The Spirit of Silicon Valley, with Shaherose Charania

“Connect the unconnected and impact people in a positive way.”

In 2001 when tech wasn’t a hot option for business school students, Shaherose made it one for herself. Her drive has taken her from a student in British Columbia interested in tech to a 2x Silicon Valley founder who’s launched 10 technology products, seen $100M+ raised for her network’s startups, worked with the biggest names in tech, and had worldwide impact. Want to know how?

Go to 1:58 to skip the intro 🙂

• “Try, and if you fail just try again.”

• “Between intuition and data, new ideas emerge.”

In this episode, we talk about:

  • [02:04]What I view as her superpower, the mindset that empowered to go from being a student in British Columbia interested in tech, to a 2x Silicon Valley founder with deep entrepreneurial and product wisdom
  • [16:09]How she learned product management on the job before it was a career well defined in industry
  • [20:27] How startups should leverage data and intuition to make decisions and succeed amid uncertainty
  • [25:47] How to build lasting, incredibly valuable relationships instead of just ‘networking’
  • [32:49]The uncommon advice she gives to new grads on where to start a career in tech, how to choose opportunities, and what advice not to take

And a ton more.

Shaherose reached over 1 million technology influencers and entrepreneurs to advance women-led startups  as the CEO & co-founder of Women 2.0, the first for-profit content, community and events company for women in technology and of Founder Labs, the industry’s first “Lean Startup bootcamp” under the mentorship of Eric Ries, Steve Blank and Ann Miura-Ko. The top 30 pre-seed startups from the Women 2.0 and Founder Labs network have raised over $120M (and counting…).

Through her work, she’s opened up opportunities for top VCs including Sequoia Capital, Andreesen-Horowitz, Google Ventures, and Y-Combinator to connect with the diverse founders in her network. She also established business partnerships with technology companies including Google, Lyft, Microsoft, MasterCard, Salesforce and others.

She started her career off working at 3 venture-backed startups as a Product Manager and Marketing lead at Sequoia funded JAJAH (acquired by Telefonica), Talenthouse and Ribbit (acquired by British Telecom).

Shaherose is currently ‘on assignment’ as an Innovation Fellow at the Nike Accelerator and is an Advisor for, an AngelList sister company. You can say hi to her online as @shaherose on Twitter.


Coming to Silicon Valley? Start with a job at a well-respected company

“If you’re coming to the valley and you’re new, the best thing you’re going to do is take a job first. Take a job at a respected company with smart people. A brand name company, whether it’s Google or Facebook or LinkedIn or Medium, or whatever company you admire. Even if you want to start a company, even if you want to be an investor, whatever your goal is, landing first at a well-known company here will serve you well.

It’ll integrate you into the minds and the network of Silicon Valley immediately. The people you work with, the people you report to, the people that report to you, will be an awesome and exciting network.

The other thing it’ll do is set you up for whatever it is you want to do. Let’s say one day you do want to start a company, now you’ve learned let’s say the ropes of product management, or the ropes of engineering, or the ropes of biz dev at a scaled company, and to aspire to build the company with all that learning. Whatever it is you want to do, I think landing here and joining a well a well-respected company will accelerate where you want to go. And remembering that nothing is forever, right? Going there for two years, or three years, five years, whatever it is that’s right for you.

From there you can pursue the goal and I think that was one thing I wish I had done. I went straight into startups. And that’s great. But startups are chaos. Do you learn how to scale? Do you learn the good habits of — whether it’s product management, marketing, engineering, or business? Maybe you don’t. Because you are running against time, you’re running against running out of money. All these things are happening at once. That prioritizing. Learning sometimes ends up being mostly execution. So that’s my one piece of advice in terms of ignoring advice.”


Building a network: real networking is exchanging value and building trust

Networking — networking for networking’s sake — just creates noise. You make a new connection at an event, you find them on LinkedIn, and there’s no value created. People think Silicon Valley is about this superficial idea of networking. That is false.

