Event Recap: Founders Tell All, San Francisco

Event Recap: Founders Tell All, San Francisco

Third Wave Fashion descended upon San Francisco for their second fashion tech meetup in the Bay Area entitled “Founders Tell All” in an intimate setting provided by sponsor Orrick. One-on-one interviews conducted by none other than founder (and gifted orator), Liza Kindred, had fashion tech pros in the hot seat sharing their experiences and dropping knowledge to a diverse crowd comprised of entrepreneurs, brands, media, investors, lawyers and engineers. Speakers for the evening were: Brian Sugar, CEO at PopSugar, Lindsey Guest, CEO and Founder at Beauty Army, Aubrie Pagano, CEO at Bow & Drape, Colin Stuart, Co-Founder and CTO at Betabrand, and Stephanie Palmeri, Principal at SoftTechVC. 

Founder’s Story

The first guest of the evening was Brian Sugar, CEO at PopSugar, a digital destination for women combining lifestyle content and commerce headquartered in San Francisco with satellite offices in Los Angeles and New York. The company has expanded internationally and currently has 303 employees on staff. Originally positioning to be the next Condé Nast of the publishing world, PopSugar has since evolved into more of a cable company. Think “ESPN for women” where the sport is shopping.

Brian did not graduate from college. Instead, he started his first company during senior year. In 1994, upon first seeing the internet, Brian knew he needed to build a website. Armed with a business plan and college tuition money from his father, Neptune Interactive was born. During this time Sugar sent CD-roms to retailers such as J.Crew, Land’s End and Abercrombie & Fitch of what their websites should be like. Brian proceeded to spend five years at J.Crew and was recruited to start Bluelight– a combination of Kmart, Yahoo and Martha Stewart– which had its sights set to take on Amazon. The company raised and blew through $160M in 18 months. Questioning if the internet was over in 2001, Brian did what any entrepreneur would do and started his next company, 2Wire, which was sold to AT&T. In 2005, Brian’s wife, Lisa, started blogging and the two were encouraged by Om Malick of GigaOM to take on Condé Nast. While the publishing magnate recently launched Condé Nast Entertainment for branded video content, PopSugar began using video in 2009 with a purchase of LA-based company, Shopflick. The company now shoots live shows in San Francisco, Los Angeles and New York generating up to 220,000 viewers on a daily basis.

While discussing the generation gap and their children having no concept of dial-up internet and TV channels, the conversation turns towards the importance of family and how being a family man has affected Brian’s entrepreneurship. Startups are like families. Treating people with respect and company culture is of great importance and critical to success.

With the merging of content and commerce, maintaining journalistic integrity is a hot button issue. PopSugar editorial is kept separate from the company’s commerce component, visual search engine ShopStyle. Brian notes it is hard to get people buying contextually while reading the latest about the Met Gala and feels the site ultimately needs to be a destination for commerce. Capital raised in 2006 was to be repaid through advertising and ShopStyle was part of the original strategy to get close to the transaction without taking in inventory.

When asked for advice for budding entrepreneurs, Sugar recommends looking at yourself and understanding what you are and aren’t good at. Equally important is recognizing others’ strengths and creating the best team for attacking what you want.

Customer Acquisition

Lindsey Guest always knew she wanted to be an entrepreneur and was inspired by her mother who was a lawyer. She obtained a masters in Integrated Marketing and proceeded to work with Pepsi where she fell in love with branding. An obsession with the beauty industry led her to the Bobbi Brown School where she became a makeup artist and learned the trade of the business. As CEO and Founder of Beauty Army, Guest sought to revolutionize the beauty industry and didn’t want consumers to have to sift through thousands of products. Beauty Army provides technology that matches consumer attributes to product attributes in seconds.

The company has been live for 16 months and heavily engages in social media for customer acquisition. Hosting contests and integrating share features are a few ways to get started with little to no money. Lindsey recommends not burning through money on your customer acquisition strategy too early as the company might not be ready for all the attention.

Beauty Army is leveraging the power of YouTube and acquiring customers through haul videos. People find the product engaging and are sharing their finds through third party videos and referral links. The company also uses Facebook in their strategy, sharing functions are enabled on each product page and contests are ran using the Wildfire app. Lindsey sees Facebook as a customer service tool since people readily express their views on companies’ walls. While Facebook is used to acquire new customers, Twitter is used to engage existing customers, and their Pinterest account is primarily used for pinning onto beauty boards and running contests. Subsequently, Beauty Army’s Instagram account provides an insider’s view to the company. Lindsey’s advice prior to starting social media: Make sure you have something to say and make your content engaging.

Public Relations

Donning a handpainted “cardimono” (think cardigan/kimono hybrid) available on Bow & Drape, CEO Aubrie Pagano introduced the first platform offering customized fashion for women to design their own clothes. The garments are produced in New York and the company handles all aspects of the production cycle from design to delivery.

The company’s PR strategy begins with Aubrie asking what is the story Bow & Drape wants to tell. For her it is all about storytelling and connections. Much like the slow food movement, consumers want to know where materials are sourced and how their garments are produced. Bow & Drape capitalized on manufacturing in New York and tauted craftsmanship during the company’s launch five months ago while they had people’s attention. When asked about getting PR after the launch, Pagano continued to stress storytelling and suggests thinking about personal stories that are relevant. Additional options include capitalizing on timely news events and pushing articles which apply to your company.

