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How to Build a $1 Billion Business: 12 Secrets From the World’s Most Successful Startups

Posted: 15 Sep 2019 06:53 PM PDT

By Emily Bauer

Every startup founder dreams of becoming the next unicorn. But what separates the dreamers from the achievers? What does it really take to reach a $1 billion valuation?

Unfortunately, there's no shortcut or magic formula for creating a $1 billion startup pipeline. There are, however, unicorn founders you can look to for inspiration and advice on how to grow your own business. Whether you're a founder, sales rep, or growth hacker, building a $1 billion startup pipeline is a lofty goal. The best way to learn about the keys to unlock unicorn-level growth is to go straight to the source. Study what others have done to achieve crazy growth.

We've gathered tips and advice from founders who launched 12 of the world's most successful startups. These growth secrets offer valuable lessons that you can leverage to boost your business into potential unicorn territory.

1. Don't pitch investors until you have a business worth funding

It takes more than a killer pitch to woo investors. That's why Adi Tatarko, CEO of home design website Houzz, says bootstrapping was "one of the smartest decisions" her company made on its path to reaching unicorn status.

Sure, having investors backing your startup can help fuel your growth by funding new hires, and give you access to a network of mentors and other entrepreneurs. However, going to investors too early can be shooting yourself in the foot.

"Go to investors with a real product with traction, instead of a deck," Tatarko advises. "If you spend the first six months to a year building a great product or service rather than chasing investors and redoing PowerPoints, you'll be surprised how the dynamic with investors will change."

Tatarko and her husband Alon Cohen launched Houzz in 2009 after struggling to find remodeling ideas for their home. They didn't go to investors until they'd already developed "a proven concept with an engaged community and knew how to execute."

Today, Houzz gets 40 million unique visitors every month, including homeowners from 15 different countries.

2. It's OK to keep your day job as long as necessary

Not everyone can afford to quit a salaried job to become an entrepreneur–but that's not an excuse to give up on your dreams.

There's something a lot of people don't understand about building a startup: You don't HAVE to quit your day job to lay the foundation of a successful company. Especially if your job is paying the bills and funding your venture. As a general rule, you should aim to bootstrap first and raise later–if at all.

Take Girish Navani, CEO of eClinicalWorks, for example. Now the CEO of a billion-dollar startup, he bootstrapped his company for two whole years before leaving his day job. Because he held down a full-time job in addition to building his product, he was able to buy himself enough time to thoroughly develop, test, and validate his product and customer base.

His patience and perseverance paid off. Now Navani's startup brings in $300 million in revenue–and it's all privately owned, with no plans for seeking investment or going for an IPO.

It's not easy to balance a full-time job with launching a startup (easily a full-time job in its own right), but it is possible to build a unicorn startup while still working to pay the bills.

3. First-mover advantage is not crucial to success

Don't let competition scare you away from launching your product. Just because a competitor is first-to-market, doesn't mean there's no room for your startup. If anything, an early competitor's success is a good sign that you should continue down your path: It means the market is ready for a product like yours.

For example, Lyft was founded in 2012–a full three years after Uber first disrupted the ride-sharing industry. Although Uber was founded first, Lyft was able to establish a foothold in the market and is now worth a hearty $24 billion.

This is an important reminder that you don't need to be the first company of your kind to be successful. In most industries, there's room for more than one disrupter and the market often responds well to new companies with the right positioning. If you can differentiate by improving upon on existing solution, the market can be very accommodating–especially if there's not a ton of competition yet. That is, you don't need to be first, but you do need to stand out.

4. Focus on growth before profits

For some startups, deciding whether to prioritize on growth or profits can be a bit of a chicken-and-egg dilemma. It's often possible to increase profit margins by making changes that don't necessarily result in growth.

Dheeraj Pandey, co-founder and CEO of Nutanix, wants aspiring unicorns to remember that maximizing profits does not equate to maximizing growth. He reached a $1 billion valuation in 2013 and nailed the formula for revenue growth, despite never turning a profit.

