Zero To A Hundred – Episode 6: Cracking The Subscription Code For Predictable Revenue With Garrett Wright!

Hey Accelerators! 🚀 In this episode, we’re diving deep with Garrett Wright into the world of subscription models. If you’re looking to turn your business into a revenue-generating machine with predictable outcomes, this is the episode for you. 💡 

🔹 What’s on the Menu:

• The secrets behind successful subscription models. 💼
• Understanding and optimizing unit economics for growth. 📈
• How to balance short-term profitability with long-term sustainability. 🔄

🔥 Why Tune In?

• Garrett shares his expertise on what it takes to scale a subscription-based business, focusing on customer retention, acquisition costs, and the importance of predictability. 
• Learn how to create a business model that investors love and customers stick with.

💬 Gem from Garrett: “Predictability isn’t just about stability—it’s the key to unlocking growth and securing investment.”

📞Get in Touch with Garrett:

🌐 Find Garrett on LinkedIn: / garrett-wright-661b263

About Stash: 

Stash is a financial platform and subscription business focused on empowering people to invest and achieve their financial goals. The company counts more than 4M accounts and over $3.5B set aside by hard working Americans, who save around $30 at a time on average. In the past year, Stash introduced StashWorks, a new financial wellness benefit that allows employers from a wide range of industries to offer savings and investing tools to their employees that go beyond standard retirement benefits.

Don’t miss out—hit that subscribe button and let’s accelerate your business from zero to a hundred! 💥

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Cracking The Subscription Code For Predictable Revenue With Garrett Wright!

I would like to welcome Garrett Wright. He is a fintech superstar. He has been with a good that has taken a company public. He is now the Chief of Staff for Stash, an investment app for the 99%. He’s been with them from $1 million in annual revenue, where they’ve taken to $100 million in annual revenue and raised over $400,000 million in investment capital. We’re going to cover some incredible topics that are going to help your business, such as subscription models, raising capital from investors, predictable cashflows, and financial forecasting for businesses of all shapes and sizes. Let’s accelerate together.

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Garrett, it is great to have you. Thank you for joining us.

Thank you. I’m super excited to be here. Awesome.

The Art Of Raising Capital

I want to dive in with you and talk business. You have been working with your company for a few years. You’re quite successful and can shed some interesting light on the entrepreneurs that tune into our program looking at growth strategies for their businesses. One thing I’d like to focus on because this isn’t for every business. It’s for many of the merchants and the entrepreneurs we talked to those who are looking to raise capital. Can you talk to me in general about the art of raising capital and how to approach investors to get them to invest in your blackboard?

Before I entered this space, particularly venture-backed early-stage startups, it was a huge mystery. I thought it was extremely numbers-driven. That may be my background in engineering, but the reality is that it’s almost all about FOMO. How do you create that fear of missing out? It’s so cute. It’s a sales process. You want people to get excited and people want to believe in something. They want to feel like they can’t miss out. You have to create that tension and this changes as the companies develop and mature. It’s particularly true in early-stage companies because there’s not a lot of data at the end of it.

You don’t have a lot of history. The financials are going to look upside down because you’re investing in the business. You need to create this story and that can happen in a variety of ways. It’s an early-stage company. You could be focused on downloads, usage metrics, and exciting charts that go up into the right. You’re in a hot market. AI is hot. FinTech was hot a while back. 3D printing, which was hot years ago and being in those markets makes it a bit easier.

The team can be huge. If you have a successful track record, people are going to believe in you and don’t want to miss out on the next thing that you’re doing. You can do this depending on the business, space, and background. There’s a variety of ways to do it. It’s critical to be thinking about this as a sales process, driving emotion, and driving people to a decision intention and creating that FOMO so people want to be engaged and make decisions and invest.

The other thing that I’ll say about it is it does shift over time. As you get more mature in your business, people start to focus on different things. It is harder to create FOMO with just the team or downloads. You have to start to show true unit economics and proven revenue growth. As you get further down the line, say you’re a public company. It’s almost exclusively about the bottom line and predictability. It does change as businesses mature and evolve. For entrepreneurs, it’s important to know where you are and that stage and have a strategy to how you’re going to create FOMO with potential investors.

