Back in the early 2010s, Venmo had a phenomenal data scientist, Delano McFarlane, who basically built Looker before tools like Looker existed. Venmo was also a big champion of startups like Looker and Mixpanel, signing up for their services as one of their earliest customers and providing product feedback.

Why Invest in Data from Day 1

1. Shared, visible data will motivate your team to be efficient and effective

At Venmo, we created a strong culture where everyone was data-obsessed. As a marketer, I didn’t know anything about SQL until Iqram, the co-founder, sat me down and taught me how to use SQL to pull data that I needed. Once I learned how to do this, I became fascinated with seeing the impact of my work in the numbers. This was super motivating!

When people can see their impact in a quantitative manner, they are very likely to be more motivated.

According to McKinsey, data-driven companies are 23 times more likely to acquire customers, 6 times more likely to retain them, and 19 times more likely to be profitable.

2. Setting up robust data infrastructure will allow you to scale without being hampered by technical debt

“We do manage all of our data! We have google spreadsheets and we track everything weekly!”

While this manual approach may work for the first year or two of your company’s existence, it will not cut it when you experience exponential growth and start onboarding hundreds or thousands of users per day.

Not only will you have less time to manage your data, but you’ll also have a higher volume of data and more data points that need to be interconnected in order for you to understand how the business is performing.

By investing early in a robust data pipeline, you can ensure that every new data source—whether it’s transaction data, customer information, or compliance data—is seamlessly integrated into your system. This will allow you to always focus on growth rather than scrambling to retrofit systems.

Case in Point: Stripe, one of the world’s leading fintech companies, prioritized building a flexible, scalable data infrastructure early on. As a result, they’ve been able to rapidly scale across markets, products, and regions without facing severe operational bottlenecks.

3. Detailed data will allow you to unlock customer insights and create delightfully personalized experiences

Even in our earliest days, every Venmo employee could tell you:

1. What types of users we had

2. What types of transactions people were making

3. Which cities our users were concentrated in

4. What emojis people were using in their payment notes

5. The average number of friends our users transacted with on a regular basis

This was before tools like Looker existed.

However, I feel that very few fintechs I meet with have this level of granular understanding of their users and I’m always surprised by it given the plethora of data tools that now exists compared to what we had available to us in 2013.

While data can be used to drive important business decisions, it can also be used to come up with creative customer-facing campaigns. For example, since we had data on who was using which emojis in their Venmo payment notes, we had a leaderboard that we sent via email to top users to show them who was leading in pizza emoji payments or vacation related emoji payments. It was a really fun way to increase engagement, and show our users that we appreciated all the creative ways they were using Venmo.

4. Compliance, of course

Last but certainly not least, strong data infrastructure isn’t just efficiency and creating delightful customer experiences — it’s about not getting your ass kicked by regulators.

Regulators increasingly require stringent data protection measures, and a strong data pipeline can help protect your company from compliance violations, reputational damage, and costly legal battles.

Some studies show that the cost of non-compliance is 2.71x higher than the cost of maintaining robust data.

Fun story

I spent over 3 months managing a project to help appease OFAC (Office of Foreign Assets Control). We had too many payment notes between users that looked like the following:

“Saki bombs! 🍶💣”

Unfortunately, that’s NOT how you spell SAKE (the Japanese drink) and Saki is apparently a small terrorist group. That word paired with the word “bomb” was never going to end well, so we had to find a way to avoid triggering OFAC alerts every time a bunch of college students went out to drink.

The solution? I wish I remembered who at Venmo came up with this brilliant idea, but we decided to create a new feature (emoji autocomplete), as a result of these OFAC issues.

Now, whenever you type in a popular phrase in Venmo, you’ll notice that it’ll suggest replacing your written note with a string of emojis instead.

For example, when you type in “rent,” you’ll see that we suggest the following emojis: 🏠💸

And that’s the story of how compliance led to a really fun new feature on Venmo. :)

Anyway, invest in data! From day 1! It’s never too late. Do it. Do it now.

Most of the time, it's the founder's fault.

Mistake #1: Not preparing a brief

As a founder, you have likely been thinking about your company and what makes you special for at least a year. The PR agency has just met you. They don't really know what you're all about. You're going to have to teach them. Even the best PR agency is not a mind reader.

Setting your PR agency up for success is your responsibility. How do you do this? Draft a brief. Your brief should include:

• Your Mission & Vision

• Your target demographic

• Why you're special

• Why PR? What about PR will help move the needle for your business?

• Which news outlets or influencers you think are a great fit for your target demographic

• What a successful PR engagement looks like to you

Mistake #2: Not having an internal owner

If a clear owner is not assigned, your PR agency will waste a lot of time and energy trying to track down the correct stakeholder.

Identify someone on the team who is responsible for:

• Updating the PR team on critical strategic shifts (hopefully not happening too often, but if you're a startup, this is going to happen at some point...)

