Wisdom Shared From 78 Tech Trailblazers

*****Also posted to Medium.

Three weeks ago I graduated from the growth track at Tradecraft. It’s a three month program that prepares individuals for traction roles at high growth startups. (See my post How Twitter Changed My Life on my decision to join Tradecraft.)

One of my favorite aspects of the program was the five mentor sessions each week. I love meeting new people, learning about their backgrounds, and the decisions they’ve made that led to where they are today.

I also sent out cold emails to people with backgrounds I’d like to emulate. These cold emails resulted in over 50 coffee meetings. I also met dozens of people through attending the Brit + Co Re:Make Conference and Women 2.0 Conference.

My lack of fear sending cold emails stems from my background of journalism at Convent of the Sacred Heart High School. My teacher required we have three different sources for every story, meaning that I’d have to speak with dozens of people to get my quotes.

Since I’ve learned so much over the past three months from people I’ve met, I wanted to share a few takeaways. Here’s the outline:

• On Growth (Josh Elman, Sean Ellis, Brian Balfour, Gustaf Alstromer, Zack Onisko, Melody McCloskey, Laura Klein, Ada Chen Rekhi, Ryan Delk, Arjun Naskar, Katelyn Watson, Aarthi Ramamurthy, Danny Moy, and Jordan Koene)

• Share Feedback (Maya Grinberg, Cathy Vigrass, Randi Zuckerberg, and Krithika Muthukumar)

• On Networking & Friendships (Brit Morin, Dave Morin, Julia Hartz, Hiten Shah, Alexander Tibbets, Amanda Pouchot, Perri Blake Gorman, and Frederik Hermann)

• On Leadership (Xochi Birch, Dave Morin, Doug Landis, Sean Sheppard, Misha Chellam, Lisa Falzone, James Proud, Raz Roman, Tristan Pollock, and Erica Brescia)

• On Investing & Fundraising (Dave Morin, Hunter Walk, Crystal McKellar, Victoria Ransom, Pascal Levy-Garboua, Amit Kumar, Jessica Mah, and Thomas Korte)

• How to Approach Learning (Kathy Savitt, Irene Au, Xochi Birch, LJ Kwak, Graham Hunter, John Barrows, Jenna White, Sofia Pessanha, and Shawn Plunkett)

• How Startups Evolve (Danielle Morrill, Roy Bahat, Gagan Biyani, Jack Mardack, Jocelyn Goldfein, Jenny Morrill, Lisa Falzone, John Eagan, Arjun Naskar, and Elena Grewal)

• Advice on Finding a Job (Sam Shank, Jared Fliesler, Sheana O’Sullivan, Russell Klusas, Matt Ellsworth, Elli Sharef, and Lauren Vingiano)

• Be Creative (Cathy Vigrass, Camille Ricketts, and David Nihill)

• On Personal Development (Jared Fliesler, Libby Leffler, Chris Kim, Joshua Scott, Andrea Soto, and Santiago Merea)

• On Being a Woman in Tech (Sheryl Sandberg, Lauren Kay, Mona Sabet, and Sofia Pessanha)

“If you’re offered a seat on a rocketship, don’t ask what seat.”

— Sheryl Sandberg

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ON GROWTH

• The most valuable growth tactic at Twitter was calling people. We asked why they signed up, why they left, and what they are using it for now.

• Find out what the people that keep returning are doing. A reverend started tweeting, and then the congregants felt closer to the church. A clown was using Twitter as a contact management system Tweet this

• I ask users, would they be able to live without this product? Tweet this

• Focus, in any respect — whether it’s a growth strategy, product strategy, or life strategy. Pick something, work on it for a substantial period of time, and reflect on it.

• I am always asking why, why, why. Tweet this

• Best practices can be disproven at any time, and need to be changed.

• It is better to have 100 users that love you, instead of 1,000 users who kind of love you. If you find people who love you, you can work backwards and find out why they love you.

• Think of your product in terms of problems. It is easy to improve things that are already working than to start new things. Tweet this

• What is going to move the needle the most in the shortest amount of time? Tweet this

• Advice from mentor Travis Kalanick, Uber CEO: When I was thinking about my first year of business, he asked about year two and three. How could we cut months to execute the vision? Tweet this

• Watch people use your product over and over again.