It’s about meeting someone who you can give value to. You give feedback on their product because you’re a product manager, and that person is a designer and they give feedback on your product’s user experience. Or one person is an investor and they give feedback on your pitch.

What can you exchange to build a sense of trust? It starts with equal exchange, and supporting each other. It leads to building trust. When trust is built, the real value starts to be created. You realize, “I remember meeting that designer who had great feedback on my product’s user experience — I need to hire someone like that”, “I know someone who’s hiring”, or “I want to start a company with someone like that.” These moments where value can be created come because, over time, trust has been built.

I have probably hired half of my friend circle at any point in my career, and they have also hired me. Some of us have tried to start companies together. Some of us invest together. This sense of trust is critical, primarily in the startup environment, because there’s so much risk.

Focus on five people that you admire, five people you want to hire one day or work with. Become friends. Help each other and guide each other. Bring each other up. The more you can diversify that group, the better. You have diverse perspectives and different networks that they bring to the table.

That’s the essence of Silicon Valley.

How do you become deliberate? Find purpose in your story

“[…] Both that book and that story gave me a vision to move towards. I always would say, I’m here on this earth and my purpose really is to connect the unconnected and impact people in positive ways. And so I sought that out, and I sought out jobs in Silicon Valley startups in Silicon Valley, started a company in Silicon Valley that really fit into that vision. And I think that’s how you become deliberate. You find a purpose in a story that resonates with your values, resonates with the change that you want to see in the world, and it inspires you in good times and in hard times. I just told myself that story. I don’t know where it evolved from. But it just felt right. If I had limited time on this earth, it felt like it was worth my time. And it felt like I would grow from it. I would I would learn from it too. It would give back to me in some way.

With that story is how I made decisions. If I moved to Silicon Valley and met a company but it didn’t fit into this idea of impacting people, connecting people, or connecting things, this theme I kept telling myself, it was a hard no. And that became a way to be deliberate. It became a way to be focused, and it became a way to know that there’s something you haven’t yet achieved and you’re still trying to get there.

It made life less about a job and more about a mission and a purpose. It made it a lot more fulfilling and meaningful for me. Wherever that came from — it was like not one aha moment — it was little things. Reading this book. Hearing the story of this founder. Learning about companies like Google and eBay, and seeing that thread, that same story. It just felt right.”


Alex Norman of AngelList Canada

“Everything I do is aligned in making Canada and particularly Toronto a more competitive space for tech companies.”

From Lehman Brothers to McKinsey, to founding his own company, and now as co-founder at TechToronto and the Canadian partner at AngelList, Alex Norman knows a thing or two about business and startups.

In this episode, we talk about:

  • How he netted $30,000–$60,000 per year as a university student from a side business he started in high school
  • The mindset that’s driven his career from investment banking (Lehman Brothers), to a startup that sold for £400,000,000, to consulting (McKinsey), to founding a company, to TechToronto and AngelList
  • Why he got his MBA (Hint: “It was not for the education.”)
  • The story behind his company and the big mistake he and his cofounders made
  • What he would do if he were starting a company today, and how he’d raise
  • The future of the Toronto tech scene and what it’ll take to build it

“I’m always intellectually curious. I haven’t tried to optimize for fame or money. I’ve tried to optimize for what interests me.” – Alex

On working with startups:

“They [startups] were always short of people and looking for great talent. I had the opportunity to work with startups and do roles that I didn’t have enough age or experience for, traditionally. I jumped there to learn.”

On choosing opportunities: enough rope to hang yourself

“Where is the job or opportunity that will let you grow? And give you lots of responsibility and give you enough rope to hang yourself?”

“Surround yourself with a team you can learn from. I like to get people that are smarter than me, have different perspectives than me. Those can be complemented by online learning. But if you put yourself in that space, you will also find what you should be focusing on.

On SF/NY vs. Toronto-Waterloo
“I think the Toronto-Waterloo corridor has something special going on right now, I think there’ll be lots of large companies, and I think you should stay home. I want all the talent to stay here and I think we’re going to build big things. But I do think there are benefits to getting other perspectives on the world by being part of different ecosystems. It’s a question for each person.

For getting a world class experience, there’s companies [here] like Shopify, Wattpad, Freshbooks, and lots of small companies that are growing quickly that you can learn from, that can be just as valuable.”

On building the Toronto tech ecosystem:

  1. “Put the ecosystem first. If you take care of the community, the community will take care of you.”
  2. “Random collisions lead to collaboration. The thing that builds an ecosystem is random people that wouldn’t normally know each other meet and do something magical. Education and know-how only get you so far, but eventually what build companies are people.”


Quotes edited for publication.

Lessons from a Coach, with Steve Khuu

“It was hard work, and I loved every minute of it.” — Steve

Auto-mechanic, chef, software engineer, consultant, and now coach. I spoke with Steve Khuu, a coach at Flipp, a Toronto tech company that’s connecting consumers with retailers. Flipp is the venture-backed brainchild of former Microsoft engineers.

“Before I got into software altogether, I was a chef and prior to that, I was an auto-mechanic. It doesn’t matter what the trade is. The important thing first is you set the precedence that you want to learn. If you have an attitude that says “I want to continuously improve,” regardless of what you do, you will always be pursued because you’re willing to put that much more effort into it.”

Want to succeed in your career? Go to hackathons.

“I wish I had this when I was in undergrad — going to hackathons. As a sponsor, I love seeing new talent out there. You can be in high school, and come up with something just as brilliant as someone doing their Masters degree. One important lesson: it’s not necessarily about winning. It’s about getting better every time. Winning has its merits, but what I think is more enjoyable is the journey you take and the people you work with to get there.

That’s the true value. The sooner you learn that, the sooner you succeed in your career. You learn to build that intrinsic value with yourself and all these people whom you’ve now enjoyed that experience with.”

On offending million dollar clients:

“As a consultant, this actually happened. If you come with a pre-defined deck to a new client and say, “This is how we’re going to build a solution. It’s going to cost $10 million,” the client’s going to get offended and say, “You don’t know who I am. You’re asking me for money, and we haven’t even started this conversation yet. Who are you?”

This goes back to listening — set the precedence that you don’t know anything. Listen to their concerns so you can address their actual needs, because you’ve now listened to what they have issues with, and what they actually need help with.

Manager vs. Coach

“Go back to my first part time job. It was a tough job, it wasn’t easy, and everyone understood that. The first thing we built wasn’t about building expertise, wasn’t about giving advice. It was trying to set the ground first, being more empathetic, and understanding who is it that I’m working with, not working for.

That’s a big thing for me about a manager vs. a coach. A manager is more about delegating tasks and saying, ‘OK, my checklist is done for the day because these people have done it for me.’ A coach is about working withsomeone and providing that servant leadership to say, ‘How am I going to help this person succeed today?’”

You are not an 8-ball: empathetic coaching

“You get so caught up in the need to give advice that you realize that coaching is not advice giving. You’re not the magic 8-ball that says, “You should be doing this today.” The biggest lesson [at Flipp] was taking a step back and listening. This goes back to being an empathetic type of person. You’ve got to just sit there and listen. Understand who that is you’re spending time with. Build rapport with them, so you know how to engage in an active back-and-forth bidirectional dialogue. We understand that if we ever re-schedule or have to cancel one of our coaching sessions, it hurts us a little bit.”

He gave more tips on what he does to be a great coach at 10:45 in the episode.

What he’s working on today: it’s not about the tools.

“It’s so easy to get caught up learning new tools and building projects with one tech-stack and then going to another. As you progress through your career, you realize it’s not about the tools. It’s about learning about the problems you’re trying to solve. The whole philosophy and foundation behind these problems is pretty transferable.”