• Helping to schedule calls with reporters (Your PR team likely doesn't have visibility into exec calendars. You need someone internal to help coordinate.)

• Running weekly syncs with your PR team

• Writing up recaps of work completed in the previous week and work-to-be-done in the upcoming week

• Documenting feedback and insights from reporters (as relayed by your PR team) about how the brand's narrative is landing

Mistake #3: Not making time to educate

Occasionally, your PR team may flag that a reporter is trying to learn more about a topic in which you may be a domain expert. Even if the reporter has no intention of quoting you or writing an article about you, make time to speak to these reporters.

Building trust with reporters who cover your industry is an important pillar of any successful PR program. If you think you're going to get a Forbes reporter to write a cover story about you without putting the work into building relationships with reporters, then you're going to be disappointed. Because guess what – if a reporter wants to write a cover piece about you without ever having met you, it likely means that:

1. You're past the point of needing PR to become a successful company or;

2. You're about to go to prison because you did something so egregious that everyone knows about it

Mistake #4: Not being able to tell the difference between a great PR agency and a terrible PR agency

A great PR agency will say: "We can't guarantee a specific number of press mentions or press pieces per month because it depends on how much work you're also willing to put into this partnership. It depends on how many deskside chats you're willing to do, how many phone calls you're able to take, etc."

A terrible PR agency will say: "We can guarantee at least 1 press piece per month!"

A great PR agency will help you build your brand's narrative and point out differentiators that they think will resonate with the press.

A terrible PR agency will take whatever copy you provide to them about your company, paraphrase it, and regurgitate it to a bunch of reporters.

A great PR agency will ask for a lot of communication with you. They might even feel like "a lot of work" and "high maintenance" at times.

A terrible PR agency will likely only contact you to let you know when they have secured a placement for you.

Need help standing up your PR function and creating a cohesive marketing & PR strategy? Hit me up. I've been doing this for the past 10+ years.

Call me old-fashioned, but I think there is so much value in true grassroots marketing. If anything, you're more likely to stand out in an age where thousands of ads are being shown to a single individual on a tiny screen all throughout the day.

However, I have met very few founders who have the drive and energy to even attempt on-the-ground, grassroots marketing. And I can't help but think that they're kinda lazy...

When I started out as a marketer at Venmo, I was mostly working with one other incredible marketer, Sylvia Pak, and one of the co-founders, Iqram. Iqram had a real passion for brand and marketing. He was a hustler, and I think this is partly why Venmo was so successful.

I can't help but laugh when people say things like, "Wow, Venmo was such an overnight success!"

"Overnight success" could not be further from the truth. Venmo was so much hard work for many years by an amazingly hard-working group of smart individuals who lived and breathed Venmo. I'm honestly shocked looking back on my younger self, because I have no idea why I was so obsessed with Venmo being a success. Maybe it's because I was young and single and really craving one big win in my tech career. I don't know.

God bless Mike Vaughan, our COO, who was my manager at the time. I slacked, texted, email him at all hours of the day every day for years and he never lost his patience with me. He knew how to unleash all my energy on project after project.

Back in the day when nobody in NYC had ever heard of Venmo, we were trying out all sorts of shenanigans to get people's attention. Here are a few wild things we tried that were non-scalable and non-lazy.

1. We printed out lottery-like scratch off cards and handed them out to people standing in line waiting to get into night clubs. (Shout out to Sylvia for this brilliant idea). Scratch off cards were worth anywhere from $5 to $500 and we handed them out to tons of people all over NYC waiting to get into clubs. They could redeem the amount with a unique code if they downloaded the Venmo app. Note: People waiting in line are very likely to pay attention to what you have to say because they can't go anywhere; they're stuck in a line.

2. We offered to give $5 to people waiting in line for buses all over NYC. (So, I'm not sure if anyone else on the team did this other than myself because at the time, I was constantly taking the QM express buses between my place in Manhattan and my parents place in Queens. Haha.) But, to my earlier point about people waiting in line being receptive to conversation...people waiting for the bus with me nearly always downloaded them app when I offered them $5 to try out Venmo.

3. We went bar-hopping and told people we would repay them for their drinks on Venmo. Things got aggressively competitive one night between me, Sylvia, and Iqram – we wanted to see who could get the highest number of downloads that night – and we ended up getting ourselves kicked out of a bar.

4. We gave out Venmo branded coasters to restaurants all over NYC. This was a fun one. We printed out coasters and asked restaurants and bars to provide them at tables because lucky patrons would be able to get repaid for part or all of their meal by downloading Venmo.

