7 tactics for non-cringy sales

What's up, everyone? This is Alex, the host of Founders Journal. As you may know, I built Morning Brew from my senior year of college until we sold the business in 2020. And now I'm building a variety of businesses in different spaces and different stages. I'm basically averaging 1 to 2 new businesses per year. And because of that, I have had the opportunity to test a ton of different products and services, ultimately landing on a core software stack that serves as my business operating system whenever I start a new company. I have my go-to banking service. I have my go-to formation service. I have my go-to domain hosting service. But probably the most important of them all is my HR service, Gusto. If you're a longtime Founders Journal listener, you know how much I think about people in the context of business. A business is nothing without its people, which means a platform that helps me manage and take care of my people is invaluable. And that means I've tried every HR platform under the sun, always with the same exact goals in mind. First, I want a product that's intuitive and delightful to use. As a non-HR person, I find the intricacies of payroll, benefits, taxes, compliance, and expenses to be painful. So I just want something that makes my life easier. Second, I want it to be affordable. I'm a bootstrapper at heart. I started Morning Brew with $0 and I started StoryArc with $0 as well, which means I don't have infinite dollars to drop on SaaS products. And third, I want a platform that acts as my one-stop shop for all things people. I want it to handle payroll, benefits, hiring, onboarding, and taxes, all while integrating with all of the other tools in my business stack, whether it be QuickBooks, Slack, or Google Workspace. Well, Gusto hit the trifecta, which is why I am a customer and use it for every single one of my businesses. Yes, this is a paid sponsorship by the amazing team at Gusto, but I would sing their praises even if I wasn't being paid to do so. So if you're looking for a platform that takes the pain out of payroll, benefits, and HR, I highly recommend you check out Gusto. And if you sign up at gusto.com/alex, you will get your first 3 months free. Now onto the episode.

What's up everyone? This is Alex Lieberman and this is Founders Journal. For those who are longtime Founders Journal listeners, welcome back. For those who are new to the show, here's the deal. Founders Journal is my audio diary made public for the world. My goal is to increase your odds of success as an entrepreneur by sharing the stories, lessons, and tactics that I experience as I build my businesses. You can expect the podcast Monday and Wednesday with episodes that are under 20 minutes in length. And if you want to get notified when a new episode comes out, make sure to subscribe wherever you listen. Today on the podcast, I'm going to talk about sales, how despite being wildly misbranded, it is the most important tool in an entrepreneur's toolkit, and what my approach and the approach of other successful entrepreneurs has looked like to sell successfully. Now let's get into it. I want you to close your eyes unless you're operating a motor vehicle, and I want you to notice what you see when I say the word sales. Try to actually visualize something. What do you see? Odds are you see someone standing up, holding a phone, speaking aggressively to someone on the other line. And you're not alone. Sales has been in PR crisis for longer than I've been alive, which is an absolute shame because it is literally the most important skill in business. I do not say that facetiously. Sales is king of the hill. Without it, your startup will not succeed. There is a reason that Naval, the founder of AngelList, said, learn to sell, learn to build. If you can do both, you will be unstoppable. Sales is sexy, but it is perceived as slimy. Let me tell you about my journey with sales. At the University of Michigan, sales was not considered to be a sexy skill. I was in the business school. We had one business communications course. Maybe for a third of it did you actually sell anything. The rest of the time was written communication like email and essays. And no one in the business school applied for jobs in sales. Everyone wanted to work in investment banking, consulting, marketing, but you couldn't be caught dead working for some company in a sales role. All of that being said, after 10 years in entrepreneurship, sales is by far and away the most important skill that I have had to use and refine. Literally everything in entrepreneurship is sales. It was sales when I had to convince Austin to go from reader to co-founder of Morning Brew. It was sales when I started growing Morning Brew on Michigan's campus by selling students to sign up for the newsletter. It was sales to get ambassadors on board and pitch Morning Brew on their campuses. It was sales convincing writers to write for our newsletter for free. It was sales convincing our early hires to join our startup, even though there was no sense of stability. It was sales when Austin and I had to convince our investors to invest in 2 college kids who had never started a business before, and we weren't making money yet. It was sales to convince some of the biggest brands in the world to spend hundreds of thousands of Everything at Morning Brew was sales, and it didn't stop with the brew. At StoryArb, I had to sell my co-founder on joining the company and being CEO when the business was tiny. With Growth Pair, my offshore growth marketing business, I had to sell the CEO on why I was worth the equity to become an advisor. So as I reflect on my entire entrepreneurial journey, sales has created every single major unlock in my businesses. Yet sales is wildly misunderstood. On one hand, people associate sales with a used car salesman or a street corner solicitor or Leo DiCaprio in Wolf of Wall Street chest thumping. And then on the other hand, sales has a bunch of different names, and depending on the name that is being used, it is perceived differently. Sales as a word is considered slimy. Storytelling is considered art. Persuasion is considered to be tasteful manipulation. Negotiation is considered to be a serious skill. And then pitching is considered to be a necessary evil in startups. Yet all of these words are all the same thing, and they are all sales. So if you boil it down, sales is as simple as Wanting someone to do something and getting them to do it. We sell at every moment in life, yet we never