing. I just threw everything I loved all under one umbrella. It was a lot! I was teaching dance fitness classes several times a week, sometimes twice a day. I was managing social media accounts for small businesses (creating content, writing captions, posting and engaging) plus managing and doing the same for my own accounts. In addition to writing press releases and website copy for small businesses. I was doing this all by myself so needless to say, I experienced burn out real quick! I actually almost gave up on Shakespeare Agency because not only was I overwhelmed, the business wasn’t very successful. But having my hands in so many different pots allowed me to see where my true passion lied and that was with travel,
So in order to scale up, I had to scale down and pick a niche which is what I did in 2021. I decided to focus on travel, specifically to Africa and the Caribbean. The turning moment for me was realizing that people saw me as an inspiration in the field of travel because I was getting emails and DMs from my followers, as well as calls and texts from friends and family to help them travel the world. So, I redesigned my website, rebranded as a travel consultant, influencer and content creator and started offering travel services like custom vacation planning, curated travel itineraries, group trips and partnering with tourism boards, hotels and airlines to inspire my audience to travel.
By focusing on my niche and implementing marketing strategies to position myself as an authority in African and Caribbean travel, I’ve been able to slowly grow my business into what it is today. I’ve also scaled up by hiring a small team, where I have a virtual assistant, video editor and digital marketing manager to help take care of day to day tasks and logistics, so I can focus on delivering excellent service in order to meet my clients’ needs.

Lisa-Gaye , before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?
My name is Lisa-Gaye Shakespeare and I’m the passionate globetrotter and founder of Shakespeare Agency, a hub for all things travel, culture and adventure. I have a spirited heart and an insatiable curiosity to uncovering the beauty, history, and culture that our world has to offer. This has allowed me to venture through 59 countries and explored 25 U.S. states.
I have a B.A. and M.A. in broadcast journalism and marketing, so I channel my creativity and writing skills to produce captivating content that goes beyond the surface. My mission is simple yet profound: inspire others to travel, explore, and see the world through a lens of cultural richness and authenticity.
My company, Shakespeare Agency, provides services for two audiences: people who want to travel and see the world and brands within the travel and tourism industry who are looking for more exposure.
For those who want to travel and see the world, I offer the following services:
GROUP TRIPS
I curate custom group trips, specifically to Africa and the Caribbean, where I plan all logistics including itineraries filled with culture, adventure and soft life experiences, 4 and 5 star luxury accommodations, transportation, meals, local guides, excursions, professional photography and videography, welcome bags and more. Two of my upcoming trips for 2024 that have already launched are:
South Africa – October 12 to 23, 2024 (learn more at https://www.shakespeareagency.com/southafrica)
Sierra Leone – November 1 to 7, 2024 (learn more at https://www.shakespeareagency.com/thesankofaexperience)
VACATION PLANNING
I simplify your vacation planning process by handling all logistics from hotel suggestions to specially curated excursions and off-the-beaten-path adventures to authentic local experiences and transportation. This is ideal for solo travelers, couples, group trips, or family getaways, especially for those longing to explore the Caribbean or Africa, without the overwhelm of online research.
Schedule a quick 30-minute consultation call: https://app.acuityscheduling.com/schedule.php?owner=19705757&appointmentType=14974560
TRAVEL ITINERARIES
My specially curated and tailored travel itineraries are ideal for independent adventurers who enjoy arranging their own journeys but seek expert guidance. My travel itineraries are perfect because they include hotel recommendations, excursions, culinary hotspots, day-to-day itinerary breakdown, discounts and more!
Browse my Caribbean itineraries: https://www.shakespeareagency.com/category/all-products.
For those looking to break into the influencer industry or if you’re already in the field but want to learn how to monetize your platform, this service is for you:
TRAVEL INFLUENCER COACHING
I offer personalized consultations for aspiring or struggling travel influencers, where I address brand challenges and guide you step-by-step in my coaching program, empowering you to attract lucrative brand partnerships and achieve your goal of elevating your brand to getting paid for your travel expertise, paving the way for a successful journey in the world of travel influencing.
Schedule a call to jump-start your influencer journey: https://app.acuityscheduling.com/schedule.php?owner=19705757&appointmentType=25328692
For brands in the travel and tourism industry looking for exposure, I offer:
CONTENT CREATON
I specialize in tapping into the desires of travel audiences through compelling content and visuals that entertain, inform and convert. So I partner with brands including hotels, airlines, tourism boards, fashion and clothing brands etc. to provide more exposure to their destinations, products and services through sponsored social media content (reels, videos, carousel posts, stories and highlights), blog reviews, marketing assets, brand ambassadorship and more.
To work with me, email: [email protected]

