Nov 15, 2022

Female Investors: Protips and Insights for The Next Generation

Yasmine Morrison talks about Web3 investing at the 2022 Glaring Gap Summit in Tampa

PS27 Ventures’ Top Five Highlights and Photo Gallery from the 2022 Glaring Gap Summit

It was a windy morning in Tampa as dozens of female investors gathered at Embarc Collective for the Glaring Gap Summit. The annual summit is Florida’s premier women investor event made up of just 50 Florida-based women who will positively impact the future of Florida’s investment landscape. Christine Caven, PS27 Ventures’ Director of Communications, was selected to attend the gathering designed to maximize learning and connections and learn from women investors. Below are our top five highlights and photo gallery from the event.

Keynote Regina Marrow, CIO for ReliaQuest

1. Scaling Your Career 

The Glaring Gap Summit kickoff was filled with handshakes, conversation over coffee, and a delicious breakfast spread. Regina Marrow, the CIO of ReliaQuest, took the stage as the opening keynote and shared her lessons learned in her non-linear path to the executive leadership team of a unicorn company

What is a Unicorn Company? The term unicorn refers to a privately held startup company with a value of over $1 billion. It is commonly used in the venture capital industry.

Regina Marrow is responsible for Reliaquest’s global internal systems, infrastructure, and technology initiatives for scaling internal platforms and deriving data-driven insights to keep pace with the company’s growth and geographic expansion. 

On stage, Regina related her perspective on productivity to the audience through a Mark Twain quote. 

Mark Twain once said, “Eat a live frog first thing in the morning, and nothing worse will happen to you the rest of the day.” 

“What is your frog? The first thing you need to accomplish in the day is important.You should ask yourself, what is the one thing that I’m excited about today? What is something that can trip me up today? What is something you need to get done, but today is not the day?” 

Regina Marrow

Regina shared her experience working for more than 20 years in IT, having previously served as the CIO at ConnectWise and as the Executive director over IT for the North American operating unit for Gerdau. 

What practices do you take in investing?

“I handled the investments for our family. B-class stock from Brookshire Hathaway. Over 20 years ago, there was not the opportunity for individuals to invest in startups. Not at the scale that is available today.”

Regina Marrow

There are great companies solving big problems and having meaningful growth. Tom Wallace and Florida Funders piqued her interest in investing. What they were looking for resonated. The focus was on the founder, the problem they were solving, and their leadership team. How were they (the founders)  thinking about customers and growth?

Regina closed her talk by reminding the audience of the importance of connecting and networking in the tech community. Her first investment in startups came after a friend invited her to learn more about Angel Investing and Venture Capital. 

Deborah Ellinger and Artemis Emslie discuss leadership at Glaring Gap Summit

2. Ask, Brand, Connect 

Seasoned board leaders Deborah Ellinger and Artemis Emsile shared tactical examples on how to level up your leadership – all the way to the board room. 

Deborah Ellinger is a former CEO with extensive global board experience who is focused on the intersection of consumer products and services, technology, and digitization. Deborah currently serves as the Board Director of iRobot and Covetrus. 

Artemis Emslie is the CEO of Cadence Rx, a patient-first technology designed to provide a better patient experience and improve medication management. Artemis leads the company’s strategic growth and successful scale. Currently, she serves on the advisory boards of AffordIt and the American Heart Association Metro. 

To kick off this session, Deborah asked the room for a raise of hands, “How many women in the room asked for more money when they were offered their first job after college?” 

Just a few hands in the room were raised. A glaring statistic shares that when graduating college and having their first job offer, 65% of men ask for more money, and only 8% of women ask for more money. Later, this statistic translates to male vs female investors, an industry dominated by men.

“One of the things I see with women is that they do not ask for enough capital.”

Deborah Ellinger

When building a company, Deborah and Artemis talked about what to focus on when capital is limited. 

“Brand is important – but you don’t have to spend a lot of money to get to brand. Understand where you need to invest: people, culture, and networking. Understand the game plan and the risk in the business. By the time it’s in the newspaper – it’s too late. I invest in women that do products for women. I love investing in women.”

Deborah Ellinger

When it comes to calculating value, Artemis Emsile shared the logic behind her typical investment. One must take a look at the total addressable market, top level, and bottom up. What will it cost to access the market? What is the price point of the thing you’re selling, and how many people will buy it? 

Deborah and Artemis closed the fireside chat with an inspirational message:

“Have courage, conviction, and ask for more.” 

Deborah Ellinger
Kristina Barrett explains Venture Capital and how to participate as an investor

3. Capital Deep Dives: Equity Crowdfunding, Web3, and Venture Capital 

Equity Crowdfunding 

Caitlin Szikszai, the Senior Investment Team Associate at Republic, shared how she helps early-stage founders raise capital through equity crowdfunding. 

What is Equity Crowdfunding? Equity crowdfunding allows startups and early-stage companies to issue ownership stakes to many investors in exchange for capital. Shareholders stand to profit if the company does well but can lose all of their money if the company fails.

Through the Republic platform, people can invest as little as $50 to diversify their portfolio. Companies can raise up to $5M yearly from accredited and non-accredited investors.  

Embarc Collective host Allie Felix shared that she has personally invested through Republic. 


Yasmine Morrison, Director of Venture Capital at Florida Funders, shared the latest trends in Web3 investing and how startups can prepare for the newest version of the internet. Yasmine has a diverse background, having spent 7 years working across the globe, from co-founding startups to working in consulting with global companies, including Toyota and Amazon. 

What is Web3? Web3 is an extension of cryptocurrency, using blockchain. Web3 is the third version of the internet. Web1 was simply reading through plain text websites. In 2005, web giants like Facebook and YouTube came into the scene where users could read and write. Users could contribute to the web, but the giants would own your work. Web3 is read, write, and users can have ownership through blockchain.

Yasmine shared the three things to consider when raising venture capital for your Web3 startup:  

1. Prepare – From a web 3 perspective, get your token mix; investor-customer relationship management is important. Find investors in Web3 that make sense for you: Tier 1, Angel Investors, and Strategic Partners.

2. Start with Angels – Get that early capital committed before going to venture capital. 

3. Closing – Remember that this is a partnership between you and the investor. It should be good for both of you and fair on both sides.

From a web3 perspective – are you giving away tokens? What differentiates Web3 fundraising from other capital is using tokens.

What are Web3 tokens? Web3 tokens are digital assets that are associated with the vision of creating a decentralized Internet. Startups can offer investors tokens on a side letter in exchange for capital. 

“What I love about Web3 is that it’s giving ownership to everyone.”

Yasmine Morrison

Venture Capital 

Kristina Barrett,  Principal at Cultivation Capital, took the stage to share her best practices for raising venture capital. Kristina is an alumnus of the Venture for America Fellowship and graduated from Harvard University. Before joining Cultivation Capital, Kristina worked in a leadership role in an early-stage health tech startup. 

What is Venture Capital? Venture Capital (VC) typically refers to the funding provided by investors to small or start-up businesses with strong potential for growth. A venture capital fund is a form of private equity raised from private and institutional investors, such as investment banks, insurance companies, or pension funds.

“A lot of early-stage money comes from the region that you are in – know your local VC providers.” 

Kristina Barrett
PS27 Ventures participates in the Glaring Gap Summit

This can help get warm intros into venture capital companies when you are raising. If you’re a founder, a limited partner can connect you to venture capital. If an LP recommends a company, the VC will take a hard look at those companies.

One pro tip from Kristina was to be prepared for questions, “A pitfall is that the founders do not have the numbers at their fingertips; margins, revenue, traction, and a data room are essential to early stage.” 

At PS27 Ventures, we ask founders a lot of questions before investing. After a company has submitted their pitch deck for review, we set up an introductory meeting, a financial review takes place, and if all goes well, we conduct a 4-hour deep dive called a “workout” where we ask questions and find out how the founders respond to feedback and if the investment is a good fit for both parties. Our typical investment ranges from $250K up to $1M. If you are a founder raising venture capital, you can submit your pitch deck here.

Angela Lee, Professor of Venture Capital Practice at Columbia Business School on Zoom at Glaring Gap Summit

4. Investor Education Training 

Following a short break for lunch and networking, Angela Lee Zoomed into the event for her session on investor education training. 

Angela Lee is a Professor of Venture Capital Practice at Columbia Business School, bringing 20 years of innovation, strategy, and entrepreneurship experience to the classroom. She is a startup investor and founder of 37 Angels, where her curriculum has been used to train the next generation of female investors and students on the practice of startup investing. 

Angela shared Angel Investment advice for newbies. 

“Get out there and listen to pitches as much as you can. Develop your gut.” 

Angela Lee

From deal flow process and metrics that matter to term sheet templates and ownership calculations, Angela walked the budding investors through all of the basics. Angela recommended resources like CrunchBase, PitchBook, TechCrunch, and Halo Report for keeping up with early-stage investment news and data.

For the final assignment, diligence groups were created and assigned to the investors in the room. The women investors observed pitches from female founders building early-stage startups at Embac Collective and were assigned homework to evaluate an assigned startup using a due diligence template.

“If you’re a good founder, you should have 5 VCs who want to give you money.”

Angela Lee
Investors and Female Founders network Embarc Collective

5. Glaring Gap Summit 2022 Reception 

As the event came to a close, the “investors in training” and women startup founders had the opportunity to network and enjoy light refreshments in the Embarc Collective kitchen. 

Overall, we highly recommend the Glaring Gap Summit. From VC basics to deep dives into investment strategy, this crash course gives women the opportunity to explore building wealth and investing in the Florida Innovation Ecosystem. Want more from Glaring Gap? Follow PS27 Ventures on TikTok for our highlight video.

About Embarc Collective 

Embarc Collective is a startup hub helping founders in the Tampa Bay region build bold, scalable, thriving companies. 

Embarc Collective offers hands-on support driven by the unique goals and needs of each member startup at its headquarters in downtown Tampa. Embarc works with over 125 early-stage startups and is the fastest-growing startup hub in Florida.

Keep up to date with PS27: