Cowboy Ventures’ Ted Wang: CEO coaching is ‘about having a second set of eyes’

Earlier this month, Cowboy Ventures’ Ted Wang joined us at TechCrunch Early Stage: Marketing and Fundraising, where he spoke about executive coaching and why he encourages founders in his portfolio to have a CEO coach. Wang, who has an executive coach himself, sees coaching as a key way to drive sustained personal growth, a factor that he believes separates the middling CEOs from the best ones.

Why CEOs need coaching

Just like professional athletes at the top of their game still need coaching, executives can need external validation and comment on where they are and aren’t delivering, Wang says. These insights can be tough for executives to catch on their own and might require a level of honesty that can be challenging for a CEO to expect from anyone involved with their company.

Roger Federer — the famous tennis player who has won 20 Grand Slam events — he has a coach, but he doesn’t just have a coach, he has a coach for tennis. I’m pretty sure Roger knows the rules of the game and all the different strokes he needs to hit, so why would he have a coach? The answer is really that it’s about having a second set of eyes; when you’re in the moment … it’s hard to be able to see yourself and assess yourself. (Timestamp: 4:52)

Coaches can help entrepreneurs reflect and reframe the things being communicated with them.

A good example — you might be at a board meeting and one of your board members is being critical of your VP of marketing, and one way to think of that is “Oh, OK, here are some things we need to solve for this person,” but another point of view that a coach might open your eyes to, is actually maybe this person thinks you’re not hiring the right people. (Timestamp: 8:59)

While advisers can help startups navigate tactical situations, therapists may be more focused on helping clients navigate emotional states and improve themselves. Coaching exists in a very nebulous gray area between startup advisers and licensed therapists, Wang says, but coaching is more focused on improving yourself as a business leader rather than solving a particularly vexing startup issue.

When you’re in the moment … it’s hard to be able to see yourself and assess yourself.

Greylock’s Mike Duboe explains how to define growth and build your team

With more venture funding flowing into the startup ecosystem than ever before, there’s never been a better time to be a growth expert.

At TechCrunch Early Stage: Marketing and Fundraising earlier this month, Greylock Partners’ Mike Duboe dug into a number of lessons and pieces of wisdom he’s picked up leading growth at a number of high-growth startups, including StitchFix. His advice spanned hiring, structure and analysis, with plenty of recommendations for where growth teams should be focusing their attention and resources.

How to define growth

Before Duboe’s presentation kicked off, he spent some time zeroing in on a definition of growth, which he cautioned can mean many different things at many different companies. Being so context-dependent means that “being good at growth” is more dependent on honing capabilities rather than following a list of best practices.

Growth is something that’s blatantly obvious and poorly defined in the startup world, so I do think it’s important to give a preamble to all of this stuff. First and foremost, growth is very context dependent; some teams treat it as a product function, others marketing, some sales or “other.” Some companies will do growth with a dedicated growth team; others have abandoned the team but still do it equally well. Some companies will goal growth teams purely on acquisition, others will deploy them against retention or other metrics. So, taking a step back from that, I define growth as a function that accelerates a company’s pace of learning.

Growth is everyone’s job; if a bunch of people in the company are working on one problem, and it’s just someone off in the corner working on growth, you probably failed at setting up the org correctly.  (Timestamp: 1:11)

While growth is good, growing something that is unsustainable is an intense waste of time and money. Head of growth is often an early role that founders aim to fill, but Duboe cautioned early-stage entrepreneurs from focusing too heavily on growth before nailing the fundamentals.

I’ve seen many companies make the mistake of working on growth prior to nailing product-market fit. I think this mistake becomes even more common in an environment where there’s rampant VC funding, so while some of the discipline here is useful early on, I’d really encourage founders to be laser-focused on finding that fit before iterating on growth. (Timestamp: 2:29)

Where to focus growth energy

The bulk of Duboe’s presentation focused on laying out 10 of the “most poignant and generalizable” lessons in growth that he’s learned over the years, with lessons on focus, optimization and reflection.

Lesson 1: Distill your growth model (“business equation”)

Growth modeling and metric design — I view as the most fundamental part of growth. This does not require a growth team so any good head of growth should require some basic growth model to prioritize what to work on. (Timestamp: 3:09)

The first point Duboe touched on was one on how to visualize your growth opportunities using models, using an example from his past role leading growth at Tilt, where his team used user state models to determine where to direct resources and look for growth opportunities.