We’d love to hear a story of resilience from your journey.
I quit my full time corporate job at the worst time possible! Right before we got hit with the pandemic. I decided to take a leap of faith and leave my cushy 9-5 with a guaranteed salary and amazing benefits to travel the world. I joined a company based out of London to manage and host group trips, worldwide. I thought it was my dream job at the time and was over the moon excited to start living out my dreams. But COVID stopped me dead in my tracks when the world shut down and I could no longer travel, which meant I lost my dream job in just a few months after starting it. I no longer had any income and I was also stuck in Miami, living on my friend’s couch because Jamaica had closed its borders and I could not return home. I went through a phase of depression where I completely shut down because I had basically lost everything and did not know what to do next.
After receiving several pep talks and constant motivation from a few of my close friends, I decided to try my hand at entrepreneurship and that’s how I launched Shakespeare Agency. I had no clue what I was doing, made several mistakes along the way, learned by trial and error and had to rebrand after a year.
Today, I’m proud of my growth and success of my business where I have partnered with over 50 brands in the travel and tourism industry, worked with over 30 clients on vacation planning and influencer coaching, hosted my first group trip to South Africa with 10 travelers and hosting 5 more group trips this year to Eswatini, South Africa, Sierra Leone, Ghana and Bali! There will always be obstacles and set backs, it’s just part of life but resilience keeps me going and I’m excited to keep elevating my company to the next level.

Any insights you can share with us about how you built up your social media presence?
I actually recently hit 50K followers on Instagram and now have a total of over 65K across all platforms. But honestly, growing your audience on social media isn’t an overnight success. It takes time, consistency, hard work, dedication and patience. I came across a screenshot in my phone of my Instagram page from 2018 and I had 3695 followers back then. This was when I had entered a competition to be the travel ambassador for Cancun and I had to get people to vote for me. So I was showing up on social media every single day, several times a day creating content to get my profile out there. While I didn’t win the grand prize, I made it to their top 50 (out of 3000 people) and that helped to put my page in the spotlight, where I gained new followers.
However, after the competition and the momentum fell off, my page wasn’t growing as much anymore because I wasn’t consistent with creating content as I was in the competition. So I had to get back to that, which is part of my growth strategy. Creating and posting content as much as possible and not just any content, but valuable and shareable content. You want your content to be “social currency” which means people feel compelled to send it to a friend because it’s educational, inspirational, entertaining, helpful or evoke emotions. Another great strategy to reach new people is to find your target audience and engage with them first. You can find your target audience through accounts that you love and are similar to yours, by interacting with the people who leave comments on those accounts. Genuinely engage with them and more than likely, they will do the same. I also suggest getting your content posted on feature accounts, which are pages with huge followings who repost creators’ content and tag them. That way you’re being exposed to their audience, increasing your likelihood of gaining new followers. Collaborating with other influencers in your niche is another way to build your audience, so sharing collab posts, going live with other creators, taking trips together, doing photoshoots etc will draw their audience to you and vice versa. My final tip for growing your audience is external traffic. Share your main page across all platforms (TikTok, YouTube, Facebook, Pinterest, LinkedIn etc) because if you have followers on those platforms, chances are they will follow you on your other social media pages.

Contact Info:
- Website: www.shakespeareagency.com
- Instagram: https://www.instagram.com/shakespeareagency/
- Facebook: https://www.facebook.com/shakespeareagency1/
- Linkedin: https://www.linkedin.com/in/lisagayeshakespeare/
- Youtube: https://www.youtube.com/channel/UC6X11B72CljbDuVzjesb1cQ
- Other: TikTok: https://www.tiktok.com/@shakespearetravels?lang=en Threads: https://www.threads.net/@shakespeareagency

