Episode 153: Authors Share Small Business Success Tips from Self-Made Bosses

Welcome to the Workplace, a podcast by Cal Chamber. I'm Jennifer Barrera, President and CEO of the California Chamber of Commerce. And today on the podcast we are placing a special focus on small business. Many of our listeners know that small businesses are a huge engine of the California economy. Nationally, there are 30 million small business owners. In addition, we have so many entrepreneurs in California and, and most of them are involved in small business startups at some point. Unfortunately, too many of them are doing so without a lot of guidance. To that end, we have two great guests here with us today, Jackie Reesis and Lauren Weinberg, who will be providing expertise and tips on how to start a successful small business. Welcome, Jackie and Lauren.

Oh, thank you so much for having us.

So excited to be here. Thank you.

By way of background, Jackie Rhesus is the former executive chairperson of Square Financial Services and and capital lead and head of the people team at Square. And Lauren Weinberg is the Chief Marketing Officer of Square. They've recently written a book called Self Made Advice, Hacks and Lessons from Small Business. This book is a great read on this topic. And in recognition of national small business this month, we thought it would be great to interview Jackie and Lauren to get some insights and lessons for small businesses. So I'm going to start off with a few questions to both of you, Lauren and Jackie. But the first one I wanted to direct to Lauren and ask what led you to writing this book?

Well, first of all, Jennifer, thank you so much for having us on the podcast today. We're thrilled to be here. And I will say that what led us to write this book is that we noticed that there was just a void of really practical and pragmatic advice for business owners on how to start, run and grow their business. And I think we spent time together, Jackie and I, during the pandemic, we walking around and obviously that was the time that we're thinking a lot about the small business community and the impact that Covid would have on all of them. But we also thought that, wow, every time there's sort of like this pause or reset or downturn in the economy, we usually see just this boom of new business starts and entrepreneurialism. And I think that was true with COVID and then with the great resignation. And so Jackie and I thought it would be the perfect time to put something out there that would be just, just giving advice to people who are getting started or who are already in business. And part of this came from a few insights. I would say. We know business owners want to hear from each other because they in our. Both of our capacities at Square and in Jackie's role now, like, we hear that all the time. They just want to learn from other people who have been there and done that. The way that they talk about the advice that they have to give and just comes from their place of just like feet on the street, they've been there before. And to be honest, there's no reason why every small business owner or entrepreneur needs to feel like they're reinventing the wheel when there's just so much incredible insight and wisdom that can be shared from these business owners. And so we wrote the book because we thought we could package all of that up in a way that would feel really approachable and different from other things that exist in the market and hopefully help all of these business owners that already exist. And we're about to get started.

One thing to know about the book also, because I think it's relevant for the audience, is that it's written so that you could pick it up chapter by chapter. If you need help on hr, you can read the HR chapter. You need help on marketing, you read the marketing chapter. And it's not boring. It's told through the eyes of business owners and listening to their stories so that you hear it through the lens of someone else's narrative and experience. So it's very approachable and understandable. And we talk through a lot of businesses a lot in California. And when you understand how they sought through their problem, like, huh, how did someone think through.

Reboxing their mail order olive oil at Shabika's Olive Oil, you get this dynamic of like, oh, interesting. If I think through my workflow like that, what should I change? It's only through learning through that experience. But the other thing we did is we combine the experience of these stories with a framework from experts in their field. So that when we talk about writing a business plan or we talk about operations, you hear from both the business owner as well as the expert combined together to make it kind of easy, approachable, readable, quick, kind of funny. In a lot of ways.

It'S an easy read for people who are trying to pick up some hacks.

So in your interviews with these businesses, when you were writing this book, were there three tips that you would provide or that you can highlight that you were able to identify through your interviews that you could share with the audience today of successful small business owners? Three tips for that or somebody who's considering opening a small business.

So I'll start on the beginning, and then Lauren should Go through other tips that might be interesting because I think some of the marketing advice is super instructive and helpful to anybody. I know. I learned a lot from it. But when you're going to start a business, I think there are three things a business owner should think through and they're really simple. The first is writing a business plan. So a lot of people skip this step. They think they know what they want to do. Even if you write it on a one page piece of paper and write out bullet points of how you're going to operate your business, I think it's a very clarifying experience to actually put your vision on a piece of paper. Can you say it? Does it make sense to people? And then when you actually start to fill in, like, how are we going to operate? How many employees do I need? Is that feasible? How am I going to market myself? And do I have enough cash flow to get through the opening period? I think that helps you answer a lot of questions as to how you need to do it, what help you need, what resources you got to line up. So I would absolutely write a plan. The second thing that I would do.