Lastly, shout out to Thomas Jeon (engineer) and Sylvia Pak for coming up with this one. We broke Venmo one day after launching a game called the Venmo money tree. We launched a website that showed a tree with leaves falling. You had 30 seconds (or maybe it was 1 minute, I can't remember) to click on as many leaves as possible. Each leaf was worth a certain amount of money, and you had 3 tries to collect as many leaves as possible. Once you had your total amount, you could cash out via Venmo. This ended up being way more successful than we had anticipated (driven by college students), and Venmo actually broke for a day because we had too many people using it.

In conclusion – do something different. Get creative. Get weird. Be the weirdo standing at bus stops asking people if they know about your product.

Mistake #1: Not defining what your website is meant to do

"We need a website."

"To do what?"

It's important to identify the main purpose of your website from the outset:

• My website is primarily meant to serve as an online extension of my brand (e.g. Zero Bond, Van Cleef)

• My website is primarily meant to drive customers to my BD team (e.g. Hubspot, Compound Planning, Addition Wealth)

• My website is primarily meant to drive online sales (e.g. Sephora, most retailers)

• My website is primarily meant to establish my brand as a thought leader in the space (e.g. Bridgwater, McKinsey)

• My website is primarily meant to provide information (e.g. Wikipedia, of course.)

• My website is primarily meant to share stories (e.g. Cereal, )

• etc.

DO: Identify your website's primary purpose before you hire a designer and marketer to redo the entire site.

Mistake #2: Not understanding when users are likely to visit your site (i.e. where in the user journey does the website appear?)

Consider this. By the time you go to jetblue.com, you already know:

• What Jetblue is

• What you're trying to do on their website

Going to Jetblue.com is probably the last step you take before you ultimately make a purchase from them.

Now, consider a new CPG brand from whom you made an online purchase in the last 3 months. When did you first visit their website? Was it after you saw an ad on Instagram? Was it after a friend recommended the brand to you? How many times did you visit the website before you ultimately made a purchase from them?

I'm a recent fan of the skincare brand Le Mieux, but it took me several visits to their website before I finally pulled the trigger and purchased a variety of products. i.e. I visited their website earlier in the user journey than I would have visited a site like Jetblue.com.

Now, consider the last time you hired a service provider – perhaps a lawyer to establish an LLC, or a home contractor to renovate your kitchen. Did you go to their website? If so, what were you looking for on their website? Were you looking to hire them at the click of a button? Probably not. You were probably looking for testimonials, qualifications, social proof, a sense of pricing, and contact information so that you could connect with the service provider and have a conversation.

You're likely viewing service provider websites in the earlier stage of the customer journey to help decide who's worth even reaching out to.

Understanding when in the user journey a person is likely to visit your website will help you determine what information and what amount of information is necessary on your site. If it's earlier in the user journey, you may need to do a bit more heavy lifting and educating about your product or services on your site. If it's later in the user journey, you may need less educational content and more focus on a seamless way for users to take action.

DO: Conduct some analysis on when users are likely to visit your website during the customer journey.

Mistake #3: Terrible information hierarchy

One of the first things I do with website clients is review their top navigation menu. The top navigation menu will dictate how information is organized throughout the entire website, so it's worth spending as much time as you need to get this exactly right.

Rule #1: Make sure information is MECE – mutually exclusive, collectively exhaustive

Rule #2: A maximum of four top nav menu items, plus one call-to-action button is best

Rule #3: Consider how your top nav menu will display and function in mobile view

DO: Spend time organizing all necessary website content into a clean and clear top nav menu.

Mistake #4: Information overload / Too much copy

People will most likely spend less than 1 minute on your website. It is not a good use of time or energy to pour your entire company's life story onto your website. Your website is meant to lead the user to the next step of the marketing journey.

According to MetricHQ, "A good benchmark for Average Time on Page is 52 seconds, across multiple industries. Based on data from 20 billion user sessions, B2B websites have the highest Average Time On Page of around 82 seconds."

Companies who dump too much information on their websites are not thinking about marketing as a series of touchpoints with the user. The website is just one touchpoint with the user; it's not the whole enchilada.

DO: Consider leveraging the minimum amount of information necessary on your website in order to lead a user to the next marketing touchpoint.

Mistake #5: Trying to cater to everyone

Pick your most compelling target audience and design your website for that persona. Stop trying to cater to everyone. You'll just end up with vague, generic copy that ultimately stands out to nobody.

Go all-in on your main audience. Succeed with them first and branch out after securing a foothold in your industry. You can't be inclusive as a business if you're broke and no longer exist.

DO: Recognize that being inclusive is great, but only helpful if you're still in business and can cater to everybody instead of nobody.

Mistake #6: Prioritizing aesthetics over functionality

I get it. Fancy animations and graphics can be cool, but don't implement cool design-y things on your site just because they look cool. Make sure your cool, fancy animations serve an actual purpose – whether it's furthering your brand's narrative, clarifying information, or assisting the user in taking a desired action.

Here's a fantastic example of a company that leverages cool design to emphasize its brand narrative and value prop.