He gives a specific example about this at 13:10.


The three books Steve talked about:

  1. Three Signs of a Miserable Job by Patrick Lencioni
  2. Getting Naked: A Business Fable About Shedding The Three Fears That Sabotage Client Loyalty by Patrick Lencioni
  3. Crucial Conversations: Tools for Talking When Stakes Are High by Kerry Patterson, Joseph Grenny, Ron McMillan & Al Switzler

On Self-Starting, with Trevor Sookraj

*apologies for the audio quality – this is when we were starting out. But hey – we shipped.

The hardest thing was telling his friends that he wasn’t coming back. Moving away from his family. For the next year, he’s 2600 miles away in Silicon Valley.

For our first-ever episode of Talk Nspire, we spoke with our friend Trevor Sookraj, a student at Western University, about how he’s helped grow several startups and what he did to launch his career. Trevor’s written a post as an introduction to digital marketing, which we recommend, and you can find here.

Listen to the podcast here.

These were the five big things I learned:

The biggest mistake you can make

“University isn’t about getting you a job.”

Most people wait until they’re comfortable. As a first year, I waited to look at opportunities until I had settled into my classes and schedule and made friends. And I missed a ton of opportunities around me for it. Trevor’s path to interning at Shopify came from meeting someone at a university career fair in first year. The organizers told him he was the only first year they’d spoken to that day.

You don’t know what you can do until you try. Don’t wait.

Go deep on your interests

Whatever it is you want to get good at, there’s a large skill set to master. But that doesn’t mean you have to be overwhelmed. Pick one or two micro-skills (ex. content marketing, or e-mail marketing, for example, if you’re looking at marketing) and go deep on them. Learn what you can. Now you can reach out to businesses and help them with real problems they have.

Boom. You just started.

Talk to people

Before his first trip to Silicon Valley, Trevor cold e-mailed people he wanted to learn from and set up meetings with them. He found that people wanted to help him. People at companies like Google — people we might imagine as being too busy for a chat, or to help out. But the opposite couldn’t be more true.

Andrew Chen is the head of Uber’s Rider Growth team, and investor/advisor at Dropbox, Tinder, and AngelList, among others. He was none of those things ten years ago when he moved to Silicon Valley. As he tells Noah Kagan on Noah’s podcast, he started by reaching out to five people a day.

Start with one. See what happens.

People want to help you. They will — if you let them. Reach out, and start learning.

If you’re comfortable, you’re not learning (Stretch!)

Trevor thought he could get a job based on his internship experiences. But he didn’t stop to rest on his laurels. He’s spending a year in another country, all to learn and get better.

Every step of the way, from the first cold e-mail you send, to the first internship, to your first full-time position, getting better means doing the thing you haven’t done before. All he knew about SQL and programming in marketing was that he had to learn it. So he threw himself into an internship where he’d have to learn it.

“I hit a lot of roadblocks.”

Everyone’s heard of 10,000 hour rule, but Anders Ericsson, the scientist behind it, also describes a less discussed principle: staying on the edge. The edge between what you know how to do, and the skill or ability that’s just out of reach, the thing you haven’t done before. If you’re going to get better, that’s where you have to be.

No growth without stretching.

No gatekeepers — it’s on you

“What’s surprised you the most?”

“How self driven it is.”

There’s no 10-years in industry long hierarchy you have to follow. There aren’t gatekeepers to tell you what you have to learn, or what path to follow for “success.”

Trevor started out with marketing a year and a half ago. He was interested, and he pushed himself to learn on his own time. He reached out to businesses, helped them, had internships, and now he’s working in SF. Push yourself to learn, connect with people, and help them. Put your work on Github, go to hackathons, reach out to businesses — whatever it is, you can do it, and you can start right now.

Resources for getting started

Recommended reads

We asked Trevor about three books or blogs that have influenced him: