The ability to be flexible is absolutely vital for successful entrepreneurs.

 

For someone still early in their career, Ashley Brasier has racked up an impressive list of career accomplishments, including making critical contributions to the development of some of the last decade’s top companies. From the earliest age, Ashley has been fascinated by the process of developing new products, services, and business models. As a child, Ashley was captivated by her father’s architectural work and loved to sit at the drafting table with him. Today, while Ashley has pivoted away from architecture, she is at the forefront of architecting the future of business.

As an integral member of the investing team at Lightspeed, one of the most broadly diversified venture capital firms in the world, Ashley gets to use both her extensive knowledge and deep love for creating new products every day. As a partner with Lightspeed Venture Partners, Ashley has brought her unique perspective and striking knack for both spotting and creating trends to bear. She has also helped to diversify Lightspeed’s operations further, providing keen insights into the female-driven consumer retail market, the single most significant driver of economic activity in the United States.

Although modest about her accomplishments, Ashley has worked for a veritable whos-who list of power players in the world of cutting-edge tech finance. Fresh out of Duke University, she went to work with consulting giant Bain & Company. While there, she learned the value of not just possessing both foresight and insight but also of using sophisticated tools like economic modeling to help shape actionable business intelligence.

From there, she was recruited by Thumbtack, a tech startup that sought to connect professionals with local clients. Ashley helped to build out Thumbtack’s Events and Weddings platform, helping to propel it into becoming one of the premier online marketplaces for hiring events-related services.

After graduating from Stanford Business School and leaving Thumbtack, Ashley sought new adventures and was eventually linked up with Lightspeed Venture Capital where she remains today.

At Lightspeed, Ashley has been delighted by the opportunity to continuously work with early-stage startups, meeting the challenges and living the thrill that she and other entrepreneurs know can only come from exercising their creative genius for the good of all.

Where did the idea for your company come from?

When I left Thumbtack to start business school at Stanford, I didn’t feel that my work at Thumbtack was done. I loved my job at Thumbtack and wanted to find a way to continue working, while also attending school. While my category management job required daily touchpoints (and thus wouldn’t be a fit for part-time consulting), the marketing team had a number of relevant research and strategy projects that were a fit. These projects enabled me to work on real-world problems, while simultaneously immersed in the largely theoretical world of academia. I loved this balance and continued consulting for the following two years. Consulting was a natural fit, given that I had started my career as a management consultant with Bain & Company.

After a few months of consulting exclusively for Thumbtack, a few former colleagues heard about my projects with Thumbtack and introduced me to startups looking for help with growth strategy. What had once been a side-project turned into a full-time job upon graduation from business school. During this time, I primarily worked with two startups on growth strategy – Fundbox (fintech) and BetterUp (wellness). The projects afforded me the ability to make a steady income, while simultaneously working on some business ideas (and ultimately recruiting for VC jobs).

While I’ve since stopped the consulting work, given my full-time commitment at Lightspeed, I absolutely love the opportunity to work with our portfolio companies on strategy projects. My expertise is in growth strategy – getting companies up the hockey stick in a way that is cost-effective and affords long-term sustainable growth.

What does your typical day look like and how do you make it productive?

My day generally starts around 6:00 AM. I’m not a morning person, but have learned to become one, as the morning offers a brief window of peace and quiet before emails fire-up and meetings get going. Mondays are especially early for me, as I commute down to our office in Menlo Park for the investment committee meeting with the full Lightspeed Partnership. While an hour-long uber ride isn’t always something to look forward to, one unexpected benefit is that I have been able to witness some pretty amazing sunrises from I-280 (the scenic highway connecting San Francisco to points further south).
Mondays are my favorite day of the week, as I get to reconnect with colleagues, learn about new investment ideas, and pitch my own. To avoid traffic on the way back to SF, I usually schedule dinner with friends in Palo Alto. This is a fun way to meet up with business school friends working in the South Bay whom I wouldn’t otherwise get to see up in San Francisco. I’m always inspired by what they’re working on – from monetization at Google Play to starting a personalized skincare company.

I am generally based in San Francisco during the rest of the week, with the exception of trips to New York to visit portfolio companies or trips elsewhere to visit with entrepreneurs. While in San francisco, I spend most of my time at Lightspeed’s office in SoMa. I love this neighborhood, as it has a number of quiet coffee shops and cozy lunch spots. It’s also a neighborhood I’m familiar with, given that the Thumbtack office (my former office) is just a few blocks away.