If you go to the Compound website, you'll see a section where you can hover your mouse over two sentences.

When you hover over the first sentence, it comes into focus.

When you move your mouse to the second sentence, it comes into focus as the first sentence becomes blurred.

This is such a great example of design supporting functionality and messaging!

DO: Ensure that your design and animations enhance functionality and communication.

Mistake #7: Not leaving room for growth

Give your website a structure or architecture that can growth with your business. For example, maybe you only offer one product today, but if you plan on offering a suite of products in 6-12 months, you may want to ensure that you can easily add more products to your Product page. Or perhaps you plan on hiring a content marketer in 6 months and leaning into original content creation; make sure it's easy to add a blog or news section to your website.

DO: Think about what your business will most likely look like in 6-12 months and create an architecture that can easily accommodate growth.

My favorite websites lately

• Cereal Magazine : I love the simplicity and dummy-proof filtering.

• Bathhouse : An example of a business that knows why people are coming to their website - to book.

• Brimstone : Taking a giant rock of a problem and making it super digestible. An exercise in stripping down messaging to the most critical points only. Less is more.

• Anywhere We Roam : Excellent job of presenting tons of information in a beautiful, well-organized manner. Places and Cities could have been more MECE though.

• Drybar : They handle the complexity of their business model really well. Drybar needs to present users with the ability to book in-salon appointments, information about how to become a franchise owner, and sell products from their CPG brand. They handle all three pretty seamlessly on their website. Their website shows clear acknowledgment that the money-maker (and most effective way to leverage a website) is selling their CPG products.

• Cocoon Weaver : Great example of a website that's designed to simply drive traffic to app downloads.

• Aesop : Aesop does a wonderful job of presenting the brand in a consistent manner across all mediums - whether it's the interior design of their stores, their packaging, or their website.

• Compound : Demonstrates a strong understanding of how to balance animations and copy. Their design elements amplify rather than distract from messaging.

• Bending Spoons : Powerful storytelling.

• Pebble : Simple copy. Great use of videos to amplify value props.

The best brand briefs allow anyone on your team – product managers, engineers, ops managers, recruiters – to produce collateral that is brand-aligned. As a marketing leader, the most important thing is to put yourself in the shoes of a non-marketer when you're writing the brand brief. It's important to provide tangible, straight-forward examples that will realistically arise for various non-marketing members of the team.

What Is a Brand?

The Typical Brand Brief Structure

i.e. the stuff you'll find on Google

I'm going to basically copy/paste the structure that you'll see everywhere else in case you're too lazy to Google it yourself.

1. Vision & Mission - People define this differently, but I always define it as:

   1. Vision is what the world will look like when we are successful.

   2. Mission is how we move towards that vision. It's what we do each day to get ourselves closer to that future-state.

2. Who We Are - If a reporter asked you to describe your team in 1-2 sentences, how would you respond?

3. What We Offer - If a reporter asked you to describe your service or product in 1-2 sentences, how would you respond?

4. Our Values - How do we promise to operate as a team? What promises will we uphold for our customers?

5. Who We Serve (i.e. Target Audience) - Don't say everybody, because a product that's designed for everybody is really designed for nobody.

6. Our Competition

7. Why We Will Win - Why do we think people will choose us over the competition? This includes product positioning and competitive advantage.

8. Brand Principles - High-level guidance on how the brand should always come across. A good way to think about this is, "If you asked people to use 3 adjectives to describe your brand, what 3 adjectives would you want them to choose?"

9. Brand Voice & Tone - We'll get into this below.

Secret Components of a Bullet-Proof Brand Brief

This is where I'm sharing the extra good stuff!

Secret Component #1: Social Media Posts We Hate & Social Media Posts We Love

It's not enough for your brand brief to state that your brand needs to feel "polished" or "playful" or "rebellious." You need to provide tangible, visual examples of what is or is not polished, what is or is not playful, what is or is not rebellious.

A great way to do this is by including Social Media Posts We Hate and Social Media Posts We Love.

The "Social Media Posts We Hate" may come from brands you love and admire but represent the opposite of what you're trying to achieve with your own brand. For example, let's say you have a brand that is for high net worth individuals (HNWIs) and your brand principles are "understated" or "quietly luxurious."

You might share a few posts from Klarna, a fintech company that targets a younger demographic and show what it means to be bold and loud rather than understated or quietly luxurious.

(Don't get me wrong - I think Klarna has really great, distinct branding that works for its target audience; it's just not understated.)

You should compare and contrast examples and explain why certain images are or are not brand-aligned.

Secret Component #2: Provide Specific Situational Tone Guidelines

What's the difference between voice & tone?

Think of your best friend. You can probably recognize their voice regardless of whether they are happy, excited, mad, or sad. Their voice remains consistent. What changes, depending on the situation, is their tone.