In a 2018 interview, Pandey explained how he quantifies the value of growth versus profit: "We believe that the right balance between the two is measured by the rule of 40. Our revenue growth rate plus free cash flow as a percent of revenue should be at least 40–ours is 49.”

It can be easy to get caught up in the pressure to turn a profit and increase margins–especially when you're reporting to investors who want a fast ROI. If you're backed by investors, it's important to manage their expectations and communicate your goals transparently.

If you're lucky enough to have the resources to bootstrap, Pandey's advice is to resist the pressure to compromise sustainable growth for the sake of a short-term profit boost. In any case, startups shouldn't take drastic measures to maximize profits. Focus on long-term steady growth rather than shortsighted corner cutting to boost profit.

5. Build something you would buy yourself

When developing a new product, always aim to create something you would readily spend money to purchase.

OK, so this tip is less of a growth secret than it is good business sense–but it's still important for aspiring entrepreneurs to see examples of it in action. After all, you can't create solutions to problems you don't understand, and you can't fake passion for something you would never use.

That was the key to New Relic's platform, which is made for engineers, by engineers. Now a $3 billion tech company, New Relic began as a software engineer's desire to find a better way to maintain a working code base and prevent code decay.

Look for problems in your own world and figure out how to scale those solutions to serve an entire industry.

6. Invest heavily in your people

President and co-founder of Eventbrite, Julia Hartz says her top piece of advice for startups is to "really invest in the people."

For the first two years of Eventbrite, the team consisted of just three employees. Once Eventbrite gained a bit of steady traction, Hartz decided her next step should be to focus solely on building an all-star team.

When the company raised its first round in 2010, Hartz realized that if she focused the majority of her time on the people, it could produce results for the company. So, she doubled-down on her efforts by bringing on more people and prioritizing the team's best interests.

She says, "I had a moment where I thought, I wonder what would happen if one-third of our founding team focused solely on people. I thought, I haven't really seen a founder just focus on people and just coming to the table for every major decision thinking about how it will affect people or advocating and amplifying the work of people."

You need to continually seek out the right people and make decisions that are best for the team. Startups without the capital to hire more team members can embody this advice by building connections and networking with mentors, potential investors, and advisers.

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7. Embrace the power of word-of-mouth marketing

Stripe's growth trajectory is impressive even by unicorn standards. Founded in 2010 and launched publicly in 2011, Stripe received Series A funding from a number of investors in the payments industry, including PayPal co-founders Peter Thiel and Elon Musk.

Thanks to these valuable endorsements and connections, as well as its affiliation with accelerator center Y Combinator, Stripe was quickly adopted by a large network of entrepreneurs and developers. From there, word of mouth among developers and founders drove its growth and Stripe became the payment processor of choice for emerging startups.

In a 2012 interview, co-founder and CEO Patrick Collison discussed his reaction to how quickly Stripe initially grew through word of mouth: "That was surprising to us because it's a payment system, not a social network, so it's not something you'd think would have any virality whatsoever. But it became clear that everything else was so bad and so painful to work with that people actually were selling this to their friends."

8. Your end goal doesn't have to be an exit

When VCs invest in a startup, the assumption is often that everyone is hoping for a big exit. But is that really always the case?

Even though the whole industry can seem obsessed with exits, going public isn't the end goal for every startup. In fact, some entrepreneurs actively avoid venture capital because they don't want the pressure to go public. Because how could you not aim to go public if you have VCs in the deal? That's typically when VCs see returns on their investment.

Well, that didn't stop Ratmir Timashev, CEO of Veeam, from striking a deal with VCs even though he planned to keep his business private. Veeam was founded in 2006 and remains privately held to this day. So, how did he do it?

Timashev says a creative deal structure that made it possible to receive funding without planning for an eventual exit. More specifically, he negotiated an investment deal that pays dividends to the VCs.