Is to just make sure you get all the legal and business setup stuff done right up front so that it doesn't become a lagging frustration in the future. Did you set up a separate bank account? Do you? And a lot of people usually don't. As a sole prop, for example, they combine their business account and their personal account. And I highly recommend not doing that. Like set up the infrastructure so that you could show yourself as a standalone business. It helps you finance your business in the future, helps you with taxes, it helps you with infrastructure, it helps you with employees. But if you go through the steps of getting the legal and the finance done, it'll just help you for the long term. And trust me, I just set up my own business. It's really frustrating and it makes your head spin, but you got to do it. And you could go get resources online, you could call friends that you know can help you, but absolute necessity. And the third thing, there are a thousand reasons why it's never the right time to start a business. You got to just make it happen. Get the support network you need, make it happen and just go for it. Because otherwise you're going to come up with reasons to stop yourself. And so I think you got to just have a conviction in your beliefs and your vision and make it happen. Then I'll turn it to Lauren.

Yeah, I agree with what Jackie said. I would add a couple of things. One is I would really encourage business owners to embrace the role of technology and automation. I think it is something that can feel really scary. But if you think about some of the challenges that are facing business owners today when it comes to staffing, being able to leverage technology, whether that's QR codes, if you own a restaurant, automating your payroll, send, there's so many different use cases for how technology can come in, can really save you as a business owner from not being able to run at full capacity if you have any staffing shortages. And so I think there's this fear of technology that exists for a lot of business owners that have been around for a long time. And I would say like embrace technology and the role that it can play because I think at the end of the day can really save you a lot of heartache. So that's one. I think the second thing is the much more marketing specific tip which is every interaction that somebody has with you, your products or your services are a representation of your brand. And so no detail is really too small. And I know business owners have a lot to contend with. But I would just say that if you make it your goal as a business owner to create really special experiences and products and services and you tell the story of why you're in business, people are going to want to continue to be in business with you. They're going to talk about it to their friends and earned media and creating that organic flywheel is the best kind of marketing you can do. And then the last thing I'll say is when it comes to your paid marketing plan, I would say just be organized, create a plan. I think it can feel really overwhelming. So I will say to all of your listeners that there are so many self service tools and resources that are available. I know that it can feel really overwhelming. But when it comes to paid marketing platforms, they all have really good tools for small business owners. So I would just encourage people to take advantage of what already exists. But then think about your audience, where they spend time and, and where you want to find them and then pick your few channels so you're not trying to be on all of them that you know will really resonate with your audience and then just create a very.

Lightweight content calendar. Mondays, I'm going to talk about this. Wednesdays, this, Fridays, this. Then you have three days a week you know what you're posting and I think it takes away a lot of the like writer's block or sitting down and not knowing what you want to do. And you can talk about your story in one of your posts. You can talk about your employees, you can talk about a community event, you can talk about your products and services or a special promotion. And I think just sitting down and creating that calendar and getting yourself organized makes the task of marketing your business, which is one of the things that business owners, I think, find the most overwhelming a lot more palatable.

Those are some really good tips. Thank you so much for sharing those. In your interviews and your research, was there any common theme with regards to challenges or obstacles that was common amongst all small businesses that they were facing? You know what I mean? Maybe some of the advice that you just provided on how to overcome it, but just curious if there was any common themes with regards to the obstacles.

You know, the place where we saw a lot of challenges right now are twofold. One is gaining access to credit forever a challenge for small businesses. And the second is around hiring right, right now. And I'd say on gaining access to credit, and this is something that we deep dive into, say there are two paths to pursue. One is traditional lending. The other is online lenders. If you go down the path of traditional lenders, we talk about like just getting all your ducks in a row with regard to your tax returns, all your legal docs. And I would pull it together in an organized package so that you have it in advance. And then I would go and I would give it to a few banks and kind of go. You could hopefully build that relationship. And we talked through this in a lot more detail. But if you put it together in one organized pack in advance, you're done. You could copy it five times over or send PDFs, you're good to go. And you did the burdensome work already upfront. The more interesting path though, and this goes back to what I said about setting up your company.

As a business, is that there are a lot of opportunities now with online lending that are great for micro businesses because they'll do small dollar loans for small businesses. And typically if your business makes $100,000, $500,000, you need a loan for 5,000, 10,000, 15,000. That's not the type of loan that typical community banks will offer. And so at the scale of these loans, they're often very appealing from online lenders. Those online lending sources could be tax software, point of sale software, and different systems that you interact. American Express has a great small business lending program. And so there are lots of opportunities to do it with two clicks of a button based on your own experience in a business context. So that the opportunity now is so great to have it at your fingertips. So that's financing. That's the quick version. On the HR side, I think the dynamic businesses are going through is extraordinary right now. And our advice to small business owners in trying to deal with retention issues is to actually think through the culture of the company they're building. And a small company might not sit there and say, what culture do I want? What are my benefits say about me and who I'm doing? What are my hours say, how is my vacation policy relevant? And the small business owner should really think through all of these and think about what they're telegraphing to their employees, who are a really important constituency for their operations, and make sure they're putting their best foot forward as leaders. Do they need to learn more about leadership and listen to free podcasts about how to improve their behavior with their team, how to set up culture? It doesn't matter whether you are an auto mechanic shop, a bakery, a huge restaurant, you still can create an environment that is very proactive and thoughtful in building a company so that employees want to stay there. They want to appreciate that you've got their back, that they're going to learn something, and that they're inspired, because those are the types of things that are important to employees today.