think about it as an icky thing. Every person who's ever gone on a date or married someone sold them on seeing them or being with them for the rest of their life. Every person who scheduled a meeting and requested a certain day or time sold the other person on doing what was most convenient for them. All of this to say that sales isn't icky. Bad sales is icky because bad sales doesn't feel mutually beneficial, and it feels like aggressiveness is compensating for underwhelming value. Now, I want to share my 7 tactics for good sales, tactics that I've used to recruit, raise money, sell advertisers, and ultimately sell my business. Then we'll finish with sales tips from entrepreneurs that I deeply respect and trust. So let's go through my 7 sales tactic. Number 1, talk very little. In the early days of Morning Brew, I used to speak on sales calls most of the time, and I very quickly realized that my ego was selling. Now I try to speak an uncomfortably small amount, like 20% of a conversation. And when I speak, most of my words are for asking questions of the person I'm talking to. And I'm asking questions to understand how close the person is to making a decision, whether they are the right person to make a decision, and what is the core problem or need that is driving the decision. Number 2, I always start with the sizzle, not the steak. Said differently, I always start by selling the story, not the specifics. And so just to give an example from Morning Brew, one of our biggest brand partners when I was at the Brew was Fidelity. And Fidelity's goal was to attract the next generation of investors who could be account holders with Fidelity as Fidelity was competing against Robinhood and all of these upstart investing platforms. I never would start my conversations with the Fidelity marketing team by talking about the number of subscribers that Morning Brew had or what our click-through rate was or what tactics we could use across our newsletter or other properties to Generate new customers for them. I always focused on telling the story of our subscribers and who they represented for Fidelity, and why that solved Fidelity's problem. I would say to them, "Look, Morning Brew's audience is an entire generation of upwardly mobile modern business leaders. They're high earning, they're coastal, and they are about to make huge life decisions and put their money to work. And they don't yet have the affinity of." an investing platform. They're not yet loyal to Robinhood or Fidelity or E-Trade or, you know, pick your platform. But they are going to be making that decision in the next few years. And you have the ability to insert yourself in the conversation at the exact right time to be picked first by them and to stay with them for the rest of their lives as they invest for the next 50 years. Again, if you think about what I just said there, I didn't talk about anything related to our newsletter. I didn't talk about anything related to our metrics. I just talked about the person that Morning Brew has the attention of, where that person is in their life, what they're looking for, and how that perfectly plays into this specific problem or need that Fidelity has. So again, start with the sizzle, not the steak. Number 3, believe in the thing. Being a B+ seller of an A+ product is a hell of a lot better than being an A+ seller of a B+ product. I always thought I was an unbelievable seller when I was selling Morning Brew. In retrospect, I think I was a good seller, but I think I was selling a great product. And I always came off as confident when selling because I believed deeply in what the thing was that I was selling. I couldn't imagine in 1,000 years selling a product that I wasn't confident would deliver for the customer. Number four, be deeply prepared. I'm going to use an example that isn't sales in the traditional sense, but I think of it the exact same way. Once a year, my co-founder Abby and myself talk about what the one-year plan looks like for StoryArt. And going into this conversation, my goal is to leave no stone unturned. My goal is to anticipate as many questions as possible. And my goal is to critique my own thinking as I think through our 1-year plan and to stalemate my own opinions. So I feel like I have gone through kind of the intellectual CrossFit of planning for our business before ever entering the conversation. And so just for context, before I ever have this hour to 2-hour-long conversation with Abby, I'm working in a Google Doc for probably 6 to 10 hours, Listing out what's going well in the business, what's not going well in the business, what are the biggest questions we need to answer, what changes do we need to make, and with the changes we need to make, where I think those changes could go right, where they could go wrong, and also where any of my current perspectives or opinion on the 1-year plan could also go wrong. I write that all out. And so my view is, I go into this conversation with hours of preparation because, one, Abby deserves that for putting time into the conversation. But two, there is no more effective way to sell my co-founder on the future of the business than putting in the time, the reps, and kind of the intellectual rigor to go through this process with her. Sales tactic number 5, create urgency and FOMO. Classic example of this is in the early days of Morning Brew, I was talking to the CMO of Pottery Barn. And I actually was at the same time talking to the CMO of Restoration Hardware, the other furniture business. And I had this conversation with the CMO of Pottery Barn where I said, look, you already know, I've already convinced you of the value of Morning Brew's audience and how this audience has huge life decisions coming up. They're going to be getting married, buying homes, going on vacation, starting families, et cetera. And you know, they don't have established habits with brands yet. And so, you know, when these people decide to move into a home for the first time, likely the brand they decide to furnish their home with is probably going to be the brand that they decide to furnish all of their future homes with. And look, I don't want to create a sense of pressure or urgency, but I just want to be transparent about the fact that there is another brand we're talking to. And I'll just be 100% transparent that we're talking to Restoration Hardware and we are not going to work with 2 furniture brands because we don't think that's the best thing for our audience. We want to work with one partner in this category