Voice is constant. Tone is situational.

Your standard brand brief should include high-level guidelines on voice. For example, let's look at Tiffany & Co.

The Tiffany tone of voice voice is witty, elegant and classic.

Tiffany & Co. often pairs beautiful, elegant imagery with playful puns.

Pair your high-level voice principles with specific situational tone guidelines.

Let's say you have a mobile payments product called Payme. The voice may be "friendly, warm, and witty."

However, these are various situations for which you should provide specific tone guidelines. For example:

Situation #1: A mobile screen that describes what KYC means

Tone guideline: Lean towards straightforward and informational while being friendly and warm.

"<header> Let's get to know each other!

<body> We need to verify your identity before you can start using Payme. This helps us protect you and our community. And don't worry, we won't share your information with anyone else."

Situation #2: An email to a user that has violated our user agreement

Tone guideline: Stern and matter-of-fact without being rude.

"<header> Uh-oh, you've crossed the line.

<body> Dear {first name} - We are writing to let you know that you have violated our user agreement by ______. At this time, we do not allow users to ____. Your payments have been frozen until you reply to this email and confirm that you will immediately cease ____ activity. If you believe that an error has been made, you can reach out to {email address}."

Secret Component #3: Choose a Celebrity

This is a surprisingly simple tool that can help get your team aligned quickly.

Choose a celebrity whose voice & tone are very distinct and best match your brand. Ask your team to envision whether they can picture this celebrity saying the copy that is being written, posting the images that are being shared, etc.

It's much easier to write copy, read it aloud, and ask yourself, "Can I picture Dwayne Johnson saying that?"

I hope the above secret brand brief components can help you and your team take your brand brief to the next level!

They agree that it would be most efficient for them to split up and interview as many candidates as possible and return in a month with a recommended candidate.

They part ways and travel all over the world to interview various chefs. After a month, they reconvene.

Owner #1 says, "I have found the best chef to run our Chinese restaurant. She is a former recipient of the James Beard award from New York, and a master at combining traditional Chinese ingredients with classical French techniques."

Owner #2 says, "I have found the best chef to run our Chinese restaurant. I found him in Hunan where he runs the most popular restaurant in town. He can bring truly authentic Hunan cuisine to America."

Owner #3 says, "I thought we were opening a Chinese fast food spot, so I found someone with robust experience setting up and running a kitchen in Panda Express."

Obviously, these three owners had different visions for their Chinese restaurant. They could all be equally successful—a Chinese-French fusion restaurant sounds amazing, as does a traditional Hunan restaurant or a reliable Chinese-American takeout spot. But without alignment, it is impossible to move forward or to identify what success looks like.

That's why many design and brand agencies will refuse to work with you on revamping your brand, website, app design, etc. if you don't have a thoughtful, organized creative brief.

I find that most founders and entrepreneurs love working on their brands. However, so many of them waste time and money by failing to do the one thing that I consider to be the most important step in the process – writing and aligning all key stakeholders on a single creative brief.

Taking 2 extra weeks to develop a robust brief and align your team can potentially save you hundreds of thousands of dollars and months of frustrating conversations. Why wouldn't you take 2 weeks to correctly develop a brand that will last you 2 to 20 years??

If your answer is, "I just don't have time," it means you don't have time to redo your brand. Don't even bother getting started because you (and your creative partners) will not end up happy.

Case Study

I'll share a great example of my own failure to follow the above advice.

I had just joined a wealthtech company with two co-founders – one had a typical serial startup background and the other came from a traditional finance or Wall Street background. We'll call them Startup Steve and Wall Street Wilson.

Within my first month of starting the job, I requested that I run my typical process of gathering opinions and insights from key stakeholders across the firm, including both co-founders. Since we had an upcoming executive offsite, I asked if we could allocate 60 minutes to doing a brand workshop during which we could align on key concepts that would be included in the brand brief. The brand brief was to be shared with our creative agency who would deliver a new brand identity and website.

Despite pushing for some amount of time, in-person or via Zoom, to collect opinions from both founders, Startup Steve insisted that Wall Street Wilson would not have an opinion on brand direction, logos, or website design and that including him in ongoing brand-workshops would be a waste of time.

The best I could do was send out a short Google survey to try to get a superficial grasp of Wall Street Wilson's preferences.

I drafted the creative brief, which was heavily biased towards Startup Steve's preferences – quirky and different.

The designers spent about a month developing a few early concepts. After they delivered their early concepts, Startup Steve requested that the designers lean even further into the adjective "quirky."

However, this is where things began to take a bad turn. The co-founder, Wall Street Wilson, saw the early design concepts and suggested that the designers had a terrible understanding of our target audience and that we needed to look more like a traditional finance firm – trustworthy and established.

Not surprisingly, the designers pushed back and stated that Wall Street Wilson's request was completely contrary to what we had stated in our creative brief.