I want to make sure that I’m clear on this. What I’m hearing from you is one of the main things you must do as an entrepreneur or business owner if you’re going out to raise capital. Especially if it’s your first round of raising capital. It’s building a story and building a story around that idea of FOMO. What you’re selling is what the market share could potentially look at and the traction that you have in your business. Whether it clicks or the amount of people who are visiting your site and you are selling your team. Those are some of the key aspects that are going to help you close that initial capital coming into your business.

Investors are making bets, and a lot of it is on people, on the traction, and in the space that you’re in.

Managing Investor Expectations

There’s something that you said about predictability and the bottom line. We’re going to come back to that. I just wanted to highlight that because the idea of predictability is important in your business. Before we do that, I want to stay on the investor track because it’s an important trap. Investors help you expand your business. You could be a hair salon and decide to franchise, bring in investors, and grow to 200 locations. By the way, things like this happen every day.

You could be the tech play where you need to build your engineering team and you want to expand your business and your offering to tens of thousands of clients in your servicing. Once you get that money through the door, how are you most effectively managing your investor’s expectations throughout their lifetime of investing in your platform?

It’s a great follow-up question because it’s going to put some guardrails around the FOMO. You don’t want to make stuff up. At the end of the day, you need to deliver once the investor makes that investment. You don’t need to hit the numbers. Investors know that not everything is going to work out. They expect it. They discount your plans but want to see results and things moving in the right direction. You need to deliver on what you said.

Building a long-term relationship or any relationship, whether it’s with an investor, partner, or a friend, is built on trust. Does this person do what they say they’re going to do? That’s critical as you’re thinking about building a long-term relationship with your investors. It’s clearly communicates what the plans are, what the risks are and shows results. You don’t have to nail your plan, but if you can continue to communicate through the tough spots, you can quickly learn, iterate, and solve problems. Bring the investors into those discussions in a way that makes them feel a part of the process but not guide the process. It can create a long-term relationship.

That will help you grow the business, bring in more expertise and the next round of capital. It’s not easy to strike the balance there but the founders I worked with have been great at this. It takes a lot of effort and a lot of thought on how you’re communicating, when you’re communicating and balancing the story with what you think you can deliver.

I like what you said about putting the guard rails around the FOMO you create when your investors are investing in your business. Number one, because your investors aren’t necessarily expecting for you to meet the Matrix or the metrics that you are pitching. A lot of times, they’re going to offer discounts, especially when you’re in a high-trajectory business. It is how you’re mitigating and managing risk and how you are communicating with those investors. Also, the results that you are delivering. At least, you need to get close to or work on reaching the targets that you’ve put out there from day one.

Those are key points. I will say that in my career, from a capital raising standpoint, raising real estate years ago. Earlier on, I did not always manage expectations as well as I should have managed expectations where it was the communication. Not necessarily delivery, but go going to my investors and saying, “I need help with something. We’re having an issue with getting the financing that we wanted at the rates we were trying to get them.”

The reason you’re open and honest with those type of things is not to create a sense of fear. If they’re invested in you, they’re investing in you in the long-term. They want to make sure the deal is going to get done. Otherwise, their money is at risk. A lot of times, they can make phone calls or create solutions for them that you as the novice business owner, are able to create yourself. It is key to have that open channel of communication with your investors.

It’s easy. I’ve definitely done this many times in the past. It feels a bit adversarial because they invested their money and maybe something went sideways and didn’t go exactly as planned. You feel responsible and you want to fix it. You have to remember, as you said, their interests are aligned. They’re on your side and want you to be successful so that they can make the money back. The trick is how you communicate those things. How do you make sure that you don’t create so much noise if you’re in the minutia of details? Make sure investors can track the storyline.

They’re not in the day-to-day. You have to work on how to step back and communicate clearly. “Here’s where we are.” “Here’s what we need.” “Here’s what the results are going to be.” “Here’s my specific ask.” They have lots of investments. They don’t have a lot of time but they will make time. It will help you if you’re specific and communicate clearly and try to keep the confusion to a minimum. It’s easy when you’re in the weeds of like, “We didn’t get this bill or this specific feature is three months delayed because of X, Y, and Z.” They don’t care. Think about the outcome that you’re trying to drive and what your ask is from.

Success Strategies

You get the investors in. You turn in, burning, and making things happen. You’re starting to show some results. Once you get past the iterative or idea phase, you’re in the business. What are some of the success strategies that you can create to build a unique business model? Especially with what you do in your business model.

