One might say that Lily was destined to be a venture capitalist. She started out angel investing when she was just 23 years old. Then, the role became a bit more formal when she joined the investment committee at Yard Ventures, Harvard’s alumni angel group.

As a Partner at Underscore, she is focused on making seed and Series A investments in Boston startups. The firm is focused on building a community driven model through its various initiatives like Underscore Core, a community of several hundred proven entrepreneurs, business builders, and domain experts that portfolio companies get to leverage to help drive their own success.

In this episode of our podcast, we cover:

* The current entrepreneurial vibe at Harvard and HBS.

* Lily’s experience after Harvard at Endeavor where she spent two years working with entrepreneurs in Chile.

* Her position at Facebook where she was part of a global growth & connectivity team that brought on 100M new users in 3 years.

* All of the details on Underscore including the firm's model and what makes the firm so unique.

* A discussion around why it might be a good idea for Boston companies to brag about success.

* And so much more.

If you like the show, please remember to subscribe and review us on iTunes, Soundcloud, Spotify, Stitcher, or Google Play.

It’s no secret that diversity is an issue in the tech industry, but it is an even bigger issue when you look at the venture capital industry. Rich has conducted a lot of research on this topic and based on his last report, only 2% of African Americans were represented as investors in the venture capital industry.

Rich is the type who takes action. By publishing his findings (which have been featured on TechCrunch, his personal blog, and in many other interviews), it helps to bring awareness to this key issue. In addition, Rich is also the founder of Stealth Mode, a community of more than 1,500 African American founders, operators, and investors.

After spending time in the venture capital industry at IVP and Venrock, Rich is now a Co-Founder & General Partner at a new firm called Equal Ventures, which recently announced a $56M first fund. The firm is focused on bridging the digital divide by investing in founders who are transforming legacy markets in industries like insurance, retail, supply chain and the care economy.

In this episode of our podcast, we cover:

* Rich’s early career in investment banking and how he landed in the venture capital industry, which involved a lot of cold emailing to partners at firms.

* All the details on Equal Ventures in terms of the firm’s thesis and the stage of investments they are focused on.

* What an investor is looking to get out of a first meeting.

And so much more.

If you like the show, please remember to subscribe and review us on iTunes, Soundcloud, Spotify, Stitcher, or Google Play.

At home, my family has a Cavapoo, who basically rules the roost. She has a big personality in a small frame and when she is sick, we definitely want to give her the best care possible.

In the world where personalized medicine is becoming very real for humans, why shouldn’t the same apply for pets? Enter Mixlab, the first-ever modern compounding pharmacy for animals. Mixlab customizes medication ingredients, strengths, forms, and flavors, specifically for your pet. The company announced $8.5M in funding last year and in addition to providing this very meaningful service, they also have a knack at wowing their customers, which we talk about in detail.

In this episode of our podcast, we cover:

* Stella’s background as a Designer and how that shaped her experience as an entrepreneur.

* What led her down the path of starting Mixlab and how she met her co-founders.

* The details on Mixlab and how their business model works.

* Advice for founders on hiring a designer.

* How a startup should think about branding and packaging.

* And so much more.

If you like the show, please remember to subscribe and review us on iTunes, Soundcloud, Spotify, Stitcher, or Google Play.

The fashion industry is constantly changing. It feels as though one week something can be in style, and the next it is already out of fashion. As a company, it’s nearly impossible to be able to keep up with trends and get them manufactured in a timely manner before the look goes out of style. Choosy is utilizing social media and algorithms to tackle this problem and this direct to consumer eCommerce company is on a path to revolutionize the fashion industry.

Jessie was born in China before moving to the United States while she was in elementary school. She originally envisioned a career in politics, but she ended up in finance which is where she met her co-founders for Choosy.

In this episode of our podcast, we cover:

* What it's like being selected and featured by Forbes as a 30 Under 30.

* Jessie’s early career and experience working in the finance industry and what that taught her.

* What led Jessie and her co-founders down the path of starting Choosy?