After graduating from Harvard in 2008, Aubrie landed at Fidelity Investments for three years. Not “fitting in” in the financial world led Aubrie to become a fashion apprentice where she traded her Skillshare knowledge to gain insight about the design business. When unable to find an outfit for a wedding, Aubrie made her own dress and received multiple compliments. Women wanted to know how to make affordable one-of-a-kind pieces for themselves and so began Bow & Drape. Liza noted a number of made-to-measure companies exist for men but the same can’t be said for women. Seeing that only 2% of garments are domestically produced, Bow & Drape incorporates being made in the USA into their marketing. The company provides video to show insight into sample rooms and to document the artisanal qualities of their clothing.

Social Media

Betabrand launched in 2004 as “Cordarounds” and was started on a whim. The brand currently offers over a hundred different items for sale with each product having its own unique backstory. No traditional marketing budget exists and the company is run like a blog with new product being conceived daily. Working with a short four month cycle from conception through production, the majority of the company’s manufacturers are housed in SOMA due to tight turnaround schedules and the high frequency of sending goods out to factories. Betabrand pays particularly close attention to the internet and creates clothing which speaks to those communities.

Co-Founder and CTO Colin Stuart noted a recent move into the company’s flagship location on Valencia Street in the Mission District. When asked if he forsees a social media shift with their brick-and-mortar addition, Colin responded the store is an extension of their site. The company already employs user-generated content onsite and now an opportunity exists to create content offline in-store. The Valencia Street flagship is also seen as a think tank to source ideas from the community and collaborate with other creatives. While people are incentivized through profit-sharing, the desire to contribute and create is also rewarding.

Colin’s engineering career includes stints with Microsoft and i-drive. The actor-slash-producer then moved to Los Angeles to work in the entertainment industry. Upon returning to San Francisco, he teamed up with Betabrand CEO, Chris Lindland, and the rest is history.

Betabrand uses Facebook for customer acquisition and interaction. Caption contests aid in gaining new customers. Twitter is mainly used for customer service. Creating interesting content gives people something to talk about and Betabrand has no shortage in this area. The free-spirited vibe at the heart of the company extends throughout their campaigns and company newsletter, which has one of the highest opening rates in the industry at around 50%. With a mix of branded and user-generated content, Betabrand’s stories sell product and bring people to their site and flagship location.


As Principal at SoftTechVC, Stephanie Palmeri actively invests in seed stage companies. The SoftTechVC portfolio includes companies such as Kaboodle, Poshmark, Fab and True & Co. She had a brief stint as a buyer at Lord & Taylor before landing at Accenture. After four years in marketing at Estee Lauder, Stephanie attended Columbia Business School. Fresh from her move from New York to San Francisco, she met Jeff Clavier of SoftTech but he didn’t initially hire her (check out this letter by Jeff introducing Steph to Soft Tech.) With some additional communication and persistence, Stephanie was in. Her combined point-of-view and experience in the commerce space proved to be an asset in the burgeoning fashion tech scene two years ago.

When looking at the space now, Stephanie see roadblocks for certain companies such as ShoeDazzle and Beachmint which require inventory. Investors recognize these companies take more time and patience to see the desired growth but they must also take into consideration who will continue to fund the startups after the seed round. Asked if “Series A crunch” exists, Stephanie answers yes since so many companies are entering the space and creating a lot of noise resulting in fewer competitors getting funded. Palmeri advises having really strong metrics and differentiating yourself from the crowds which are becoming overly saturated. She cites Poshmark’s mix of mobile, photos, social and commerce as a prime example of bringing something unique to the table. The shopping app isn’t just about commerce, it is also about the community it has created. She recommends having a story that stands out and keeps customers coming back for more. Metrics reviewed during the seed round include (numbers may vary) being in the market for a few months with traction, being live and letting people in gently, showing month over month growth and repeat customer behavior.

Stephanie is currently interested in B2B commerce and the challenges companies face in fulfillment and merchandising. She is not investing in anything that competes with her current portfolio companies. As a consumer, Palmeri would like truly personalized shopping. As an investor, she wants to see merchandising problems solved. Stephanie provided the audience with her two pitching pet peeves: Instead of taking a long-winded approach, summarize the problem you are solving in 1-2 sentences and lead the conversation with the statement. Also, when attending pitch meetings, refrain from bringing advisors, or what Stephanie refers to as the “creepy old dude”, which could make for an awkward situation. Her suggestion for connecting and getting in touch is through warm introductions. Look into who she knows and, more importantly, who she respects.

At the end of the evening, the resounding key messages included know your strengths, respect others, clearly define the brand voice, tell stories through engaging and compelling content, and differentiate yourself from the competitors.

Avelinda Garcia is principal at Superstylin* specializing in fashion consultation, creative project management and content curation. Her career began at Women’s Wear Daily and W and for over a decade she worked for ready-to-wear designer CHAIKEN. Miss Garcia is currently an adjunct professor at the Art Institute of California in the Fashion Design and Fashion Marketing & Management Departments. You can follow her here. 

Third Wave Fashion has been your fashion tech think tank since 2011. We publish the first ever printed fashion tech magazine, Third Wave.  Follow us on Twitter or subscribe to our newsletter to stay on top of the latest in fashion tech + wearables.

Image via TWF.