Lesson 2: Retention before acquisition

The second lesson is to prioritize retention before driving acquisition, a very obvious or intuitive lesson, but it’s also easy to forget given it’s typically less straightforward to figure out how to retain users versus acquiring new ones. (Timestamp: 4:19)

Retention is typically cheaper than acquiring wholly new users, Duboe noted, also highlighting how a startup focusing on retention can help them understand more about who their power users are and who exactly they should be building for.

Lesson 3: Embrace ideas from all corners, but triage

Bringing on new ideas is obviously a positive, but often ideas need guidelines to be helpful, and setting the right templates early on can help team members filter down their ideas while ensuring they meet the need of the organization.

Silicon Valley comms expert Caryn Marooney shares how to nail the narrative

Caryn Marooney, Silicon Valley communications professional turned venture capitalist, spoke extensively on storytelling at TechCrunch Early Stage: Marketing and Fundraising. During her talk, she broke down messaging into four critical parts.

Marooney knows what she’s talking about: Throughout her time in Silicon Valley, she helped companies like Salesforce, Amazon, Facebook and more launch products and maintain messaging. In 2019, she left Facebook, where she was VP of technology communication, and joined Coatue Management as a general partner.

The presentation is summarized below and lightly edited for readability. Marooney breaks down her method into the acronym of RIBS: Relevance, Inevitability, Believability and keeping it Simple. A video of her presentation is also embedded below and contains 20 minutes of Q&A where she answers audience questions and covers a lot of ground.

Marooney has written extensively on this subject for TechCrunch, including this article, where she describes her RIBS method in detail. Last month, she expanded on this topic with her go-to-market strategy around building a hamburger.

‘The gift of editing is critical. Do not just write all your ideas and get very excited about what you think and ship it.’

Relevant

Why should anyone care? Does anyone care? That’s the point Marooney is making here. The message must be relevant to the audience before anything else.

The very first thing is why anyone should care. And it’s important to remember that as a startup, you’re in a situation where nobody knows you. And nobody thinks, “Oh, I should really care about this. So you need to be very specific about who your audiences are and why they should care and why it matters to them. Early on, too. Relevance is usually to a very small audience, and you earn the right every day to expand that audience.

So, for example, when I was first working with Salesforce, it was a very narrow set of salespeople, for small- and medium-sized businesses, there was always the sense that it was going to be a cloud provider for companies of every size, but you have to start somewhere. And when you’re starting somewhere, you can paint the bigger picture. But you have to be specific about the benefits to your smaller audience. (Timestamp: 1:48)

Inevitable

In addition to talking about Tesla, Marooney uses the counter-example of the Segway, which shows a great idea alone is not enough. Even though Segways were introduced as a world-changing mode of transportation, in 2021, Segways are mainly only used by mall cops and tourists.

How to pivot your startup, save cash and maintain trust with investors and customers

A few years ago, founder Sean Lane thought he’d achieved product-market fit.

Speaking to attendees at TechCrunch’s Early Stage virtual event, Lane said Queue, a secure digital check-in tablet for hospital waiting rooms that reduced wait times by uniting and correcting electronic medical records, was “selling like hotcakes.” But once Lane realized it would only ever address one piece of a much bigger market opportunity, he sold off the product, laid off two-thirds of the people affiliated with it and redirected the employees who were left.

Lane explained that what he really wanted to build is what his company — since renamed Olive — has now become, a robotic process automation (RPA) company that takes on hospital workers’ most tedious tasks so nurses and physicians can spend more time with patients.

Customers seem to like it. According to Lane, more than 600 hospitals use the service to assist employees with tasks like prior authorizations and patient verifications.

Investors clearly approve of what Olive is selling, too: Last year, the company raised three rounds of funding totaling roughly $380 million and valuing the company at $1.5 billion. According to Crunchbase, it’s raised a total of $456 million altogether.

In fact, VCs think so much of Lane that in February, they invested $50 million in another company that Lane runs simultaneously called Circulo, a startup that describes itself as building the “Medicaid insurance company of the future.”

Still, the path from point A to B was painful, and it might not have happened if Lane didn’t have a few things going for him, including a deeply personal reason to build something that could have greater impact on the U.S. healthcare system.

Alexa von Tobel outlines how founders should manage personal finances

Few people are more knowledgable on the topic of how founders should manage their finances than Alexa von Tobel. She is a certified financial planner, started her own company in the midst of the recession (which happened to be a wildly successful personal finance startup that sold for hundreds of millions of dollars) and is now a VC who invests and advises founders.

At Early Stage 2021, she gave a presentation on how founders should think about managing their own wealth. Startup founders can often put all their money into their venture and end up paying more attention to the finances of their company than their own bank account.