Of course, his scenario was unusual, because he was able to bootstrap Veeam's initial growth with some of the money he made from a previous venture (which did exit). He encourages founders to think outside the box and be creative when structuring deals with investors.

9. Seek out co-founders with complementary skills

In many cases, before you can raise or make a positive impression on investors, you need to round out your team. Having a solid team, including a technical co-founder, is often crucial to getting investors to take you seriously. In fact, Canva co-founder Melanie Perkins says bringing on a technical co-founder, Cameron Adams, was "absolutely critical" to their ability to raise funding.

"Cam gave us the credibility that we needed to land the investment, but he's also incredibly talented and a genuinely great guy—it's been a privilege working with him for the last five years," she says.

But it's easier said than done. Perkins and her co-founder, Cliff Obrecht, say it took some time and persistence to convince Adams to join their team. Once he agreed to work with them, Adams became the first and only member of their tech team.

"I don't think I ever found the playbook to finding a tech co-founder," says Perkins. "I just kept on planting seed after seed, and in some cases the same seed in different patches of the field, until eventually, eventually, one grew!"

10. Be willing to pivot when necessary

Some of the most successful startups in the world wouldn't exist if the founders refused to change course from their original company vision.

Henrique Dubugras and Pedro Franceschi began dreaming up business ideas together when they met at just 16 years old. Today, they're two of the youngest founders to have reached unicorn territory.

In 2016, Dubugras and Franceschi were students in their first year at Stanford. Shortly after, they joined Y Combinator's accelerator center in the hopes of growing their VR company, Beyond. "I think three weeks in we gave it up," says Dubugras. "We realized we aren't the right founders to start this business."

Fortunately, their experience at Y Combinator helped set them in a new direction. They saw firsthand how difficult it was for founders to gain credit. That understanding, combined with their tech background and large network for entrepreneurs, inspired them to build a solution for startups that needed access to credit.

In April 2017, they started Brex, dropped out of Stanford, and focused on their business full-time. The takeaway here is simple but often difficult to implement–especially when you've invested time, energy, and ego into an initial idea that's just not working out. Be wise enough to pivot when necessary and change your direction to play to your strengths. Stay humble enough that if something is not working, your ego doesn't get in the way of making a change.

11. Remember when your customers succeed, you succeed

Since co-founding Zilingo in 2015, 27-year-old Ankiti Bose has grown her fashion website into a unicorn-size e-commerce business by continually focusing on her customers' needs.

Zilingo first launched as an online marketplace to help small merchants reach more customers. Bose says her initial inspiration came from interacting with merchants selling goods at local markets in Southeast Asia. She saw that there were thousands of sellers who were limited in their ability to scale their business.

The company has since expanded to helping vendors access capital, factories, and technology that makes it easier to purchase materials, manufacture goods, and sell to consumers around the world.

Zilingo continued to grow, in part, because it continued to uncover new ways to help customers beyond its initial offering. The lesson here is to always keep an eye out for new opportunities to differentiate your business and stand out by delivering a better customer experience.

12. Think like a unicorn from day one—(prepare for explosive growth)

Can the advice to "fake it 'til you make it" apply to becoming a unicorn startup? Not exactly.

But you can increase your odds of success by acting like a unicorn from the start. According to Allen Brouwer, co-founder of unicorn startup BestSelf Co., that means building a solid foundation that can support your company as it grows.

His advice for first-time founders is to “build your business as if you were building a $100 million company, not as if you were building a one person start up."

This means developing standard operating procedures that will make it easier to scale your business and grow your team. It might seem unnecessary to document your procedures when your team is small, but doing so allows your startup to scale without losing sight of the approach and procedures that made your early growth possible.

Brouwer says, "Once you start gaining momentum, you’ll wish you had the systems, processes, and hiring practices of the big companies and not the piecemeal processes of a startup.”