that we can authentically recommend. to our audience. And so I just want to, you know, give you at least the best opportunity and all the information you need to make an educated choice about if you want to be that brand. And so this kind of feeling of FOMO where there's almost artificial scarcity created around the category for an audience was incredibly powerful for selling multiple categories at Morning Brew. And again, this doesn't just have to be for advertising. It can be for many other types of businesses. Sales tactic number 6, create a yes ladder. So there's a great book called The Adweek Copywriting Handbook by Joseph Sugarman. And this book is actually about copywriting and how to get people to read to the end of your content. And he has this concept that he calls getting to yes. And the main idea is that when you get someone to say yes, the odds that they say yes again is higher. And then if they say yes twice, the odds they say yes a third time is even higher. And so when I think about sales, I think about how can I get people to say yes to very kind of small asks first? So by the time I am making a bigger ask, like the big sale, they've already said yes 4 or 5 times. And so the example at Morning Brew was always like, okay, do you want to explore what it would look like to partner with a newsletter? And they would say yes. And I would say, okay, awesome. And my assumption is you want to work with newsletters that have at least a 40% open rate and you know, a high average click-through rate. So you're getting good traffic to your website. Is that correct? They would say yes. And then I would be like, and you want to get in front of an audience that's high earning, that is coastal, is that correct? And they would say yes. And so I'd be at yes number 4 or 5. So by the time I'm actually talking about what a partnership with Morning Brew could look like, I've already got them to yes multiple times. And so there's a ton of momentum. So for them to say no is that much harder. The 7th and final sales tactic from my experience selling across my career is that selling does not have to be loud or aggressive. So this is an interesting thing, right? You associate selling with someone who is extroverted, who's gregarious, who's loud. And I actually believe some of the best sellers are introverts. I think some of the best sellers are quiet. I think some of the best sellers just have the best ideas. And I actually find that Being loud and aggressive sometimes means that a seller is compensating for a lack of knowledge or confidence in the thing they are selling. And so what I would say to anyone listening who doesn't view themselves as like a traditional seller, or they don't view themselves as being extroverted, the best sellers that I've met in my career are introverts, and they're the best thinkers. They're the clearest thinkers. They're the people who are the most deeply prepared and thoughtful. And so they don't have to use all of kind of like This theater, this sales theater to convince someone to do something. They just have fundamentally better ideas that they've been more thoughtful about. And so their ideas are all they need to sell something to someone. Now I want to finish with sales tips by entrepreneurs that I trust deeply. First is Jesse Pujji. Jesse is the co-founder of Ampush, which he sold to Red Ventures, and also the founder of GatewayX, which is a venture studio with several successful businesses, including Growth Assistant. He shared 3 sales tips with me. Number 1, getting meetings via a mutual introduction, a.k.a. a warm meeting, is worth 5 cold meetings. Number 2, founders can tell stories, and stories are a huge unlock in sales. And number 3, learning how to meet objections with curiosity versus defensiveness or a quick rebuttal is key. The second expert is Jen Abel. Jen is the co-founder of Jellyfish, which is a consultancy that has helped 300 B2B startups with early-stage sales. Before that, she had senior sales roles at The Muse and General Assembly. Jen has a laundry list of sales learnings, which I'll link to in the show notes, but here are my 3 favorite. Number 1, the quality of your questions is critical for sales discovery. The quality of their questions is critical for intent. Number 2, 80% of early sales is getting them excited by you, the founder, how you see the world, your vision, and how you uniquely solve their specific problem today. And number 3, SMB is not easier than enterprise. And just because that one's short, I'll add on to that, that as we've built StoryYard and I've built a few other agencies now, I've generally found that Every agency feels a general incentive to move upmarket because as you move upmarket, your deal sizes with larger customers are bigger. Larger customers also generally have more budget and more resources. They're more responsive. They're candidly less of a pain in the ass. I generally think the best products for SMBs or early-stage startups are self-service software because I think every agency has a natural bias to work with enterprise customers. And the final sales expert that I trust deeply is Jason Lemkin. Jason is the founder of SaaStr, the world's largest community of SaaS executives, founders, and entrepreneurs. He wrote a great article about being a top sales professional at a software business, which I'll link to in the show notes. But here are a few of my favorites. Number 1, know the product cold. All of it. If you do, you can, if nothing else, add tons of value to your prospects. That alone is probably enough to put you in the top one-third of sales reps. Number 2, be hyper-responsive. Too many reps take a day or even 2 to get back to folks. Now respond in minutes. Prospects truly appreciate it. It is a sign they can see that you actually care about their problem. And number 3, ask who else is a stakeholder, i.e., who else is involved in making the purchasing decision. And go talk to them too. Way too many reps just try to sell to whomever inbounds them. That is it for what has now turned into basically a mini sales accelerator that is just disguised as a Founder's Journal episode. I would love to hear from you. What specific sales tactic or nugget of information did you find most helpful from this episode? Shoot me an email to alex@storyarb.com. That is alex@storyarb.com.

That's S-T-O-R-Y-A-R-B.com.

And let me know. I'd love to hear from you, and I just love getting to know my listeners. Thank you again for listening to Founders Journal, and I'll catch you next episode.