Investing in the Retail of the Future

Hear directly from an investor about fundraising tips, learning from startup failures, and how to spot trends in the startup eco-system.

March 25th, 2017   |    By: Donna Griffit    |    Tags: Culture, Idea Validation




“Many people in the startup ecosystem tell you that it’s true that you learn more from failure than from success, and I agree. I learned so much from the failure of my startup, most particularly and importantly, that it’s okay to fail. Our culture rewards success above all, so it can be hard to tell your family, your friends and your colleagues that you’ve had to shut down your business because it just wasn’t successful. It was personally wrenching. I hated those conversations and tried to avoid having them in the early days after we shut down the business. But as I started to talking to other entrepreneurs, friends and former colleagues, many had a failure story of their own, and had used that experience to be more successful in the future. And that was reassuring to me, and helped me come to terms with it.”

Sapna Shah, Angel Investor with Red Giraffe Advisors, bravely states what many people are thinking but don’t have the courage to admit. And Sapna learned this through her own entrepreneurial experience. Since becoming an investor 3 years ago, she’s invested in 12 companies and done two follow on investments, almost all in the retail tech, fashion tech, and e-commerce segments.

The Sausage King of Baltimore

Born in Pennsylvania, she grew up in the suburbs of Baltimore and was steeped in entrepreneurial spirit from the time she was born. Her mother ran a daycare center out of the family’s home and her father worked at Parks Sausage Co, a local company famed for being the first African-American-owned firm listed on the New York Stock Exchange. He eventually became the Executive VP of the company and he and other management members bought the company back from a conglomerate. After leaving Parks, he launched a small business in the home audio/video/automation space. Sapna was fascinated by business and the stories her father told over the dinner table and also by technology and computing in its very early days in the 80’s.

“In high school, I always used to say that I was going to grow up to be the CEO of IBM. Obviously that didn’t happen!”

The Paper-Resume Trail

Sapna graduated with a BS in Economics from the Wharton School, a BA in East Asian Studies from the College of Arts and Sciences at UPenn and an MBA from the Columbia Business School. Upon graduation Sapna set off on a typical route, working first as a Credit Analyst at Morgan Stanley and then as an Investment Banker at Punk, Ziegel & Knoell. But then life took a twist which set her career in an entirely different direction.

While applying for summer internships at Columbia in 1997, prior to the days of online recruiting, she accidentally dropped her (paper) resume into the wrong on-campus recruiting slot. Unbeknownst to her, the resume went into a slot of a job at Gap, Inc. in San Francisco. She got the job and spent the summer in an internal consulting role.

“It was a fantastic time to work at Gap — Mickey Drexler was CEO, the “Khakis Swing” ad campaign made Gap cool, the company had just launched e-commerce — I fell in love with retail and never looked back! I’ve worked in and around retail ever since.”

From E-commerce Exec to Entrepreneur

Sapna’s first taste of the entrepreneurial life was during the first dot com boom in 2000. At the time she was temporarily living in Denver and she worked with a co-founder on an ill-fated startup in the career management space which really never got off the ground. She went back to retail where she worked as an Executive Director at Linens ‘n Things. This would again be a pivotal position, because it was there that she met her colleague, Lisa Walters, who would become her two-time co-founder.


In 2006, Lisa and Sapna launched an independent equity research company, Retail Eye Partners, a successful services business to Wall Street. Later, in 2011, Lisa and Sapna launched a menswear ecommerce startup called “Mind the Chap.” Though there were successes with it, they ultimately felt it wasn’t scalable and shut it down in. Sapna also exited Retail Eye, selling her shares to Lisa in 2013.

“Running both businesses at once was insane now that I look back on it…I learned a lot about the hard things in ecommerce startups, from difficulties in logistics, customer acquisition and even how to handle credit card and returns fraud. All of those learnings have been incredibly helpful as I advise startups in the ecommerce space. Frankly, without having seen some of the ways ecommerce can fail, I’m not sure my advice to my portfolio companies would be nearly as valuable today.”

Investing in the Future of Shopping and Retail

In late 2013, while shutting down Mind the Chap and selling Retail Eye, Sapna was looking for a way to stay involved in the startup community, though she didn’t want to be an entrepreneur again right away.

“A friend of mine was looking to raise money for his new retail-related startup, Iterate Studio, a platform that helps traditional enterprises connect with and pilot new technologies from startups. I thought, ‘this could be an interesting path for me.’ I started getting involved in the angel community in NYC and here we are 3+ years later. I learned so much from this investment. Everything from how to think about diligence for a startup, to the process of investing (e.g., how preferred equity docs work), to how to be most helpful to the founders once the investment is made.”


Sapna invests $50K on average for a seed round with a $5M valuation or less, and makes follow-on investments as well. She invests mostly in NYC area and teams with female founders or with underrepresented minority founders are her preference. Sapna is also a member and on the Board of Directors of New York Angels where she brings deals to and invests in deals that others bring in as well. She also has relationships with early/seed stage VCs that she brings deals to if it fits their criteria, such as Brand Foundry, Corigin Ventures, Grace Beauty Capital, 645 Ventures, SWAT Equity, Black Jays VC, Lattice Ventures, among others.