Each day in San Francisco is different, though there are some well-worn routines that I tend to follow. For example, on a day choc-full of meetings, I like to start the day at a coffee shop that also has a lunch menu (e.g., Vive La Tarte) and end with meetings in the office. If I’m spending the day running around from one spot to the next, it’s nice to end at The Assembly, given that they offer both a large coworking space and workout classes that start around 6PM.

The majority of my meetings are with entrepreneurs. Some meetings are introductory meetings – a chance for the entrepreneur and I to get to know each other outside of their fundraising cycle. Other meetings are explicit pitches – a chance for me to learn what the entrepreneur is working on and hear how investment dollars would help them reach the next step. Outside of new investments, I also spend a substantial amount of time with existing portfolio companies.

While each day is different, the one thing that is consistent is that my schedule is generally packed with meetings and ends with some self-reflection ‘me’ time. I started journaling during my time at Stanford and find that journaling affords clarity of thought and peace of mind. Similar to meditation, journaling gives me the opportunity to examine and organize my thoughts. This practice has helped me live my life in a more intentional and purposeful way, as I am better able to identify my priorities and determine how to pursue them.

How do you bring ideas to life?

I grew up wanting to be an architect like my dad. Accordingly, I attended several summer camps for young designers and one consistent refrain was “measure twice, cut once.” To me, prototyping affords the opportunity to measure twice, as you can test and iterate on ideas before pulling the trigger. While I’m no longer building physical prototypes in my work as an investor, I find that prototyping also applies to ideas. For example, when identifying a new industry or area to pursue, I often create a framework to organize new learnings. The framework evolves as my learning evolves, given that the framework is hypothesis-driven and can be updated with new insights.

The ability to keep things flexible and to enable yourself to pivot is of critical importance as an entrepreneur. One of my favorite sayings is ‘fail fast and iterate faster.’ While this may seem simple, in practice it’s easy to get bogged down by sunk cost, sunk time, and our own pride in what we had once thought was the right answer. The entrepreneurs I admire the most are those that are able to pivot. It’s these entrepreneurs that ultimately create the best product, as they put the evolving needs of the customer first.

What’s one trend that excites you?

The Boomer generation is hitting retirement and by 2033 there will be more seniors in the US than children. I’m fascinated by this demographic shift – and excited to see how this shift sparks innovation in products and services meant for the older demographic. One element of this shift that presents a huge opportunity is the increasing propensity for seniors to age at home, instead of in a nursing home. This shift is driven by a number of factors, including both individual preference and an increase in medicare and medicaid benefits for home-based care.

I believe we will see innovation in three key areas – financial services, in-home IoT technologies, and care services. Financial services is a key area for innovation, as the majority of boomers haven’t saved for retirement. Furthermore, aging at home means there’s a need for financing solutions to unlock value from the home, as a boomer’s wealth is often tied-up in their home. Several innovations are already starting to surface, including reverse mortgage solutions and co-living arrangements.

Aging seniors are already starting to use devices like nest cams and smart locks to enable greater monitoring and care. However, I think we will start to see senior-specific IoT solutions that offer effective, yet minimally invasive monitoring technologies – especially for those with alzheimer’s and dementia. These technologies will primarily promote in-home safety, but could also offer opportunities for remote companionship and care.

Lastly, seniors aging at home will increasingly need in-person help from caregivers. I believe we will see an expansion of at-home care offerings, as well as a higher standard of quality and greater price transparency as offerings become more competitive. In order to win in this space, startup teams must be intimately familiar with the daily needs of seniors and must be willing to adapt their offering as new technologies and regulations are implemented.

What is one habit of yours that makes you more productive as an entrepreneur?

I’ve always had a natural knack for keeping in touch with people. From pen pal relationships in elementary school to text-based check-ins with former college friends, I love hearing what people are up to. Keeping in touch with entrepreneurs is similarly fun and fulfilling – and helps me be a more productive investor, as entrepreneurs are an important source of deal flow. Entrepreneurs are friends with other entrepreneurs and have their ear to the ground on the latest developments in an industry.

While my personal relationships have always been organic and relatively easy to maintain via iMessage and WhatsApp, I’ve found that CRM tools can be really useful to help maintain communication with entrepreneurs. For example, I’ve recently started using Affinity – a CRM tool that enables me to create reminders to check-in with entrepreneurs around planned product launches and other important milestones. These triggered check-ins help me stay on top of the entrepreneur’s business and enable me to offer well-timed advice and support.

What advice would you give your younger self?