Where I work is very much a subscription business. A subscription model is a great investors. I love them. They’re high margin and predictable revenue. Everybody likes predictability. They don’t want to be surprised. A lot of businesses moved down to this path of subscription. The key for a subscription business is understanding your unit economics because they can get out of whack. These subscription businesses can have high acquisition costs or low retention. That creates scenario where it’s cash-intensive to build the business. I think about it as a leaky bucket or a very good customer acquisition analogy.

 More like the leaky bucket of customers because you don’t want to leaky bucket of customers.

It’s expensive to refill the bucket and getting the cash is also very expensive from a dilution perspective. You want to understand the unit economics. How much does it cost to acquire a customer? Why? What’s your funnel drop-off points? What are customers trying to tell you with where they’re dropping off in that funnel or in your sales process? What part of the pitch is working or is it working? How do you double down on that? What’s your retention over time?

This can also be hard in the beginning because you don’t know. You’ve only been around for a few months. You don’t know what you’re 12 months or 24 months retention. You can use proxies and in my experience, the first few months are very predictive of what the rest is going to be. Looking at your cohorts and understanding what’s going on with them, why do customers stick around? Why did they leave? What makes them refer you to their friends? Getting a deep understanding of those key pieces of the unit economic puzzle. Including how much money you make from each customer is critical and how long it takes to pay back that investment.

Investors are going to be looking at these things. The sustainability of the business is wrapped up in that payback period, the unit economics. If you’re going to have a high-scaling successful subscription business, investors are going to be clamoring after. You want your payback to be sub-twelve months. It doesn’t have to be the right thing in the beginning, but that’s what you should be targeting. How do you do that?

That creates good cashflow and turnover so you can continue investing in customer acquisition and retention. As we’ve been working through the ups and downs of running the subscription business, one of the key takeaways is to stay focused on retention. I say that because you learn a lot from your customers. If you have good retention, you don’t have a leaky bucket, it creates all sorts of opportunities to build low-cost referral, organic acquisition, and loops to drive down your acquisition costs.

It also allows you to grow and expand with your existing customers versus having to keep acquiring customers. It becomes too cash-intensive. If you lose sight of that, it can build every month. You’ve invested a lot to acquire these customers and more than you think are gone in a month, 2 months, or 3.  You’ve got to reinvest more capital.

Understanding retention and what’s striving good retentive customer versus not is important. The last important piece is understanding the financial aspects, such as whether you have the right price. What are the margins? Are you competitive there? You want to create enough contribution from the subscription to support and sustain growth in the other pieces of the puzzles that you have to invest in whether that’s your office space and your product development.

Thank you so much for going over what the subscription model should look and the important aspects of building a successful subscription model. How you guys have done it is by focusing on unit economics. That customer acquisition calls to that cat. Look at what your funnel drop-off is for the success of your funnel. The efficiency of your pitch, the retention of the customer once you get them onto the platform, what your referrals look like and then ultimately what your profits are based on all of those ask.

Predictability

Those are the key measurements for measuring a successful subscription model and marketing plan. You visited that idea of predictability again, and that’s something that I want to discuss in depth. How do you create that predictability? In my mind, that is what ultimately will create a very successful business model for you.

It’s not easy. This is a lot of hard work day in and day out to get subscription models humming. I don’t think they’re ever done because the markets moving, new competitors are coming out and new features are required to keep your customers. It is hard work to build these models. Once you get them going, they’re powerful because they can buy time to continue to invest and work in other things because of their predictability of them.

What I think about how to forecast these businesses, how to think through scenarios is important. Sorry to harp on you on unit economics, but if you’re out raising money, this is what investors will ask you about. You understand those and know them well. If you don’t have information, try your best to lean on your investor for proxies and what they see in other companies that will help you predict some of these things.

That’s where I start every forecast in every model. What are the key drivers of this business? Whether it’s a subscription business or something else, because you need to know like how is the revenue generated. What’s the contribution after the variable costs? How much money do I need to invest to grow the business and understanding that and doing different scenarios to drive different sensitivities can help.

When I’m doing models, it’s where I always start. Top line and what’s the driver to the top line? What other investments do you need to make to develop that next feature, add that next add-on that’s going to increase your average revenue. What you’re trying to do, at least, I’m trying to do typically when I’m doing these forecasts is I start there. I started the P&L and I always land in cash. Cash is okay. You need to know how much you have, how much this growth plan is going to burn, and what happens if your acquisition costs double because you tried to double your marketing spend. Which does tend to happen.

It takes time to optimize and increase marketing spending. When are you going to run at a cash? The last thing you want to do is take investor’s money and ramp everything up quickly. You don’t have time to do it efficiently or effectively. You’re out of cash sooner than you expect. You don’t hit those milestones that you promised that you had in your pitch deck. Now, you’re struggling to raise more capital because you’re out of money faster than what you thought. Running these sensitivities, running this scenario and the financial modeling and forecasting. It’s critical to any business, particularly subscription businesses, because there is a lot of upfront capital to build the subscriber base.

I want to point out something about subscription-based businesses that I’ve learned from a buddy of mine who was in the PE space. They’ve been doing a lot of roll-ups of the guys and gals with truck businesses. You take a pool company. There’s been consolidation of electrical companies. There’s been a consolidation of plumbing companies and whole companies because they’re taking exactly what you were doing from a technology standpoint and doing that with manual labor businesses. If you have pool cleaning, you sign up for a subscription for pool cleaning.

They do that because now they’ve got 10,000 customers that are signed up at $100 a month or $250 a month and they can predictably decipher what their revenues will be like and how they can spend money on marketing and advertising. They can now take that subscription basis to a bank and get debt. There was even a group who is a nail salon group. They have a subscription-based model. There are maybe a couple of thousand in the company. I can’t recall their names, but they do a monthly subscription model where you can get a manicure and a pedicure. It might not seem like you can take this to the level of a business like that.

The same thing is, you can drop in and you can get three manicures or pedicures based on this subscription model, but guess what? You’re only doing about one to two a month. They’re still collecting the money. It’s like a gym. They’re more profitable than they’ve ever been, where like a mom-and-pop isn’t thinking of it that way. Even a mom-and-pop could do that. Now that they’ve got that predictable model. You can take that and say, “We’ve got $100,000 dollars a month they come in. Now, we can go to the bank and say, “I need a $500,000 loan.” The bank knows you’re making this on a monthly basis.

The power of the predictability has so many benefits. It gives you time. It unlocks finance and allows you to make these longer-term investments in a business. The power of being able to plan effectively is impressive and unlocks a lot of capital. The investor base particularly as you get close further away from venture and more into banking, traditional or ventured debt. Its formula eggs. Its formula egg based off your unit economics. You can borrow 4X whatever the metric is.

It is powerful because these subscription business models have proven out over time, whether it’s Netflix or you name it. I watched this movie, a great documentary on MoviePass, which is a subscription business. I don’t know if everybody remembers MoviePass. You could go see unlimited movies or X movies in a month. It’s a great documentary of getting your unit economics wrong.

They went for growth at all cost versus a more sustainable slower growing business model and it’s very interesting. Founders who then took capital then lost control. The people who they lost control of blew the business up, which I didn’t know a lot of that story. If people are looking for good documentaries on subscription business models. It’s an interesting one.

Common Business Mistakes

Talk to me about some of the common mistakes because you’re going down that path talking about that documentary. Let’s lean into that. What are some of the common mistakes that businesses that potentially could be high growth businesses are making in the market?

One of the mistakes that I’ve seen as companies mature, it’s not an exciting topic but it’s how you run your budgeting process or your applying process. Budgeting is not a democracy. It should not be, everybody gets a vote. There’s a great article that Andreessen Horowitz wrote How to Ruin Your Company with One Bad Process and it is about budgeting. For those who have taken part of this, either part of the big company or a small company. It’s all good intentioned. If you want to get feedback, you ask your senior leaders what you need to be successful.

Undoubtedly, what you get back is much more than you can afford because everybody wants more headcount. They start to play games. Some play more than others. “I’m going to ask for ten people because I know I’m only going to get half of what I asked for.” It gets out of control. What ends up happening is you either you agree to all that, you blow up your headcount. You go from 200 to 500 fast. You increase your burn and you don’t get the business results that you expect, which is the worst-case scenario or you end up telling everybody, “Thanks for all that hard work pulling together what you thought you needed, but we can’t afford it.”

In franchise, everybody who’s involved in that process. What I’ve seen be much more successful is a very much top down modeling exercise and exercise done by the finance team, CEO and with a few others. Let’s start with how much cash do we have, how much we can invest in the business, and what we think we’ll get from that? With reasonable assumptions rather than ratios for everything else, a $100 billion business should spend 1% to 2% on hosting costs.

The ratios changed depending on the industry and stage your business but there’s rough guidelines that in a lot of cases you can use. That gives people something to react to and push back on. If they make a good enough case, maybe change some things around the margin. I’ve seen budgeting surprisingly in bad results. It ends in bad results because of the nature of the process. It can also end in bad results because of where you are in the business cycle and the market cycle.

If you’re in the grow at all costs cycle, which up until a few years ago, we had been in for a long time. Since the investors are also pushing you to grow at all costs, you’re looking for anything that will drive growth and you’re willing to underwrite all sorts of things that you may not underwrite in leaner times. It gets you until a lot of trouble because I’ve seen that you don’t have enough runway to execute your business plan. I don’t know about your experience, but my experience is that everything takes longer than people think. I’ve double it at least.

You give yourself a nine-month buffer with an investor and then take that nine months and double it because it’s going to be eighteen months. I’ve seen it in my business, my FinTech business and my real estate business. Everything is taken way longer than I ever expected.

You need to make sure you have enough cash in those scenarios. If you don’t, it’s very tricky because you don’t hit the milestones you need to do that next raise at the valuation you want. You either blow up the business because you run out of capital or you end up taking capital at draconian terms because you don’t have any choice.

One of the things that I want to recap and this is very important for business owners. I want to echo what you were saying. Your standard operating procedures are key to the success of your business, and it’s not just about “This is how we pitch a customer.” “This is how we do our marketing.” “This is how we do our bookkeeping.” It is how all the money flows and who has the say in each department and field of your business. You have to have a standard operating procedure that you stick to because if you get off of the tails. That trains running off the track. Your business can very easily crash and burn.

I’ve seen great examples. It’s in very small mundane processes where things conspirators. It’s how do you approve contracts? What’s the review process? Are you doing competitive bids or not? I’ll give you a good example. You’re in this grow-at-all-costs mentality. You’re pitching the big curve. You’re going to get to 2 million or 3 million customers. That’s what you tell your employees. That’s what they think and that’s what they then go tell their vendors.

They scale contracts to those sizes. Now, you’re paying for your AWS bill to be this huge company well before you get there. Those contracts are very difficult to get out of if you’re not paying attention and making sure. For contracting purposes, let’s be much more conservative on a forecast so we don’t get out too far ahead up our SKIs. We have the right reviews and approvals. Otherwise, you can find yourself locked into your contracts at rates that don’t make sense and are very difficult to get. 

Profitability, Growth, Sustainability

I have found that in my business, and some of the biggest mistakes that I’ve had, to your point, have been getting over my SKIs in terms of either planning for or hiring for expected growth. Not hiring for where I was in the business at the time and accumulated expenses that either harmed the business and slow down the growth or it killed the business lap. You have to be very careful with your expense ratios and making sure that you have in place what you need, especially when you’re in a business that’s in a growth cycle. What I’d love to hear from you is how do you balance short-term profitability, long-term growth and sustainability. Where do you make compromises?

It’s hard in the moment to do this because you’re seeing success. You want to double down on the business. There’s a lot of opportunity. You want to grow as fast as you can. Everybody’s excited. People want to work for growing companies. There’s a lot of momentum that tells you to hire what everybody’s telling you to hire, even though it’s way ahead of the growth curves of where you’re at. One of the things that is important for entrepreneurs and folks running these businesses is to not get too caught up in it.

You have to take a step back and be honest and sober. You’re finding its friends, FP&A and folks who work in this day in and day out can help model through this. What is a scenario where we do double our investments and it doesn’t pan out? What does that end up doing to our cost structure? What does that do to our cashflow? When will you need capital? Making sure that, if that scenario happens, can we survive? How much risk do we want to take?