Yeah, I second, of course, what Jackie's saying. I don't think there's ever been a time like right now. And the fact that business owners of all sizes, not just big companies, need to be thinking about benefits and culture is, I think, just something completely new and different. And so I think, going back to your initial question, though, the biggest challenges I think are, are the same tried and true one that have been around forever, which is just not enough time in the day. I think business owners wear so many hats, and so there's just. They're always pulled in a million directions, which is why I said they should really embrace, like, automation and technology. But now it's even like the demands on their time are even greater now than they ever have been. Because it's not just about hiring people to work in your business. It's about thinking about a culture and a retention strategy. And these are things that business owners just didn't, or like smaller business owners, didn't have to worry about as much as they do now. So I would say that's a big one. I think marketing is always challenging just because it feels really overwhelming. And you could spend all your time in every day, every day just thinking about marketing, thinking about content, posting on different Social channels, which is why I suggested a few things to break it down. And then I would say that the new, the other challenge that's new and different is business is just less predictable than it used to be. There's been a number of just curveballs thrown in business owners direction. You know, obviously the shutdown was one thing, but then there was supply constraints. And we had business owners in the retail space who are all of a sudden trying to think about where they're going to get their inventory and having to get warehouses to store inventory because it just, they didn't have a reliable supply chain anymore. So that one was new and different. And it's just been literally one thing after the next where, you know, there's Covid. What are the right protocols? Do you need to have like protective gear in your business? So I would say just, just so many things that have come in the face of the pandemic in terms of just like not really being able to have as much certainty around your revenue streams, I think has been challenging, but it also has been, it's provided a lot of tailwind for a lot of people as well. Because people, people got really scrappy because I would say one of the things about business owners is that they are so resilient. And so when Covid came, people found different revenue streams and when the world opened back up, they had multiple revenue streams. So in a lot of ways it's been a really great accelerant, but it still goes back to the fact that they wear a lot of hats. There's not enough time in the day. And I think just trying to make it all happen is still the biggest challenge for a business owner.

Absolutely. It is a huge testament to those business owners who were able to be resilient and make it through all the challenges that of course the pandemic threw at them. And now coming out of it, the supply chain issues is a big problem obviously that so many businesses are facing, but certainly the impact to small businesses is significant. With that, I will just ask, as we are getting ready to close out, if there's any final tips or comments that you want to make regarding your book or small businesses before we close out. And Jackie, I'll put that one to you first.

Yeah. So I had the pleasure of traveling and meeting a lot of small business owners while I was at Square. And I was constantly inspired by the grit and the brilliance of people running the companies across Main Street America. And I know in the pandemic I started rooting for my local tailor and my dry Cleaner and my nail salon. And I think now is a time where that authenticity and that relationship with your customers really matters. They kind of emotionally connected in these last few years. And so I know my inspiration has made me more focused on being small business proud. And I think there is something there to appreciate with the tenacity and brilliance of those who are proceeding down this path of entrepreneurship. I guess a shout out to everyone who's making it happen and also a great deal of appreciation. I hope they embrace this moment in time to enjoy that connectivity because I know that the feelings that I certainly have for my local community are shared by a lot of folks I know across the country. And so more power to you.

Yeah, I couldn't agree more. Thank you to everybody who just I think weathered an incredible storm and really showed up for all their communities. I think the only thing I would maybe add to what Jackie said is and not to really be plugging the book, but I will say I ran a business before I went to Square and if you're thinking about this book, but thinking I don't know if I have any time, I just wanted to reiterate one of the points that Jackie made, which is if there's just one topic you're struggling with, you can pick up the book and read that one topic and think about going back to the other things later. You do not need to read it from beginning to end. And at the end of every chapter we give the readers a few questions to think about so that you can think about the experiences that you've read about from other business owners coupled with what the experts have said and then how you would apply it to your own business. And so it's really a different concept, I think than what people are used to seeing from like a small business advice standpoint. And so I just wanted to say that we designed it to be really approachable and easy and actionable and so, and, and, and also fun. We tried to make it really fun by sharing just amazing stories of some of the business owners that we really.

Admire and respect a lot in California. Actually, we have a good handful in California.

That's fantastic. Our California small businesses are obviously super important to our state's economy and we're happy to see them continue to thrive post pandemic. And I'm just going to give another shout out to the book with the title. It's again titled Self made Advice Hacks and Lessons from Small Business. I want to thank Jackie and Lauren for being here with us today and thank all of our audience for joining us on the Workplace. Please comment, share and subscribe to Cal Chambers podcast by visiting calchamber.com thanks again.

Thank you.

Thanks.