I was a pretty loquacious kid, as evidenced by some recently discovered home videos. However, after getting in trouble for talking during reading time a few too many times, I shifted towards the opposite end of the spectrum and was a very quiet middle school and high school student. If I could give advice to my younger self, I’d tell her to speak up – to let her voice be heard and to let herself be seen. It’s a privilege to live in a country with freedom of speech and it’s important to use your voice to stand-up for what you believe in, even at a young age.

Tell us something that’s true that almost nobody agrees with you on.

Guacamole is gross. I know, I know. I must not be a true Californian – and you’re right about that. I much prefer a roasted tomato salsa or jalapeno cheese dip with my Tostitos.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

In high school I worked as a store associate at the bookstore on Duke’s campus. The small office in the back of the shop had a poster with the rules of the game, including “the customer is always right.” Partially out of boredom, and partially out of curiosity, I kept a sheet of paper with me at the register, writing down all kinds of customer observations and insights. I would tally the number of times people asked me certain questions, like my favorite and oddly frequent question: “Does it ever snow in Durham?” I found this odd because there was a poster of a snow-covered campus that hung on the wall behind me, likely prompting this question, but also rendering the question redundant.

This natural curiosity to learn about people and their behaviors led me to take sociology and anthropology courses as a student at Duke, where I learned that what people say and do is often very different. Accordingly, as an entrepreneur I’ve learned that it’s incredibly important to stay close to your customer – to get to know them, observe them, talk with them, and ultimately befriend them. At Thumbtack, I spent several days each month talking with professionals on the platform, understanding their needs and getting their feedback on proposed product improvements. This was time well-spent, as I was ultimately able to make more informed product decisions. Furthermore, these relationships added meaning to my work, as I was building a product with a specific person in-mind. I wanted to help Andrea succeed as a caterer and I wanted to help Dave get more clients for his videography business.

What is the best $100 you recently spent? What and why?

I love to work in a quiet and peaceful environment, which means working on an airplane can be quite difficult – from crying babies to blaring announcements and random dings, there is never a moment to totally tune-out or focus-in. I recently purchased noise cancelling headphones and truly feel the investment has already paid off. With the flip of a switch, the buzzing around me turns into a soft hum and I’m left alone in silence to ponder my own thoughts. This is truly the best $100 I’ve spent in a long time.

What is one piece of software or a web service that helps you be productive?

Apple Podcast App – I try to walk from meeting to meeting as much as possible. The commute from my apartment to the coffee shops in SoMa is about 30 minutes – the perfect amount of time to squeeze in an episode of Oprah’s SuperSoul Conversations or the No Limits podcast with Rebecca Jarvis. I love podcasts that are biographical in nature, as I like to hear how others live their life – specifically, what drives them and how they define success.

Spotify – When I’m really trying to crank out work, especially quantitative analysis, I love a fast-paced soundtrack. My go-to playlists on spotify are Zumba Beats, Happy Hits, and Songs to Sing in the Car. I also love a playlist with strong female vocals – Lauryn Hill, Alicia Keys, and Adele are a few of my favorites.

Ancestry – I keep telling myself I’m going to delete this one, but never do. It’s really fun to learn about family history and also very humbling, as it puts life in a much bigger context and makes me realize how lucky I am to be alive in this moment in time. While I haven’t stumbled on any major family secrets just yet, I did learn that several relatives originated from England – specifically from London’s Holborn district. I also learned that I descended from Cherokee ancestors who walked the Trail of Tears, settling in Oklahoma.

What is the one book that you recommend our community should read and why?

You Are Here: Discovering the Magic of the Present Moment (by Thich Nhat Hanh) – In business school I took a course taught by Leah Weiss called “Leading with Mindfulness and Compassion.” This course exposed me to the works of the buddhist teacher Thich Nhat Hanh and I’ve been hooked ever since. This particular book is a quick and easily digestible read by Hanh, which includes practical recommendations on living more fully in the present moment. Hanh suggests that each new day is a gift and that it is through mindfulness practice that we are able to fully ascertain and experience the happiness and joy that permeates our lives.

What is your favorite quote?

“You may not control all the events that happen to you, but you can decide not to be reduced by them.”― Maya Angelou, Letter to My Daughter

Key Learnings:

  • Don’t be afraid to change things up in your professional life for your academic accomplishments
  • The ability to be flexible is absolutely vital for successful entrepreneurs
  • Financial services are an industry to watch, as they are on the brink of a massive tipping point.