RELATED: 10 Lessons for Entrepreneurs I Learned From Being a 'Shark Tank'-Type Judge

About the Author

Post by: Emily Bauer

Emily Bauer is a writer and researcher for Propeller CRM, a simple Gmail CRM solution focused on building pipelines, closing sales, and growing business. Emily is a running and travel enthusiast with a passion for all things writing. Her passions are fueled by Earl Grey, yoga, and tofu.

Company: Propeller CRM
Website: www.propellercrm.com
Connect with me on Twitter and LinkedIn.

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3 Easy Ways to Boost Sales and Finish the Year Strong

Posted: 15 Sep 2019 06:44 PM PDT

You're heading into the home stretch of your sales year, nearing the end of the third quarter, and soon will be starting Q4. What can you do to get some quick sales now? Here are a few sales strategies to help you finish the year strong and meet your sales goals.

Sell differently to speed up the sales process

Face-to-face sales calls take time. Instead of scheduling in-person meetings, why not schedule sales calls by phone to at least start building your sales foundation? Yes, you will find it harder to sell over the phone because you can't see your prospects and they can't see you. But what you're looking for is speed. You have a greater chance of speaking with someone on the telephone than scheduling an in-person appointment with a busy prospect.

Consider a telephone sales call just like you would a face-to-face call. Plan how you will open the call, the questions you will ask, and how you will guide your prospect through the points you want to make or get the information that you need to sell.

Also be sure your presentation is interactive and can be viewed on your prospect’s computer. To reduce the probability of the prospect checking email instead of listening to you, intersperse the presentation with questions that are displayed on their computer screen so that the prospect has to pay attention to you.

Use your existing accounts to sell faster

What takes time in selling? First, it's finding new prospects who need and want what you have to sell. Next, it’s taking the time for prospects to trust you enough so that they will buy from you instead of staying with their current supplier or buying from a competitor.

Existing customers, on the other hand, already know and trust you, and are more open to listening to your pitch and buying from you. So why not call all your existing customers now to see what else you can be selling them? Most salespeople forget that current customers buy other products, too.

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Your existing customers are your best prospects for when you need to quickly put more sales on the books. A good salesperson always finds out what products customers may be buying from other sources to see if they can supply them with the same product, an alternative, or an improvement.

Lost customers can be new customers again

Yes, it does happen. You lose business. And hopefully it happens through no fault of your own. Even if it was your fault, times do change and people learn from their mistakes. Consider talking with your former customer about buying again if the following conditions have occurred:

First, you should have apologized if you caused the problem that resulted in the lost business. If you were responsible, you should have tried to make amends and can't be seriously reconsidered unless you had apologized for what you did. Assuming you did apologize, you can then describe what you will do to ensure the situation doesn't occur again.

Second, enough time must have passed in order for you to be considered again. How much time is enough time? I estimate it has to be at least one year. Consider the time it would have taken for a contract, if there was one, to have been completed with a new supplier. Then try to find out if things are working out between the supplier and your former customer. Your position to earn back the business will be stronger if the new supplier isn't working out.

Third, you must be able to demonstrate what has changed so the situation that caused you to lose the business is no longer a possibility. Has a process changed? Are you now able to identify problems before they cause unfortunate results? Make your former customer aware that things are now different and he or she can be comfortable buying from you again.

You may have heard this quote, "The best time to plant a tree is 25 years ago. The next best time is now." The year is quickly passing and you must act now to get the sales results you want at year-end.

RELATED: Secret to Smarter Selling: Use Your Brain More and Your Mouth Less

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20 Financial Bloggers Share Their Secrets to Running a Successful Blog

Posted: 15 Sep 2019 06:31 PM PDT

The blogging business is booming and the financial space is no exception. Personal finance bloggers often start by documenting their own personal financial journeys and sharing money-saving advice. For some, those journeys lead to a successful business.

For the past decade, the Plutus Awards has been recognizing these creators with an annual ceremony and award season that puts the focus on excellence in financial media. The awards recognize independent financial media voices as well as favorite products and services in the financial industry.