“I am more helpful to my portfolio companies when they are in my sweet spot in terms of industry focus (retail tech, e-commerce), so I am more and more focusing on those sorts of investments…I believe there are still significant opportunities for retail, and I believe that retail and shopping are going to look very different 20 years in the future. Those are the kinds of startup opportunities I’m looking for.”

Sapna is carefully watching these futuristic trends, even those that seem early.

“AR/VR is definitely getting a lot of hype, but I think it’s still pretty clunky in the way it’s used in retail/shopping. Visual search is getting more interest, and there are a number of startups working on creating accurate visual search for fashion that helps consumers shop. Again, it’s early days but something I’m keeping an eye on. Recently, I’ve been looking at companies that take the friction out of e-commerce and mobile commerce — and I invested in Reply Yes, which is doing this via a seamless chat/messaging service for brands with fans. Right now, I’m also looking for startups that bring the joy of product discovery back to e-commerce and mobile commerce — particularly a user experience that isn’t an infinite scroll of millions of SKUs.”

Sapna splits her time between seeing new entrepreneurs (~40–50 a month) and helping existing portfolio companies. Her philosophy when meeting startups and entrepreneurs is that even if she’s not interested in investing, she tries to be helpful in at least one, concrete way. That could be anything from an intro to potential hires/consultants/advisors, to feedback on improving the deck or financial model, to sending them resources that can help them in the fundraising process.

When it comes to her portfolio companies, Sapna likes to be actively helpful, especially before the next round comes up — whether on strategy, introductions, hiring, and more.

“I’ll try to stay up to date on the company’s progress and readiness to raise another round. I do everything from making intros to investors, helping to shape the pitch/deck, reviewing financial models, reviewing and helping to negotiate term sheets and more…”

I’m Not Mr. Shah!

Sapna looks for founders with domain expertise and a passion for solving the myriad of problems that retailers face. It must be a big enough problem to solve, a large market size, a solution that customers will pay for, a unique competitive advantage and some level of traction. She says that a great competition slide is probably the most vital part of an investor deck.

“This can be tough for a lot of entrepreneurs, as they don’t really like to include all possible competition that exists — but it’s critical to understand the landscape in evaluating any business.”

Sapna sources investments in a variety of ways — demo days, pitch events, conferences, accelerators, intros from others and angel groups. The best way to reach her is a warm intro from another founder or investor, especially if that person is knowledgeable about your business. If you’re a founder from one of her alma maters, she will always take a look at your startup. She does respond to cold emails either through her website or LinkedIn if they are well-researched and relevant and makes a particular effort to accept cold emails from female founders and underrepresented minorities.

“I often get cold emails from founders, which is fine with me. In many of those instances, they have clearly gone to my website to learn more about me (and they’ve referenced that in the email), but still address the email to Mr. Shah. It’s pretty clear from my bio/photo that I’m not a Mr. — and this just makes me less likely to view that startup as a potential investment. If you can’t do your homework on me before sending an email, why would I think you’ve adequately researched and thought through your startup? Also, don’t bombard me on multiple platforms at once (e.g., cold email + LinkedIn email + Twitter DM + Facebook outreach + AngelList). That doesn’t happen often but it’s annoying when it does!”

Sapna’s Best Advice for Fundraising

  1. Understand the Process Before Starting — There are a lot of great articles, blogs and resources that you can review to understand best practices in fundraising, along with tools that others have put together that can save you time. I have a list of these on my website, but there are plenty of other great sources out there. Once you understand the process, it’s significantly easier to go out and fundraise.
  2. Get your Diligence Materials Ready — Be ready to make the process go quickly and smoothly. Have not only your deck ready to go, but also a blurb, an executive summary, a realistic and thoughtful financial model, description of technical architecture (if necessary), team bios, any IP/contracts, etc.
  3. Know your Potential Investors  — make a list of who you’re going to target, make sure they invest in your sort of business/stage. Understand what they look for, what other companies are in their portfolios. Keep a spreadsheet to track all conversations. If you get a no, find out why and track that — it could be helpful in the next round. Find warm intros as much as possible.

About Becoming an Entrepreneur Again

Sapna says that she’s always thinking about becoming an entrepreneur again. While she hasn’t quite found the right fit yet, it’s definitely on the table for the future.

“When I was in investment banking, my Managing Director told us: “it’s a small world and a long life” which has resonated with me to this day. It has always reminded me that keeping in touch with people even when they’ve said no to you in the past (from an investment, hiring or other perspective) is useful because things do change.”

If you think you are a good fit for Sapna, you can reach out to her via Twitter @redgiraffe or through her website:

Also shared on The Mission

About the Author

Donna Griffit

Donna Griffit is a Corporate Storyteller and Pitch Alchemist for startups who, over 14 years, has helped hundreds of startups and VC’s around the world raise hundreds of millions of dollars by creating stellar pitches and investment materials that compel and propel.

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