• People focus heavily on quant. Know where people are coming out of the funnel, and also why. Tweet this

• For growth connoisseurs, sign up for a bunch of startups and do nothing. See what happens and how the startups respond. Tweet this

• Before when Gumroad sellers made over $1,000, I’d write them a handwritten “thank you” card. Now we send “thank you” baskets when sellers hit sales amounts. Referrals are because people love Gumroad. Tweet this

• Detroit is a loss for Uber. They keep it because people expect to use Uber when traveling. Tweet this

• If you can afford to expand a company, do it. If not, find a way. Tweet this

• Tweet at newspapers about a great article they wrote about your company. They’ll retweet it because it was their article. Then your page views will increase! Tweet this

• Without the customer, there is no product. Tweet this

• Make a few micro changes at the same time to compare different customer responses.

• Specialize your product to the local market. Tweet this

• The smartest person in the room says, instead of developing new content, let’s remove content. Tweet this

SHARE FEEDBACK

• Maya was an early Wealthfront user (and joined when it was called KaChing). She loved the service, and would often send ideas. One day they reached out to her about joining the team.

• Engage in conversations on Twitter with people you want to work with. Then they’ll recognize your name, and hopefully a coffee meetup will be next! Tweet this

• Cathy tweeted at the Sosh founders a few times (without the aim for a job). One time she tweeted a photo of her wearing a Jawbone and a Misfit wearable device, and the CEO of Sosh responded about meeting up.

• Tell your boss if your work isn’t challenging. At Randi’s first job after Harvard, she primarily made photocopies for a year. She finally spoke with her boss, who never realized that she wasn’t being challenged enough. Tweet this

• Stripe is transparent. They -cc a list on every email. This allows them to get input faster and work evolves faster. Advice: get input often and early. Tweet this

• The people who are tweeting at me, I see their faces and we’re building a relationship. Tweeting at people is the new cold call. Tweet this

• While working at Apple, Dave would go into Steve Jobs’s office to chat. No one else would. Tweet this

• Humans need to connect offline to live a fulfilling life. Live experiences have increased in value. Tweet this

• Networking is not about researching a person's background. It's about seeing what they are into now — on Twitter, blogs, etc. Tweet this

• Be a luncher. Networking helps with recruiting, building partnerships, getting VC funding, and having a network also means that you have people to go to when you have questions. Tweet this

• Amanda stressed the importance of having a supporter. She had two great supporters while working at McKinsey, who made intros for some of Levo League’s initial funding. The investors trusted Amanda’s supporters, and knew that she must be amazing since she had their support. Tweet this

• Introductions are great. Social proof is better. Tweet this

• Front load all relationships.

• Study who you want to be like.

• If you don’t have something to offer a person, you can pay attention. Tweet this

• Don’t apply for jobs on job boards. Use your network.

• Build a brand identity around yourself. You are not attached to a company. Build your identity around your full name. Use the same picture across social media so people can recognize you. Tweet this

ON LEADERSHIP

• Xochi was happy she didn’t reach success until her early 30s. By then she had already developed as a person, and the money didn’t go to her head. The day after she and Michael sold Bebo, they saw Forgetting Sarah Marshall in the middle of the day!

• You’ve achieved success when you can deal with a challenge quickly. Tweet this

• Give a meeting schedule, otherwise management will take it over. Provide a recap, purpose, plan, and outcome. Tweet this

• It’s Not About You. Your success is measured by the success of your people. Tweet this

• MBWA (Management By Walking Around). Tweet this

• On time arrival — it matters. Tweet this

• Read books about others who you want to emulate. Tweet this

• Be skeptical about everything. Tweet this

• Delegate tasks.

• No one knows your company better than you do. Tweet this

• I’m constantly taking on and pulling off layers — just like a rattlesnake. I’m shifting responsibilities. Tweet this

• Outsource anything that is not imperative to the business. Tweet this

ON INVESTING & FUNDRAISING

• Tell everyone about what you’re interested in. Dave really likes drones, so he often tweets about them — and gets many inbound offers about investing in drone companies. Tweet this

• It’s a seed period, not a seed round. Tweet this

• Set a timeline for fundraising, just like a product or feature. Tweet this

• Capital is a lagging indicator. Talent is a leading indicator. Tweet this

• When you raise a round, make sure you ask for the amount that you truly need so that you’re not back in the market seeking additional funding every six months. To be successful, CEO’s need to be focused on product and growing their businesses, not on raising money.