You can raise money on a big growth story. What I like is to have like gating items. “We have this big growth story.” “Here are the gating milestones that will unlock more investment or more headcount.” That’s a way to one said expectations with investors. It’s like, “This is the plan, but we have to hit these milestones first.” If you don’t hit the milestone, say you miss or few months delayed. It’s a much easier conversation with the investor to say, “We’re not ready to invest your capital yet because we haven’t hit this milestone.” “We’re not at the right payback period.” “We’re not at the right acquisition cost, so we can’t increase investment.”

That gives you time to continue to iterate and not just be like, “We’re not hitting that acquisition costs that we need. We’ll just going to spend more capital to hit the growth profile.” You burn out your capital and you’re in no worse position. Having honest and sober modeling exercises that are internal for your own understanding and understanding your goals? How much dilution do you want to take and risk you want to take that you have to raise capital? What outcomes are you trying to drive at the end of the day?

Let’s say that you get the business to a standpoint where it’s revenue is coming in. I’m going to be careful with using the word cashflowing. I’m just going to say revenue is coming in, and you have an SOP in place. You are seeing growth in the business and you’re looking at taking it to the next level. How do you, as an entrepreneur, look to increase the profitability or the numbers so you can create a higher evaluation for your business?

That answers and the solutions are business-specific, but for me, the process is similar across businesses. One is understanding what drives evaluation because it is different depending on how mature of a company you are or what space you’re in. It could be a multiple of your profit. It could be revenue growth or something totally different. If you don’t have a lot of venture money, this is bootstraps. It is cashflow.

The metric and evaluation differ by industry business. Step one is understanding the metric and what you are trying to achieve. Is it a high-growth venture-backed story where you want to make the investments go public. You have a certain timeline or is it a slower growth but more sustainable and profitable business? You want to sell to a bigger company because you don’t want to take all this capital, all this time and all this risk that is associated with getting a company ready to be at a level to go public. Being a public company isn’t fun for most people.

It’s a lot of stuff that has to happen. Understand what outcome you want to this thing because sometimes, I want a lifestyle business that’s growing healthy and generating cash. I don’t care what Venture Backed or venture capitalists are going to value my company. It’s generating cash for me and that’s enough. Understanding your business, what’s striving the value, and what outcome you’re trying to get is critical.

To me, understanding the financial statements is like where the rubber meets the road. You can have a lot of promising A/B tests. You can have a lot of investor story up into the right charts that are around downloads. If it’s not generating revenue, has a positive margin, and has scalable growth profile. You can see all of this in the financials. The financials won’t tell you what to do, but they’ll tell you where to focus on.

You can compare your financials to what other subscription business lists look like, for example. Do I have a twelve-month payback? If not, why? What’s the biggest reason? Is my retention to low? Are my acquisition costs higher than my competitors? You can start to focus in on what has opportunity for more optimization? Think about what the biggest return on your investment is. I can improve retention by five percentage points. What does that do to the overall physics on the business?

Now, I have to invest less in acquisition to continue than I did before. I can build more referral loops and do other things. Understanding those pieces is important. It starts with financials because you can often see things like my operating costs and my gene. A light on is way out of whack compared to what my competitors or other businesses that are in this space are. You start to peel back the onion. Why is that? Does that make sense for my business? Sometimes., it might make sense.

To me, start there and then understand the drivers and some of the fundamentals in the unit economics particularly for subscription businesses, but others as well. It can give you insights what laborers do I need to focus on and pull to drive the most value and most cashflow at the end of the day, is what you’re hoping for.

One of my mentors told me early on in my career as an entrepreneur that if you don’t have an exit strategy, you don’t have a real business. It’s not that you’re necessarily going to exit the business. It’s that you’re getting from point A to point B, and then you create measurement. He taught me that measurement is based on knowing your numbers and understanding how the inputs impact the output, which impacts your actual margin for your return.

Rapid Fire Round

Those are all the things that create the value for your business. It doesn’t matter whether you’re a tech company with massive scale and hundreds of thousands of clients or you are a local mom-and-pop business. All businesses have value. We’re going to do a segment on valuation and businesses and you should understand that any given point in your time, how much your business is worth. There’s companies out there do that. Know the valuation of your business because It will help drive your business well. Garrett, we’re going to do something fun. We’re going to do a little rapid fire. Are you ready for me? These are questions you don’t know were coming down the pipe could come in. Alright, so fruit smoothie or glass of red wine?