Von Tobel outlined the various steps you can take to stay out of debt, build credit and accumulate wealth through investments to ensure you have financial peace of mind as you take on the most stressful venture of your life: Starting a company.


Know your numbers

The first step in getting organized and being proactive is often taking inventory. Von Tobel believes that knowing your numbers and getting organized digitally is the first step to having financial peace of mind.

Know all your numbers. Know your net worth. What are your assets? What’s your debt? What does your total financial picture look like? Get everything online. You should have all the mobile apps downloaded so that, in minutes, you can actually see your full financial life. And keep it simple. Fewer accounts are better. I always tell people, if you have seven credit cards, plus three savings accounts, that’s a lot. You’re never going to be as good at managing your finances. Simplify your accounts. (Time stamp — 2:50)


Manage your credit and debt

Founder and investor Melissa Bradley outlines how to nail your virtual pitch meeting

Melissa Bradley wears many hats. She’s the co-founder of a startup called Ureeka, an investor at 1863 Ventures, and a professor at Georgetown’s business school. So it’s not an understatement to say that she understands the fundraising process from every angle. And moreover, she has both invested and fundraised for her own startup during this last year, where the landscape has shifted drastically. At TechCrunch Early Stage, she led a session on how to nail your virtual pitch meeting.

Bradley covered how to allocate your time during the meeting, how to prepare, how to close out the meetings with a clear list of action items, and what to avoid.

You can watch the session or check out the full transcript below, but I’ve also pulled out a few highlights from the talk just for you.

Enjoy!

Conversation > Pitching

One of the greatest shifts in the pitch landscape during the pandemic was the nature of meetings themselves. Because investors and founders can take 30 meetings a day from the comfort of their home, it means that conversation has been prioritized over presentation. Adding to the need for conversation is the fact that investors aren’t ‘getting to know you’ IRL as they would in the past, and so how you interact (not just the content of your pitch) is critically important.

Bradley explained that planning for extra time to answer questions and go deep on strategy is more important now than ever.

Now is the time to really have a conversation and deeply engage the investor in your story and your vision. You want to be conversational in nature, but still formal in tone. So you want to be respectful; you want to avoid jargon; you want to make sure it’s clear what you’re talking about. But it’s really much more of a two-way conversation than we’ve probably seen before. I think again, pace yourself, be really clear in advance how much time you have. One-third of the time should be spent on your pitch, and the other two-thirds, you should be prepared to field questions and really have that conversation. Pace yourself. Don’t rush through. If you only have 30 minutes, it’s probably not the best time to do a demo. You might want to follow up with a recorded demo or make an offer to do a demo afterwards. (Timestamp – 6:03)

Strategy > Projections

Building the right team for a billion-dollar startup

From building out Facebook’s first office in Austin to putting together most of Quora’s team, Bain Capital Ventures managing director Sarah Smith has done a bit of everything when it comes to hiring. At TechCrunch Early Stage, she spoke about how to ensure the critical early hires are the right ones to grow a business. As an investor at Bain Capital Ventures, Smith has a broad view into the problems that companies face as they search for the right candidate to spur organizational success.

In our conversation, Smith touched on a number of issues such as who to hire and when, when to fire, and how to ensure diversity from the earliest days.


What to consider when you first think about hiring

When a company is making its first hires — and then evolving into a bigger organization — the processes and needs may change, but the culture should be consistent from the beginning, according to Smith. From there, an emphasis on good early managers is critical.

I would really encourage you to take some time to think about what kind of company you want to make first before you go out and start interviewing people. So that really is going to be about understanding and defining your culture. And then the second thing I’d be thinking about when you’re scaling from, you know, five people up to, you know, 50 and beyond is that managers really are the key to your success as a company. It’s hard to overstate how important managers, great managers, are to the success of your company.

So we’ll talk a little bit about how to think about that, as there’s a lot of questions around helping people grow into management for the first time. You, as a founder, might be managing people for the first time, so how to think about setting up the company for success.

(Timestamp: 4:15)


How do you build culture in the new remote environment?

So you want to raise a Series A

During a seed funding round, a founder needs to convince a venture capital investor on a vision. But during a Series A fundraise, napkin-stage ideas don’t make the cut — a founder needs product progress, numbers, and revenue (or at least a plan to eventually generate some).

In many ways, the stakes are higher for a Series A — and Bucky Moore, a partner at Kleiner Perkins, joined TechCrunch Early Stage last week to give founders tactical advice on the process of raising one.