• Before, Victoria advised entrepreneurs to bootstrap. In the current environment, she encourages to raise as much, as fast as you can — or else your competitors will!

• I invest in what I know. My goal is to learn more about something I like. Tweet this

• Fundraising is necessary, but not important. Fundraising is oxygen. You need it to live, but that’s not the point of living. Tweet this

• The day you get money from the guy who doesn’t owe you anything is the day you know you have something. Tweet this

• Use a whiteboard to generate ways to make money. Ideas don’t just come to you. Tweet this

• If an investor says it sounds interesting — they absolutely hate you! Tweet this

HOW TO APPROACH LEARNING

• Never refuse knowledge. Someone is giving you a free gift. Few things in life are free. They are giving you the truth that’s important enough to waste their breath. Tweet this

• Don’t hand over your mental real estate. Kathy would ask Marissa Mayer what she thinks about article X about herself. Her response: “I don’t read them. Margaret Thatcher said it put her off balance so she never read them.”

• What are you curious about? As long as you are growing and learning, you will be thriving. The kiss of death is when you are no longer learning. Tweet this

• You learn more from mistakes than you do from successes. Tweet this

• Sales is a science, not an art. Tweet this

•  My big requirement is to work with someone worldclass, so I’ll really learn a lot. During LJ’s last semester of business school, she took Wharton’s most desired course — negotiation with Stuart Diamond. Now she’s working with him.

• (Graham’s response when asking him a question) I don’t know — you tell me! Tweet this

• Have direction on what you want to learn in a position.

• Learning is what you get when you don’t get what you want. Tweet this

• Appreciative inquiry process: Identify what works well right now. Imagine where you want yourself and team to be in the future. Innovate a way to get to what you imagine.

HOW STARTUPS EVOLVE

• I wanted to call BS on what's BS. It's fun to make everyone angry, because then you find out what's important to them.

• You can’t write about rumors and gossip — but you can write about data. Tweet this

• Process is like salt. A little bit goes a long way. I say, have as little process as necessary and then add more. You want the process to emerge with the complexity of a company. Tweet this

• Sprig started with ordering through Eventbrite, a physical map to pinpoint orders, and manually texting customers and drivers about orders. Tweet this

• Jack was Eventbrite’s first Head of Marketing. He noticed events being indexed, which led to the creation of the directory. They allowed custom vanity URLs.

• The Facebook web to mobile transition took a year. It wasn’t a coding issue, it was challenging because of the culture change. Tweet this

• Prioritize. Jenny wishes they improved upon some of the more basic tasks at the beginning, such as having high quality photos.

•  Interviewing people is a way to get an idea. Don’t just wait for an idea to come — go after it. Tweet this

• Pinterest tried to re-engage non-active users with a sound notification. Surprisingly, it had no effect. Tweet this

• NYC was the fifth city Homejoy expanded to. Their cleaning caddies fit through San Francisco's BART, but we learned the hard way that they didn’t fit through NYC’s subway! Tweet this

• People are afraid about writing anything negative, so Airbnb recently launched double blind reviews, to test if people would submit more reviews. You can only read your guest/host’s review after you have written yours. As a result of the change, review rates have skyrocketed because people wanted to know what other people wrote about them.

ADVICE ON FINDING A JOB

• Take a risk, even in a downturn in the economy. Tweet this

• It doesn’t matter if a company is hiring. If you want to work there, reach out to the founders and CEO. Offer to clean the floor or help in any capacity. Tweet this

• Be visible. Work on what the CEO cares about. Your job is to make your boss’s job easier. Tweet this

• When you are no longer learning from those who you are working with, it is time to change roles. Tweet this

• If you want to be an expert at growth, you need to study under a growth expert. Tweet this

• Create content around a subject area where you want to work. Tweet this

• Do not focus on the specific job, company, title, or salary. They don’t matter. What matters is who will teach you when you start learning. Interview your boss. Tweet this

• If you find someone and you believe in their mission — it doesn’t matter what your role is. I followed that advice, and it’s been fabulous. Tweet this

BE CREATIVE

• Cathy waited in line for the opening of Apple in London, and her photo was in the papers. So when she sent her thank you card after interviewing at Apple, she included the image!