I’m going to go fruit smoothie because I have a newborn.

If you have a newborn, it should be shots of vodka, but no judgment. I would go with red wine.

There’s nothing scary than being a little buzz with a newborn and being worried. That’s why I’m going with the fruit smoothie.

Rabbit or turtle?

Rabbit.

Who would win in a fight, Barbie or My Little Pony?

Barbie.

Why would Barbie win in a fight?

It’s because it was a great movie and I didn’t want Barbie to lose. I haven’t seen My Little Pony in a long time, and I forgot. In my head, you can team My Little Pony. It doesn’t end up in any fights. It’s a discussion.

If you were in a zombie apocalypse, what weapon would you grab?

I don’t know why this question comes up, but it comes up. I’m always like, “I’d like to be the first that dies.” I don’t think I want to survive at all this madness.

That’s a very creative deep dark that may be responsible for us unpacking some other time.

As a parent now, maybe now I feel like an obligation.

Try to save the world. What is your favorite phrase in business?

I don’t know if I have a favorite. I’m just thinking back through our conversation. Unit economics is the thing I said the most, so I’ll go with that. There’s always a lot of lingo in business.

I’ll take it. One book that has influenced you in your career?

I don’t know if we got to this but also Ben Horowitz wrote a great book about his days as an operator called The Hard Thing About Hard Things. I would highly recommend any entrepreneur and business owner to read it. It’s very engaging and a good read. It also has a lot of material and appendices that are very practical, how to hire a good salesperson and what you should be looking for. You want your sales team to be very motivated by money. You want your finance team not to be motivated by my money. Lots of practical examples of advice that he’s seen that I found had resonated well with my experience.

If you are running a business that is doing $10 million in annual revenue and I magically show up one day and give you a $300,000 check. What would you suggest that this business invest in?

That’s a hard question to answer without understanding anything about the business.

Let’s do it again. Let’s say you’re a tech business and you’re providing a subscription service. You’re doing $10 million in revenue or an annual basis. I show up with a $300,000 check. What would you advise that business owner to do to help increase their revenue?

If they have a good marketing engine and in marketing customer acquisition.

Great response. Marketing customer acquisition, I love that. Last but not least, what is the biggest obstacle you had to overcome in your professional career that you overcame and made you who you are?

I’ve had a very winding career. I’m not sure it’s an obstacle, but not getting bogged down in the past year on and pursuing your interests or passion. Even if it feels like a step backwards from a career perspective or financial perspective. It’s unlocked my longer-term career as I look back because I picked things that I thought were interesting. 3D printing sounds interesting. I’ll take a step back and be the first and find in a higher there. I can point to a lot of different points in my career where I took a weird left turn. I don’t regret any others left turns. I’m glad I took the risk and went for it.

I love that. On that note, Garrett Wright, thank you for joining us.

Thank you. I’ve enjoyed it.

Garrett, do everybody a favor now that we had a very fruitful interview. If people can find you or follow you, please let us know what the right platform is for doing so.

I am largely anti-social.

By the way, I own the URL AntiSocialSocialClub.com.

The best place to find me is on LinkedIn. Although you will not find me posting very often, that’s the best place.

I’ll make sure that we get that link. Thank you again, Garrett.

Thank you. I appreciate it. It’s been awesome.

Important Links

• Stash
• The Hard Thing About Hard Things
• AntiSocialSocialClub.com
• LinkedIn – Garrett Wright

About Garrett Wright

Garrett Wright has spent more than a decade working in senior roles across finance, sales, and operations at high-growth, venture-backed startups.
Over the last seven years, he has worked at Stash, the pioneering fintech company with millions of customers that empowers Americans to invest and build better lives. As the first finance hire at Stash, Garrett built and led the finance function during a time in which the business grew from $1 million in annualized revenue to nearly $100 million and raised over $400 million in equity financing.

Currently in the Chief of Staff role, he leads operations and plays an active role driving key strategic initiatives as well as new business development. Prior to joining Stash in early 2017, he served in a variety of roles at MakerBot including Chief Revenue Officer and VP of Finance, during which time MakerBot was acquired by Stratasys (NASDAQ: SSYS) in a $604 million deal.

He also held roles at Accenture and Northrop Grumman. He earned his BS from Ohio State University and his MA from Columbia University.