Needless to say, there was no scenario in which both founders would end up happy. After months of frustration, we finally found some middle ground. However, I was kicking myself for not following my typical process. Thankfully, the creative agency had worked with me several times before and knew that this was a bit of a fluke. I was still pretty mortified by the whole situation though.

This example just goes to show that even with a creative brief, success can be elusive unless you take appropriate steps and time to get stakeholder alignment on the brief itself.

So, how do I write a robust brand or website brief?

Stay tuned for my next few posts on:

1. How to write a kickass brand brief

2. How to write a foolproof website brief

I also have a video interview coming up with my absolute favorite creative agency, so be sure to Subscribe!

How tempting! 

RESIST!

You’re a startup and you’re cash-strapped. I get it. A good discount is always appealing. But one counterintuitive way to lose a lot of money is by signing up for those “annual discount” packages with B2B SaaS vendors and infrastructure providers.

It is painful how often I see startups burning through cash on monthly subscriptions and services that are no longer relevant 3 months after they signed up for those services.

Startups are constantly changing. The things you needed last week may not be the things you need next month. So why the hell would you lock yourself into long-term financial commitments?! Just don’t.

Your teams will also be in flux as you hire more people and new functional leaders. The marketing and operational infrastructure that you need long-term will largely be dictated by:

1. The people on your team and how they prefer to work together

2. Your ideal GTM motion, which will take time to figure out

3. Your ideal customer journey, which will also take time to figure out

And here’s the thing about contracts:

1. You generally cannot re-negotiate NOT paying the rest of your contract just because your company evolved or changed

2. You can always re-negotiate from a monthly contract to an annual contract and ask for a retroactive discount in exchange for converting into a long-term customer

Just think about the incentives for B2B SaaS companies and vendors. They have zero incentive to help you renege on a long-term contract, but they have every incentive to try to keep you as a long-term client. In other words, they will not work with you to renegotiate an existing long-term contract, but they will work with you to meet you in the middle and help you convert to a long-term customer.

As you’re reading this, I’m sure you’re thinking that this is all obvious. But I can’t tell you how many CEOs I meet with who have blown through tons of cash on long-term contracts that they no longer need and are desperately trying to get out of.

One question I get often is:

“Should we implement Salesforce or Hubspot, or something else?”

There are tons of blog posts about this, and I think Zapier does an excellent job of explaining the major differences between Salesforce and Hubspot here.

But here’s my high-level take:

• If your marketing and sales team are highly synchronized / intermingled, you will likely benefit from having both teams on Hubspot. This is because Hubspot has sales CRM features that are powerful enough to empower sales and BD teams, and it excels at providing marketing tools like landing page creation, email drip campaigns, etc. that connect to your sales CRM.

• If your sales team and marketing team are highly independent of each other and you want very detailed, robust reporting on the sales side, you may be better off using Salesforce as it’s more highly customizable to various sales funnels.

• If you’re a lean startup and your marketing and sales people are the same people, don’t waste your money on either! Get as far as you can with more affordable tools such as Pipedrive, Folk, Mailchimp, Mailshake, Loops, Airtable, etc. 

I strongly believe that things should feel like they are breaking before you upgrade to expensive, paid services and platforms. If you feel like, “Wow, we outgrew this system 3 months ago,” then that’s a positive thing. You’re ready for the grown-up systems. Until then, save your cash. You don’t know when the next financial crisis will hit and VCs tighten their purse strings, you don’t know when you’ll have to pay a massive amount to fix technical debt that is not allowing you to scale properly, etc.

Stick to the monthly subscriptions. Trust me, you’ll end up saving money, time, and stress. And your newly hired functional leads will thank you for not locking them into shitty systems that you signed up for with an inadequate amount of expertise to make a wise decision. 

Fast forward over a decade – I'm hired to run marketing for a fintech company. As soon as I am hired, the CEO pushes me to hire a growth marketer. I tell him that I would much prefer to hire a generalist because in my experience, you need generalists to help identify what types of marketing activities really move the needle in the early days. However, the CEO points to several other companies and competitors that he would like to emulate and shares that growth marketers were critical early members of those teams. He insists that I recruit a growth marketer as my first hire.

We do end up hiring a growth marketer, and she's fantastic. In fact, she's the best growth marketer I've worked with in my career thus far. She can target ideal customers like a ninja and optimize growth campaigns like nobody's business.

Unfortunately, this exceptionally talented human sat bored for many months. Why?

1. The company was not yet in a position to fully scale growth marketing campaigns; you generally want to have a strong content creation mechanism going so that content can be effectively leveraged by your growth marketer across various campaigns.

2. The company decided to pivot more towards a B2B model in which growth marketing became a lower priority than sales enablement and traditional PR.

Rather than trying to replicate the exact composition of your competitors, optimize for individuals who are passionate about the problem you are trying to solve.

Hire generalists who:

• Are driven to succeed and make a name for themselves

• Desperately want that IPO or acquisition as much as you do

• Have the confidence to flex into new roles without much experience or expertise

• Love to learn from those who do have more experience or expertise

• Are well organized and thoughtful

• Understand that success is the result of consistent hard work

Give those generalists a high-level vision and goals. Ask them to report back on what's working and what's not working. These insights should guide your hiring plan. These insights will tell you whether your next hire should be a growth marketer, content creator, or a BD professional.

Stop looking at how your competitor is hiring. You need to hire based on your own strengths, weaknesses, and opportunities. For all you know, your competitor's CEO could be killer at BD, and that's why she has hired zero BD professionals even though BD is what's moving the needle. And perhaps you are absolutely shit at BD and should be hiring an experienced BD rockstar even though your competitor has seemingly hired none.

In sum:

1. Evaluate your own strengths and weaknesses

2. Hire kickass generalists who complement and amplify your own skills

3. Garner insights from the generalists (LISTEN and OBSERVE)

4. Hire specialists based on your insights from the generalists

"But I never let my emotions sway my business decisions."

I find it a bit baffling that society, especially the business world, upholds completely emotionless decision-making as a virtue. After all, any strength taken to an extreme becomes a weakness.

Why is being extremely emotional viewed as a critical flaw while being extremely rational is upheld as a strength?

We don't need extremely rational business leaders. We need mindful business leaders.

Why Data Isn't Everything

The time Venmo almost didn't get invented

When Venmo was fundraising, a VC firm considering the opportunity apparently conducted a survey to ask people whether they wanted a social feed attached to their payments activity. The result? A resounding, unequivocal "no." People responded that the two concepts didn't mesh, that the idea was creepy, and that finances should be absolutely private.

Imagine if the co-founders of Venmo walked away dejected and gave up. Thankfully for me, they didn't. They moved forward with their quirky idea and did manage to get funding from investors who saw the value of doing something different.

At the time, there was zero data supporting the need or desire for a mobile, social P2P payments solution. If the founders had placed all importance on data, they never would have launched the app that became the impetus for the phrase "fintech."

The time I lost about $40,000

I invested about $100,000 with a CIO who prided himself on never being swayed by his emotions. He built his whole brand around the idea of being an emotionless investor who relied heavily on data, knowledge of history, and pattern recognition.

While he was extremely good at all of those things – analyzing data, recalling economic history, recognizing patterns – his inability to even recognize when he was experiencing an emotion ultimately meant that he had never created any checks and balances for himself as an investor.

Ultimately, my $100k investment with him ended up being my worst investment to date, with a loss of about 40%. Serves me right for believing an investor who stated he didn't have emotions. Like, don't we all know that Vulcans don't exist?! And even Vulcans recognize that they have emotions. C'mon, Esther. That one's on you.

People like me who are extremely emotional (and I say this with pride as someone who feels things intensely) generally learn how to recognize extreme emotions, and we learn how to moderate ourselves. We know when extreme emotions can be a strength (e.g., a fiery passion that compels me to produce the highest-quality work I possibly can) and when they can be a weakness (e.g., that time I b*tched out a product manager for showing up to a meeting unprepared and permanently soured my relationship with a critical partner).

We need leaders who have experienced the pros and cons of making overly rational decisions, as well as overly emotional decisions. Leaders who learn how to do the following will be at a huge advantage over purely data-driven leaders, especially now that data has become so easily accessible and understandable with AI:

1. Recognize and acknowledge their emotions

2. Recognize when data may not be everything

3. Build internal checks and balances

The time they forgot they were pitching to humans

As an angel investor, I've come across many pitch decks. I've also created many pitch decks for startups. However, I often notice a huge disconnect between the verbal and written pitches I receive.

Most entrepreneurs are able to convey a palpable passion for the problem they are solving when I meet them in person. But for some reason, that passion is absolutely nowhere to be found in their written pitch deck.

Instead, the written pitch deck is just pages filled with a mix of hypothetical and aspirational numbers. CAGR this, MAU that, hockey-stick growth...just like everyone else.

Numbers are great, but as a marketer and former consultant, I know that numbers can be leveraged to tell whatever narrative suits the business.

Conveying passion and excitement are just as important to investors, especially to angel and VC investors. Yes, investors want a return on their investment, but they also want to feel excited about the vision that they are fueling. If VCs were only about the numbers, they wouldn't be VC investors – they would be PE investors. Lol.

So What?

My takeaways are the following:

• As a leader, tap into your own emotions as well as the emotions around you.

• Hire people who can leverage both rational and emotional parts of their brains.

• Create checks and balances for when you find yourself veering into either extreme.

• Don't trust anyone who says they aren't swayed by emotions. It just means they're lacking in self-awareness.

Mistake #1: Hiring a CMO Too Early

After receiving early signals of product-market fit, startups sometimes think that a CMO can magically accelerate growth. However, the key to accelerating growth is having a strong understanding of what actually drives growth for your particular business. And you don't need an expensive or fancy CMO to do that.

Depending on your business, you may require a marketing leader who has deep experience in:

• Brand building

• Product marketing

• Editorial content

• Sales enablement

• Ads management

• PR

The problem is, you won't know which of these things will have a disproportionate impact on your growth until you try each of them to some extent. The best type of person to experiment across these different facets of marketing will likely be a mid-level marketing generalist who has the following qualities:

• Strong Generalist – Experience doing the actual work and executing on brand, product marketing, content creation, sales collateral, PR, etc.

• Ambition – hire someone who desperately wants to be running their own marketing team one day

• Courage – great marketers are not afraid to experiment, and they know how to stand up for their ideas. The best marketing campaigns are often the most polarizing (I'll save this topic for another post...)

• Collaboration – successful marketing is extremely dependent on partnerships with product teams, web developers, videographers, PR agencies, event managers, etc. You need someone who is extremely collaborative.

• Analytical & Hypothesis-driven – you'll need someone, especially in the early days, who can quickly identify bright spots and synthesize learnings

Alternatively, you can hire a fractional CMO at a more affordable cost who can later convert into a full-time leader once you both know that it's a good fit.

The downsides to hiring a CMO too early include:

• You'll waste money: Blowing through your budget on a high salary for someone who may or may not have the best background for what your business truly needs

• You may be over-indexing on strategy vs. execution: In your early days, you want to maximize execution. This doesn't mean you should hire someone who has zero strategic thinking skills. It just means you want to lean towards someone who will roll up their sleeves and get campaigns out the door vs. someone who will ask you to hire multiple agencies and contractors to get the actual work done.

• Wrong network: Depending on your CMO's background, you may not be able to properly leverage their professional network to hire the right type of talent under that person. For example, if you have a CMO whose network mostly consists of product marketers and ad managers, but you realize after 6 months that the marketing tactic that moves the needle most is educational content, you're going to wish that you had hired a CMO who has a deep network within the content creation community.

Mistake #2: Copycat Mindset

I once worked for a founder who constantly bombarded me, and other team members, with articles, videos, and emails about what other startups were doing to accelerate growth. This accomplished three things:

1. It distracted everyone on the team from the work they were doing

2. It stifled the team's ability to generate original ideas

3. It pissed everyone off and demotivated the team

Rather than focusing on what others are doing, focus on your own business, your own opportunities, and your own strengths as a team.

One of the greatest strengths of the Venmo co-founders was their ability to be steadfast in their own vision and execution strategy amidst a slew of competitors entering the P2P mobile payments space. At many different points in time, they could have panicked and said, "Oh no, look what Google is doing to promote payments over Gmail!" or "Oh no, look what Facebook is doing to promote payments on Messenger!" Instead, they reminded the team about what made Venmo special and why our users would choose us over much larger, much more well-capitalized competitors.

Mistake #3: Hiring PR without a Strong Marketing Counterpart

People complain about their PR agencies all the time. And yet, I have only had excellent results with my PR partners, and every company for whom I have managed PR can attribute a significant amount of increased brand awareness and success to PR. Why?

1. I always create an extremely detailed robust brief about the business, brand, and goals for any PR firm before I start an engagement. My PR partners know exactly what I am looking for and how I will evaluate their success.

2. I do recorded interview sessions between the PR agents who will be pitching and the company's co-founders so they know exactly what language to use when they describe us to reporters.

3. I do 1-2x per week check-ins with my PR partners to discuss the 3Ps:

   1. Progress (things that got done last week)

   2. Plans (things they're going to do this week)

   3. Problems (blockers)

4. I set up a dedicated Slack channel where PR agents can quickly secure quotes from executives of the company to relay to reporters who need insights in a pinch (this is an excellent way to build rapport with reporters)

You cannot just hire a PR agency and tell them you want to be in the WSJ next month. You'll blow through $10-30k monthly, and you won't see the desired results. PR is a partnership that requires active brand participation.

Mistake #4: Not Recognizing that SEO is a Long Game

Expect it to take years. End of story. Don't spend energy on this unless you're going to commit to generating valuable content, securing backlinks to your own site from sites with higher domain authority scores, etc.

Mistake #5: Starting Your Own Community

Community-building is its own marketing mechanism and often its own business model. Yes, it takes 30 seconds to start a new Slack workspace, Whatsapp group, or Facebook group. But it takes 2-3 years (of hard work and dedicated resources) to build a valuable, robust community that can drive revenue.

Unless you have solid proof that your business' key growth accelerator is community-building, I recommend leaning into leveraging and partnering with existing communities.