• The most effective pieces of marketing shows you how life could be. Tweet this

• Add comedy to presentations to make them more memorable. Tweet this

ON PERSONAL DEVELOPMENT

• If you’re not drowning, you’re not working hard enough. You just have to know when to get out of the pool. Tweet this

• People have to know you well to give you good/useful advice. Tweet this

• Always ask for feedback. Tweet this

• Don’t think of those above or below you too much. It is so easy for success to come and go. Tweet this

• Be humble, do your best, and go the extra mile to support the people who hired you. Tweet this

• Every time I would fail, it made me competitive. It made me valuable. It made me successful. Tweet this

• Keep a journal. It will be fun to look back on after a year. Tweet this

ON BEING A WOMAN IN TECH

• There was a study done that showed it is easiest for attractive men to get funding, then unattractive men, then unattractive women, and lastly, attractive women.

Most investors are male, and not all — but some — do treat female founders differently from male founders. When most seed fundraising is based on initial gut instincts, these subconscious biases against women can make fundraising a lot harder.

Lauren had to turn down funding because of inappropriate behavior.

• Women get more and better promotions within three years if they are active in 2–3 women’s groups. Tweet this
But if women aren’t active in any groups, or if they are involved in ten groups — then it’s not likely they’ll be promoted.

• The problem isn’t about men vs. women — it’s about business vs. tech. Tweet this

Thank you to everyone who answered my cold emails, and met with me to share your stories and answer my questions. The list goes on for people I’d like to meet, but unfortunately time is limited.

Work, Work, Work Some More

The perspective of Jared Fliesler who’s had a career from start-ups to venture capital — even before turning 30

Most of us wish there was a formula to achieve success. While this isn’t the case, Jared Fliesler, General Partner at Venture Capital firm Matrix Partners, shared his personal formula with Tradecrafters. Given that he has already achieved success at a real estate investment company, Slide (a social entertainment application publisher acquired by Google), been Google’s youngest Director of Product Management, Square’s VP of User Acquisition and Business Operations, and now at Matrix Partners — all before turning 30 — Jared has definitely earned credibility.

The Beginnings

Jared was one of ten writing food reviews on Yelp while a student at the University of San Francisco in 2003. Being a member of the “Yelp Elite” was his virtual currency, as everyone wanted to be his +1 to Yelp’s sponsored college parties.

After graduation, Jared began his career at a real estate investment company. He ran account sales for Northern California, Oregon, and Nevada, and discovered he had the same number of clients, yet half the salary, as a rep with the same role based in Los Angeles. Jared was denied a raise because he had fewer years of work experience. He realized the company’s structure valued time spent over quality and efficiency. No matter how hard he worked, he couldn’t advance quickly. This gave him no incentive to work hard, and didn’t reward his work ethic — so he decided to search for a new opportunity.

How He “Made It” in Tech

Jared’s tips for achieving success:

1. Work harder than everyone else. Be the first to respond to Saturday email, cancel trips, and work late on Friday nights.

   • Jared tells his partner, friends, and family that work comes first. As much as he would like to spend time with them, his work is more important.

2. Be in the office. It’s easy to come in an hour earlier and stay an hour later. You’ll stand out. Your boss will think of these moments come evaluation time.

   • He mentioned that the startup culture has changed since he joined Slide (acquired by Google) in 2007. People are showing up to work later and leaving earlier. They aren’t working as hard as they used to, which is negatively impacting company pride.

3. Always ask for more work. “If you’re not drowning, you’re not working hard enough…You just have to know when to get out of the pool.” Surround yourself with people who inspire you.
    

4. It doesn’t matter if a company is hiring. If you want to work there, reach out to the founders and CEO. Offer to clean the floor or help in any capacity.
    

