Authors Share Small Business Success Tips from Self-Made Bosses

In this episode of The Workplace podcast, CalChamber President and CEO Jennifer Barrera and authors Jackie Reses and Lauren Weinberg discuss entrepreneurship and share tips for starting and managing a successful small business.

Small businesses are a huge engine in the California economy, but many people start a business without a lot of guidance. Today’s guests, Barrera says, will help provide insights and lessons for small businesses. Authors of Self-Made Boss: Advice, Hacks, and Lessons from Small Business Owners, Reses is the former executive chairperson of software, financial services, and capital lead and head of the people team at Square; and Weinberg is the chief marketing officer of Square.

Self-Made Boss

Weinberg and Reses saw a void of practical and pragmatic advice for business owners on how to start, run and grow their business, which is what led them to write Self-Made Boss, Weinberg says. During the pandemic, they thought a lot about the small business community and the impact that COVID-19 would have on all of them, but they also thought that while there’s a downturn in the economy, usually there is a boom of new business starts.

Weinberg says she and Reses often hear from business owners who want to learn from others and like to share the advice they’ve learned from having their feet on the street.

“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,” she says.

One feature of the book, Reses says, is that it’s written so that the reader can just pick it up chapter by chapter.

“If you need help on HR, you’d go 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,” Reses says.


Reses shares that when someone is going to start a business, there are three things they should do:

  1. Write a business plan. It’s a step that a lot of people skip because they think they know what they want to do. It’s important, however, to put your vision down in writing—even if it’s just a sheet of paper with bullet points describing how you’re going to operate your business. The person should consider things such as: Does it make sense to people? How many employees will be needed? How will I market myself? And, do I have enough cash flow to get through the opening period?
  2. Get the legal and business setup stuff done right up front. You don’t want these things to become a lagging frustration in the future. Be sure to set up a separate bank account and do not combine the business account with a personal account, she warns. Showing that you’re a stand-alone business helps with the finance of the business in the future. The separation of accounts also helps with taxes, infrastructure, and with employees.
  3. Just make it happen. There are a thousand reasons why it’s never the right time to start a business, but you just have to make it happen. Get the support network you need to make it happen; otherwise you’re going to come up with reasons to stop yourself.

Weinberg encourages business owners to embrace the role of technology and automation, such menu QR codes or payroll automation. Although it can be intimidating, modern technology can really save a business owner, especially if they’re not running at full capacity or have any staffing shortages.

Another tip to think about is how one’s services are a representation of one’s brand.

“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,” Weinberg says. “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.”

Lastly, Weinberg shares that when it comes to paid marketing plans, it’s best to be organized. This is something that can be overwhelming, but creating a plan helps. There are many self-service tools and resources available, so it’s important to utilize the tools at your disposal.

When it comes to marketing the business on social media, creating a calendar is something that can help you stay organized. Weinberg suggests picking a few channels where you want to find your audience and then creating a lightweight content calendar that describes, for example, what you will be posting on Mondays, Wednesdays and Fridays.

“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…find the most overwhelming, a lot more palatable,” she says.

Common Challenges, Obstacles

Two recent common challenges Reses and Weinberg see facing small business are gaining access to credit and hiring.

For those who need credit, there are two paths that can be pursued: traditional lending and online lenders.

Reses says that if you go down the path of traditional lenders, it’s important to get all your ducks in a row regarding tax returns and legal documents. Have them in an organized package set in advance. Then, give the package to a few banks and hopefully a relationship can be built.

Online lenders provide a business with different opportunities. This path is great for micro businesses because online lenders can do smaller dollar loans.

“Typically, if your business makes $100,000, $500,000, [and] you need a loan for $5,000, $10,000, $15,000—that’s not the type of loan that typical community banks will offer,” Reses says.

If a business is having a hiring or retention challenge, the business owner should think about the company culture. What culture do you want? What do your benefits say about the company? What do your working hours say? How is your vacation policy relevant?

“The small business owner should really think through all 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,” Reses says.

Business owners can learn more about leadership and listen to free podcasts about how to improve their behavior with their team, how to set up culture, etc. And it doesn’t matter whether the business is an auto mechanic shop, a bakery, or 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,” she says.