Moore spoke about storytelling over semantics, pricing, and where his firm sees itself “raising the bar” for startups.

Here are a few key points; a full video and a transcript of the entire conversation are linked at the bottom.


Explain to investors why you are raising now

More companies will raise seed rounds than Series A rounds, simply due to the fact that many startups fail, and venture only makes sense for a small fraction of businesses out there. Every check is a new cycle of convincing and proving that you, as a startup, will have venture-scale returns. Moore explained that startups looking to move to their next round need to explain to investors why now is their moment.

The way I think about “why now” is [that] it is an opportunity for you as a founder to convey a unique insight and understanding of your market opportunity, the history of the space that you’re in, why companies have succeeded or failed in that space, historically speaking, and what are the known challenges from a go-to-market perspective; what headwinds will you be up against at a macro level. These are all things that I think people like me get really excited about when hearing unique insight from founders, because it suggests that they’ve really studied their market opportunity, and they understand it. (Timestamp: 2:19)

Bootstrapping, managing product-led growth and knowing when to fundraise

Product-led growth is all the rage in the Valley these days, and we had two leading thinkers discuss how to incorporate it into a startup at TechCrunch Early Stage 2021. Tope Awotona is the CEO and founder of Calendly, which bootstrapped for much of its existence before raising $350 million at a $3 billion valuation from OpenView and Iconiq. And on the other side of that table and this interview sat Blake Bartlett, a partner at OpenView who has been leading enterprise deals based around the principles of efficient growth.

In this interview, the two talk about bootstrapping and product-led growth, expanding internationally, when to bootstrap and when to fundraise, and how VCs approach a profitable company (carefully, and with a big stick). Oh, and how to spend $350 million.

Quotes have been edited and condensed for quality.


Bootstrapping is directly tied to product-led growth

Product-led growth is all about efficiency — spending all of a startup’s capital and time on perfecting its product to capture new users and help the most fervent customers advocate for the product with others or perhaps the managers approving their expenses. That’s directly related to bootstrapping, since by evading VC investment, a startup has to be much more tied to customers in the first place

Tope Awotona:

With no marketing at all, Calendly begin to take off. So the initial users were in higher education, and very quickly we moved to the commercial sector. And all of that was because of the virality of the product. Seeing that, we just began to invest more into virality. So the combination of self serve, which is incredibly capital efficient, because you don’t need all of these sales people, and also the virality, instead of spending a bunch of dollars on advertising, you can really rely on the virality of the product and rely on the network of the users to really propagate and to enable distribution, just those are the two things that really allowed us to be successful. (Timestamp: 7:49)

We later discussed how the extreme focus on users can drive efficiency through product-led growth.

Blake Bartlett:

It’s the product and the distribution model, and they need to be tightly aligned. Tope spoke to some of this but I think first and foremost, even outside of metrics, it’s just how is the business built? And on the product front, the product is built, the jobs to be done so to speak, are oriented towards the actual user of the product, not their boss. SaaS historically was built for the boss because the boss owns the the budget for that department. So if you’re building a sales tool, build for the VP of Sales, and then hopefully the AEs will, you know, go along with it. But now with product-led growth, you’re actually building for that user. … Eventually, you can build the things on top that the boss cares about like the admin panel, and the KPIs and all that kind of stuff. (Timestamp: 29:35)


Product-led growth and international expansion

Four strategies for getting attention from investors

Being a successful early-stage investor is about a lot more than simply identifying trends. A successful VC needs to think several steps ahead. For MaC Venture Capital founder Marlon Nichols, it’s an ability that’s helped him spot big names like Gimlet Media, MongoDB, Thrive Market, PlayVS, Fair, LISNR, Mayvenn, Blavity and Wonderschool early on.

Nichols joined us on TechCrunch Early Stage to discuss his strategies for early-stage investing, and how those lessons can translate into a successful launch for budding entrepreneurs. Success involves not only a solid team and great ideas, it also requires the willingness and ability to change and adapt to an ever-changing world.


Getting ahead of the trends

Anyone can identify trends once they’ve broken, but a successful investor needs to see several steps ahead of the pack. This ability helps VCs know where to focus their attention and, eventually, how to weed out the snake oil from the true value pitches.

For us, that means taking a look at emerging behavioral trends and shifts in culture. What we’re looking to understand is where people and companies are going to spend their time and money – not only today, but in the future. So we do research to see if there are supporting factors for this thing sticking around and being successful. If that answer is yes, then we can dig a bit deeper. (Timestamp: 4:33)


Diverse from day one