* All the details on Choosy and how their business model works.

* How Choosy is able to flourish in a highly competitive market.

* Advice on getting publicity for your startup.

* And so much more.

If you like the show, please remember to subscribe and review us on iTunes, Soundcloud, Spotify, Stitcher, or Google Play.

The insurance industry is extremely complex and can be very challenging to break into as an industry outsider. After being in a minor car accident, Snejina’s premium increased. Like any of us, she went online to find a better option only to realize that a marketplace for insurance didn’t exist. Existing sites were all lead gen. The complexity of the insurance industry probably kept other entrepreneurs from trying to build this type of marketplace, but it was the a-ha moment that led Snejina to take on this challenge, which has required a tremendous amount of grit and determination.

Insurify is reimagining the way you compare, buy, and manage your insurance online. Through artificial intelligence, they make insurance shopping simple, affordable, and hassle-free. The company recently announced $23M in Series A funding led by MTech Capital and Viola FinTech, with participation from Nationwide, Hearst Ventures, and MassMutual Ventures.

In this episode of our podcast, we cover:

* Snejina’s background growing up in Bulgaria and her professional career, including her move to the U.S.

* What led her down the path of starting Insurify and why she spoke with hundreds of people in the insurance industry before even starting to build out the core product.

* How she landed her first insurance carrier which created a snowball effect.

* The current state and scale of Insurify, plus its growth plans ahead.

* Advice on building a customer acquisition strategy.

* And so much more.

If you like the show, please remember to subscribe and review us on iTunes, Soundcloud, Spotify, Stitcher, or Google Play.

Lots and lots of startups and corporations have moved to an open office environment, which was supposed to foster collaboration amongst employees. As it turns out, according to research published by CNBC, “90% of employees working in offices with an open floor plan experience increased stress levels, conflict, blood pressure and turnover rates.”

Wow… shocking! So, how do you solve this issue without completely renovating your office, which would be very costly and disruptive? That’s where ROOM comes into play. They are rethinking the modern workplace with their innovative phone booth design. They are on to something, as the company has over 3,000 customers.

Growing up Brian always dreamed of being an entrepreneur and being a part of a startup. This is his second company, as he was previously a co-founder of a smart suitcase startup called Bluesmart, which was a Y Combinator company.

In this episode of our podcast, we cover:

* Brian's early experience teaching English in Ecuador and what that taught him about leadership.

* How he got into startups and his involvement with Bluesmart.

* The origin story of ROOM and how they discovered an underserved market that is helping to improve mental health and wellness in the workplace.

* The current stage of the company and growth plans ahead.

* Advice on setting up and finding the right manufacturer, plus why they choose to work with partners in Indiana and Portugal.

* And so much more.

If you like the show, please remember to subscribe and review us on iTunes, Soundcloud, Spotify, Stitcher, or Google Play.

It’s one thing to build a successful business, but it’s a whole different level if you can build a business out of doing good and creating better lives for others.

As you will hear in this podcast, Liz has a heart of gold and a do whatever it takes attitude to help others out in need. She has a history of volunteering and during her time at Harvard, Liz realized that there was an opportunity to help the less fortunate succeed through art.

This led Liz and her brother to pull together $4,000 from their personal savings to create ArtLifting. The company empowers artists living with homelessness or disabilities through the celebration and sale of their artwork. Its impact? Artists have earned over $1M from ArtLifting.

In this episode of our podcast, we cover:

* Liz’s experience and her background in volunteering for non-profits.

* The inspiration that ultimately led to the start of ArtLifting.

* All of the details on ArtLifting and the massive impact they are having on improving the lives of the homeless or disabled.

* How they raised capital from prominent investors, like the founder of TOMS Shoes, while building a social enterprise.

* The evolution of their business from a direct to consumer model to a more sustainable B2B focus.

* Advice for other founders around getting PR.

* And more!

If you like the show, please remember to subscribe and review us on iTunes, Soundcloud, Spotify, Stitcher, or Google Play.

It is a known fact that building a business is hard. It can be tricky because as an entrepreneur, you are filled with optimism. You are putting your blood, sweat, and tears into a business and it might feel like you are making progress and great traction. Yet, it could all just be a false positive. So, what happens if you come to this realization, then to put another layer of complexity to the scenario, the situation gets worse. An acquisition falls through and you are left with $1,000 in the company’s bank account?

Well, you could shut down the company, which would be a logical decision for most people. Or, you could pivot and bet your company on one piece of your platform.

This is exactly the scenario that happened to Ben. Pivots fail too, but in this example, it couldn’t have turned out better and it is a great story for all entrepreneurs to hear.

Privy is the leader in eCommerce marketing for small businesses and entrepreneurs. They are on a mission to be the front office operating system for eCommerce and its working. They have over 400,000 stores in 180 countries using their platform for marketing automation.

In this episode of our podcast, we cover:

* Ben’s early career and how he got into entrepreneurship.

* The first iteration of Privy and some of the lessons learned.

* Hitting rock bottom with the failed acquisition and the decision to pivot.

* All the details Privy’s incredible growth since and what’s in store for the future.

* Advice on communicating good & bad news with investors

* How to determine when to pivot your business.

* And more!

If you like the show, please remember to subscribe and review us on iTunes, Soundcloud, Spotify, Stitcher, or Google Play.

Kyle and I are from the same hometown, that being Manchester, NH. Growing up, I used to purchase my gear from his family’s sporting good store called Indian Head Athletics, so it is definitely a small world.

After graduating from Bentley, Kyle worked in the tech and went on to be part of the core leadership team that built Dyn, one of the most successful companies to come out of New Hampshire. Not only did they scale revenue to $100M in ARR, but Dyn also became one of the most important tech companies in the world as thousands of the top websites counted on the company for internet performance and security. Dyn was acquired by Oracle in 2016.

After investing in over 70 startups over the past decade and building companies as an operator, Kyle is leveraging this experience to help other entrepreneurs succeed through his firm called York IE (Investment Enterprise). This is a new value-add investment firm and operating company with a commitment to reshape the way startups are built, scaled, and monetized. In addition to York IE, Kyle is actively involved with several other companies as either an investor, operator, or board member.

In this episode of our podcast, we cover:

* Kyle’s background and some reminiscing about Manchester.

* All the details in terms of how he led corporate strategy, growth, and go-to-market at Dyn.

* How a massive DDoS attack at Dyn turned into a positive.

* Kyle’s experience as an angel investor.

* The details on York IE and how they differentiate from other investors.

* Advice for founders on building out an initial sales strategy.

* And more!

If you like the show, please remember to subscribe and review us on iTunes, Soundcloud, Spotify, Stitcher, or Google Play.

I once read a blog post that stated an interesting fact. The number of professional athletes in the U.S. is equal to the number of positions in venture capital. Needless to say, positions are scarce in the VC industry and they are highly sought after.

For Claire, she was determined to land a position in venture capital after getting her MBA at Wharton. She devoted months of her time sitting in coffee shops researching and learning the industry, while creating a recruiting plan, cold emailing VC firms, and offering her research to investors in hopes of landing an open position.

Well - Her determination paid off when she joined Corigin Ventures and she recently joined Highland to help the firm built out its New York office. Highland has a long history of success as a leading VC firm and their track record speaks for itself to the tune of 46 IPOs and 127 acquisitions.

In this episode of our podcast, we cover:

* How living in Kenya for six months influenced her career.

* Her experience working in investment banking during the economic crisis.

* How dedication and commitment through cold emailing landed Claire a position in the VC industry.

* All the details on Highland Capital Partners and what she is targeting for investments.

* How to get investors to respond to cold email pitches.

* What first-time founders can expect during the process of raising capital.

* And more!

If you like the show, please remember to subscribe and review us on iTunes, Soundcloud, Spotify, Stitcher, or Google Play.