According to Harlan Landes, founder of The Plutus Awards, "It's been really interesting to see how the community of bloggers and podcasters has changed. Many blogs and podcasts have become a lot more sophisticated and marketable." He adds, "People are a lot more concerned with building their businesses and brands, more so than 10 years ago."

Here, twenty of the 2019 Plutus Awards finalists share what they have learned while building their blogging businesses. As with any small business, their paths to success are diverse. Some of the blogs nominated are young, while others have passed the decade mark; some of these entrepreneurs make a full-time living from their blogs while others use theirs to attract clients for other types of services, such as freelance writing or financial planning services.

All have a passion, though, for helping others navigate the often confusing world of personal and small business finances. Here's how they do it:

1. Jackie Beck, founder of JackieBeck.com

“I help people get out of debt without putting their life on hold."

Year founded: 2011

How her blog makes money: Sales of her smartphone app, “Pay Off Debt by Jackie Beck,” and advertising are Beck’s top revenue sources. Others include affiliate marketing (getting paid for recommending other products), courses, and some speaking.

Biggest lesson/challenge: “For me, being part of a community of fellow business owners has been key. This was true way back when I started a wedding photography business, and it's been true ever since I started helping people get out of debt. Viewing other small business owners as community members with similar goals versus seeing them as competition means you approach the world a different way.

“Sharing knowledge and being there for one another benefits everyone involved, especially since our businesses are similar. We know what each other are going through to a certain extent, and can share pitfalls, resources, and successes. There's room for everyone to succeed.”

2. Kelan and Brittany Kline, co-founders of The Savvy Couple

"We help families learn how to budget their money, organize their life, and unlock the freedom to do more of the things they love!"

Year founded: 2016

How their blog makes money: Sponsorships (45%), ads (23%), affiliate marketing (22%), product/course sales (10%).

Biggest lesson/challenge: “To become a successful business owner you need to have excellent time management skills. Over the last three years, we have really put a lot of time and effort into being as efficient as possible in everything we do. Things like using the Eisenhower Matrix, utilizing a project management software, setting up systems for everything we do, outsourcing, and tracking our work hours has been instrumental to our success.”

3. Eric Roberge, founder of Beyond Your Hammock

A blog dedicated to helping people use their money as a tool to live a life they love.

Year founded: 2015

How his blog makes money: Roberge runs a fee-only financial planning firm and the blog supports that business while also helping people who are not clients.

Biggest lesson/challenge: “One major factor in our success is the fact that I was extremely cognizant of our profit margin for a long, long time. Most independent advisors have profit margins around 30%, but until last year we were consistently at 80% or 90%. Staying lean has allowed me to be really flexible and forced me to be innovative. It also has allowed me to build a solid foundation for my personal finances, so that now, as we look to reinvest more in the business and know that our profit margin will start dropping (at least to some degree) as we hire and scale, I feel confident that we can truly afford to take those risks that are necessary to get the business to the next level. It’s much more of a calculated risk because we’re not putting ourselves in a do-or-die situation, and that allows for clearer thinking and less emotional/irrational decision-making.

4. Robert Farrington, founder of The College Investor

A blog offering investing and personal finance advice for millennials.

Year founded: 2009

How his blog makes money: Affiliate marketing, display advertising, brand partnerships, sales of his own products

Biggest lesson/challenge: “For anyone just starting out, I believe there are three keys to online success: 1. Consistency; 2. Creating the best [insert your product/service]; and 3. Time. For an online business, like a blog, creating the best is about creating the best content: written, audio, video. Then, you need to do it consistently—this means multiple times per week, every week. And finally, you need to do it over a long period of time—this means at least one year. If you do all three, you have a high likelihood of success.

5. Kristen Edens, founder of Managing Midlife

A blog that covers "family, finances, and entrepreneurship for the Sandwich Generation."

Year founded: 2015

How her blog makes money: Eden's primary income comes from her content writing services, and she says her blog has "definitely helped me attract business."

Biggest lesson/challenge: “My biggest challenge as an entrepreneur is patience—with myself, with the process, and with building a business. Nothing happens overnight and all those “overnight successes” I admire have had their struggles too. I need to remember that, especially when I get down on myself. Last year while at FinCon18 (a conference for financial bloggers and podcasters), I was mesmerized by all the successful bloggers, YouTubers, podcasters, freelancers, and everyone else who, to me, had the success I craved and needed. It isn’t an easy task as a solopreneur (at any age), and I felt tremendously outclassed.

“Then, while mentoring a first-timer to FinCon, my mentee admitted to studying me online, and right off the bat said, ‘I’m impressed with all that you have accomplished in your life and want to be as successful as you!’ That changed my view moving forward! That statement helped me understand that what we see is not the reality. Entrepreneurship is a lot of hard work, no matter what level you are at.”

6. Tori Dunlap, founder of Her First 100K

“Money guidance from the opposite of an old, rich dude."

Year founded: 2016

How her blog makes money: Speaking and coaching.

Biggest lesson/challenge: “To be a successful entrepreneur, you must serve before you sell. I spent over two years running my business without selling anything—growing my following, gaining credibility, and building relationships. People trusted me, my guidance, and my business, so when I launched, I immediately had sales. I’ve never spent a dime on paid marketing, and 90% of my business comes from Instagram. I’ve focused on providing value and relatable guidance first, and then focusing on making the sale.

7. Ryan Inman, founder of Financial Residency

A blog that "helps physicians conquer their finances."

Year founded: 2018

How his blog makes money: It generates leads to his financial planning business.

Biggest lesson/challenge: “The toughest part is managing the growth and bringing on team members. I’ve had to really understand search engine optimization (SEO)—still working on it!—and I never thought I’d have to try and be an expert in all the ‘other stuff’ other than financial planning. The key is being authentic, not worrying about your ‘numbers,’ and just putting out the best content as possible.”

8. Brian Brandow, founder of Debt Discipline

Blog documents Brandow’s family's journey paying off $109,000 in debt, and offers help for others in similar situations.

Year founded: 2013

How his blog makes money: Sponsored content, affiliate marketing, and ads.

Biggest lesson/challenge: "The biggest mistake I made when starting my small business was trying to do everything myself. It took me some time to realize I needed help. By delegating or outsourcing tasks, it freed me up to focus on the top priority items and grow the business.

“I also believe anyone starting a business would benefit from some type of accountability partner. This keeps them honest and prevents them from digging too deep in every little detail and becoming overwhelmed. A trusted friend, mentor, or mastermind group are excellent sources of this type of help."

9. Pete McPherson, founder of Do You Even Blog

“DYEB” is a podcast and blog that helps content creators grow their impact and income.

Year founded: 2017

How his blog makes money: McPherson runs a membership site for bloggers and podcasters called Online Impact and it is his primary business model. He also earns income from affiliate marketing, and has been a freelance writer and marketer.

Biggest lesson/challenge: “It’s taken me a decade to learn this, but there are two vital skills every business owner needs: Learn how to communicate clearly and sell. Whether you’re monetizing a blog, starting a pizza place, or selling used farm equipment, you will need to communicate exactly what you’re offering. In a digital age littered with ads, if you confuse, you lose. Take classes on speaking and read books on copywriting. The more clearly you can communicate about your product/company, the easier your marketing and sales will be!”

10. Julien and Kiersten Saunders, co-founders of rich and REGULAR

"We document our journey of wealth creation from a black millennial perspective."

Year founded: 2017

How their blog makes money: Affiliate marketing, speaking, and product sales.

Biggest lesson/challenge: “To us, blogging is a form of digital real estate. The greater value we provide our readers, the more visitors we attract and the more lucrative it becomes. We enjoy writing and telling stories, so blogging came naturally to us. However, to do it well is very time consuming and requires absorption of several costs upfront. The best advice we can give anyone looking to launch a blog is to make sure they have 100 topics of discussion they can cover. Otherwise, you may not be able to justify the time, investment, and energy required to keep it consistent.”

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11. Eric Nisall, founder of EricNisall.com

A blog that "talks about the complete picture regarding entrepreneurship and personal finance, not just the sexy side most focus on."

Year founded: 2008

How his blog makes money: Nisall's blog primarily drives traffic to his accounting and tax business, though he says he makes some income from ads.

Biggest lesson: “The most important thing I figured out and impress upon others is to go to the right people— attorneys for incorporating/LLC questions, accountants for tax questions, etc., and not random online people in Facebook groups or websites. I also think a big key is to not look at what others are doing or making because each person and business is unique. What works for one person/business isn’t always going to work for another and oftentimes people only talk about the sunshine and rainbows without mentioning the negatives like self-employment taxes, time investment, etc.”

12. Amy Blacklock and Vicki Cook, co-founders of Women Who Money

A blog dedicated to helping women (and men) take control of their finances.

Year founded: 2018

How their blog makes money: Partnerships with brands (sponsoring our website or individual content, attending events in-person or virtually), services such as content writing and virtual assistant (VA) services, and affiliate marketing.

Biggest lesson/challenge: “Being a successful business owner requires you to take care of yourself and your relationships as well as your business. We've both been guilty of spending a crazy amount of hours at the computer, neglecting family, friends, and our health. When you don’t have enough off time and too little sleep, you’ll get run down, you won’t be as effective in your business, and you may even find yourself snapping at loved ones. While spending lots of hours on your business may help you prosper in the beginning, it will eventually take its toll. Taking breaks, eating well, exercising, and spending time with loved ones will help you stay healthy and to thrive for your business and family.”

13. Bethany McCamish, founder of His and Her FI

"Couple money redefined for those who want to live life differently."

How her blog makes money: McCamish is a freelance writer and her blog helps her land clients. She makes a small amount of money from affiliate marketing.

Biggest lesson/challenge: “Relationships have been key to becoming successful in what I do. No matter what industry you’re in, it matters who you know. Be genuine and authentic. Admit to what you don’t know. I’ve found being vulnerable about skills I wanted to work on allowed me to make even more connections. In general, people were willing to help me out, give me a chance, and still pay me for my work. I grew slowly over time, and I didn’t quit my day job until I could make the numbers work for me.”

14. Jim Wang, founder of Wallet Hacks

A personal finance blog offering strategies and tactics to get ahead financially and in life.

Year founded: 2015

How his blog makes money: Affiliates marketing and display ads.

Biggest lesson/challenge: “You don’t have to have a fully formed, ‘perfect’ business idea when you start. Whatever you start must fulfill a need in the market (or what you perceive as a need) and has to be developed, but what ultimately succeeds may be something different. It’s better to start a business that you think fulfills a need and then tweak and tailor it to the actual need. Don’t wait to perfect something on paper; just get it to a point where it’s ‘good enough’ and launch. Too many aspiring entrepreneurs do too much planning on paper, and opportunity passes them by.”

15. Deacon Hayes, founder of Well Kept Wallet

A personal finance site that helps people make money, save money, and pay off debt.

Year founded: 2010

How his blog makes money: Affiliate marketing, then display ads; sponsored campaigns are a distant third.

Biggest lesson/challenge: “The biggest challenge running a website is keeping up with the constant changes on the internet. At one point Pinterest drove the majority of my traffic. Then their algorithm changed and I had to adapt. I started doing Facebook ads, but then the cost went up and they were not as effective. The key to being successful is being ready (and willing) to pivot when necessary. If I didn’t pivot quickly, it is likely I would have given up years ago.”

16. Kevin Panitch, founder of Just Start Investing

"We make investing easy."

Year founded: 2019

How his blog makes money: Ads, affiliate marketing, and sponsored posts.

Biggest lesson/challenge: “The biggest challenge also happens to be the piece I like most about running Just Start Investing—everything is on you. I own every decision, which is both empowering and stressful. Over the past few months, I’ve found it useful to type up a simple one-line mission statement: Make investing (and personal finance) easy. If my answer or solution to a problem helps drive that mission, then I know I am on the right track. It helps keep the stress down with all these daily decisions!

“If you’re running your own business, my other piece of advice would be to just keep going! Just Start Investing is nowhere close to where I want it to be, and sometimes the amount of work that needs to get done can be daunting. But I just keep chipping away, every day, because it’s fun and I want to see where I can take it.”

17. Andy Hill, founder of Marriage, Kids and Money

A podcast and blog dedicated to helping young families build wealth and thrive.

Year founded: 2016

How his podcast and blog make money: Podcast sponsorships, freelance content development (video; writing), and affiliate marketing.

Biggest lesson/challenge: “As an employee for the majority of my life, I didn’t realize how difficult it was to run your own business. All of a sudden you are managing sales, PR, payroll, IT, and most importantly, accounts receivables. There’s no magic biweekly paycheck waiting for you with a small business!

“I quickly realized that I needed to either slow down or ask for help. Three years later, I decided I would do both. My goal to grow my small business into a full-time career has now transitioned into developing an enjoyable (and profitable) side hustle. Additionally, I’ve connected with some excellent freelancers who can help me with the work that takes me longer or don’t enjoy as much. The slow and steady path feels more comfortable, and lately, I’ve been enjoying small business life a lot more.”

18. Chelsea Brennan, founder of Smart Money Mamas

"A place for women to talk about money without shame or blame."

Year founded: 2017

How her blog makes money: Digital products, online events, advertising, affiliate marketing, and sponsored posts.

Biggest lesson/challenge: “My biggest struggle as a business owner has been learning when to dig in on an idea until it works, when to pivot, and when to pick up a new concept completely. As an entrepreneur, you have so many options, and the roller coaster of ‘This is going to be awesome’ and ‘What was I thinking?’ can sometimes give you whiplash. It’s been important to learn how to step back, ignore what other businesses are doing, and evaluate our progress. What is working? What isn’t? What does the audience think? Then I make choices based on what I’m actively seeing, without letting emotion or ‘shiny object syndrome’ take over.”

19. Robin Rose, founder of Mastering the Side Jam

"A personal journey of paying off debt, making money on the side, following dreams, and aging gracefully."

Year founded: 2017

How her blog makes money: Affiliate marketing and display advertising.

Biggest lesson/challenge: “It’s never too late to learn a new skill, and you’re never too old to make positive changes in your life. I’ve worked in the corporate world for over 20 years (and still do), and two years ago, I decided to start a blog on a whim. It has been the most surprising, interesting, and motivational endeavor of my life. (I know that sounds super hokey, but it really has allowed me to build up confidence and sort of come into my own).

“I still have my structured nine-to-five life, and then in my free time, I have this amazing creative outlet that gives me the opportunity to connect with others. And the fact that I can actually make some money on the side by doing this is the absolute icing on the cake. But I guess the main thing I’d say is: Never discount yourself as being too set in your ways, too far along in years, or too committed to one single thing. If you’re interested in learning a new skill, give it a try and see how it goes. You don’t need to go ‘all in’ at the get-go. Just be open to trying something new.”

20. A Purple Life

A blog that documents the blogger’s journey to retirement by age 30; blogger is anonymous since she has a full-time job.

Year founded: 2015

How her blog makes money: Affiliate marketing, a partnership with a financial services company, and crowdfunding membership platform Patreon.

Biggest lesson/challenge: “There is a strange paradox that seems to exist when starting a business. If money is your main driver—instead of passion—that can often taint your product and content. This is counterintuitive since the main purpose of most businesses is to make money.

“I would suggest that, if possible, don’t place pressure on yourself to be profitable immediately since some types of business, such as blogging, are a long game. Overall, my advice is to do your best, respond to feedback from your audience, and pivot your content or product accordingly.”

RELATED: How to Make Money With Your Business Blog

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