5. Be visible. Work on what the CEO cares about. Your job is to make your boss’s job easier.

   • At Slide, Jared worked on competitive research, and sent it to his boss. It was forwarded to everyone, and then the CEO read it. People started to request meetings with him to discuss his findings. This led to him naturally assuming the role of Head of Growth.

6. Find a way to relax.

   • Jared’s secret is going to the Indian Springs Resort in Calistoga for a mud bath.

7. The more that you can be the glue that sticks the growth, sales, and product teams together, the more successful you will be.

To achieve success, set clear goals and work relentlessly to achieve them. Jared’s goals clearly include excelling in his career, so he has dedicated his life to work. His career has skyrocketed, and we are left to wonder what more Jared will accomplish.

How Twitter Changed My Life

When I graduated Scripps College mid-May with a B.A. in Economics, I was set. I had been signed on for eight months to join Nestlé’s three-and-a-half year finance rotational program in July. I never expected what would happen next.

Nestlé’s finance rotational program is designed as a career accelerator, so graduates can quickly climb the leadership ladder. Many of my friends and classmates had accepted investment banking and consulting offers, and I felt that I needed to have a job secured as well. While this program can be an ideal path for young professionals with career ambitions within a single company, I wanted to work in tech. I’m fascinated by how disruptive technologies are changing the world in unimaginable ways. I felt that the skills acquired at Nestlé wouldn’t transfer to the innovation of today’s fast paced technology startups.

Then on May 29 I attended an event with the female founders of Eventbrite, ModCloth, and One Kings Lane. After the event I spoke with Eric Koger, Modcloth Co-Founder and CEO, and mentioned my dilemma of having accepted a position with Nestlé, even though I wanted to work in tech.

Eric advised that I begin my career in the tech sector, instead of planning to transition to the industry after Nestlé. Speaking as an executive of 500 employees, he explained that he would rather hire someone from a no-name technology company than from Nestlé, because it is difficult to make the industry transition. He understood wanting to have a halo on a resume, as Nestlé is one of the world’s largest companies — but thousands of others already work at Nestlé.

It was difficult for me to pass on the opportunity with Nestlé without a Plan B. But after speaking with Eric, I realized that I should pursue my passions instead of following a conventional path. I am a risk taker, and that is not the culture of a large established conglomerate. Additionally, upon reflection, my favorite part of interning at Nestlé was forming relationships with my superiors by having lunch with someone different every day: from first year analysts to the CEO and CFO — which I would have missed through working at my assigned Bloomington, Illinois factory.

Eric’s insight left a big impression on me, so four days later, the day before embarking on a one-month trip to Ireland (probably my last extended vacation before retirement!), I called Nestlé to inform them I would no longer be joining the company. I had no Plan B. This was slightly terrifying yet exciting at the same time.

I started my job search process juggling job postings and Linkedln connections — while organizing everything in Excel. Then one tweet by Gagan Biyani, Sprig Co-founder and CEO, changed everything.

I Googled Tradecraft, and soon submitted my e-mail address and resume. During my interview rounds over Skype and Google Hangout while in Ireland, I realized that Tradecraft would teach me the skills to jumpstart my tech career. Without Tradecraft, I was just another recent college grad looking for a job. Tradecraft would provide me with the mentoring to learn what aspect of tech I’d like to enter, and help me have a larger impact at a start-up from day one.

Many people view social media as a waste of time. But Twitter is a way to gain insights into thought leaders and regular folks who you wouldn’t have the chance to interact with ordinarily. By reading their tweets, you can find out about news and opportunities that you otherwise wouldn’t be aware of — that’s how I found out about Tradecraft.

I arrived home to San Francisco on the 4th of July, and started Tradecraft three days later. Over the past five weeks I have gained insights from start-up founders, growth marketers, sales executives, and design leaders. I look forward to my next seven weeks at Tradecraft of acquiring analytical skills to grow a company, in addition to personal and professional development — all while spending time with other like-minded individuals with similar aspirations.

I am writing all of my lessons learned, from others and myself, in a journal so I can continue to reflect on them as I embark on my career. I will share highlights from these conversations in one cohesive post when I graduate Tradecraft. But for now, my most important lesson has been to follow my instincts.