Table of Contents
Entrepreneur Laura Rolla reveals how she built multiple businesses to reach $15 million net worth while prioritizing lifestyle over endless growth. Discover her $5 million financial goal strategy, the philosophy behind "lifestyle businesses," and practical insights on finding contentment without getting trapped in the wealth accumulation treadmill.
Key Takeaways
- Time Freedom Over Income: Laura prioritized schedule control over maximizing earnings, recognizing that time flexibility often provides more life satisfaction than additional income.
- Set Clear Financial Targets: Her $5 million goal using the 4% rule provided a concrete endpoint, preventing endless accumulation without purpose.
- Design Businesses for Your Life Stage: Laura consistently chose business models that aligned with her evolving life priorities, especially around having children and family time.
- Pay Yourself Throughout the Journey: Rather than sacrificing personal income for business growth, Laura maintained consistent salaries that supported her desired lifestyle during the building phase.
- Use Constraints as Design Tools: Planned maternity leave forced better business systems and reduced founder dependence from day one.
- Money is for Exchange, Not Accumulation: Laura maintains that money's only purpose is to trade for experiences, purchases, and lifestyle elements that bring joy.
- Lifestyle Business is Valid: Despite startup culture's bias toward high-growth models, businesses optimized for lifestyle support rather than maximum scaling can provide superior life satisfaction.
- Define "Enough" and Stick to It: Having clear parameters for financial sufficiency prevents the endless treadmill of always needing more.
- Simplify When You Reach Your Goals: Laura chose simple investment strategies and avoided lifestyle complexity that would require more wealth to maintain.
- Work Can Continue After Financial Independence: Achieving financial freedom doesn't require stopping all work—it enables choosing work for fulfillment rather than financial necessity.
Timeline Overview
Laura's Financial Foundation (03:54) How Laura's upbringing with financially savvy parents who had different money philosophies shaped her balanced approach to wealth and spending.
Balancing Lifestyle and Financial Goals (07:14) Laura's realization that time freedom was more valuable than traditional career success, and setting her initial six-figure income goal.
Starting and Scaling Businesses (13:21) From freelance graphic design to online courses, B-School partnership, and building Edgar into a million-dollar SaaS business.
Selling the Business and Life After Exit (19:13) The process of selling Edgar for "single-digit millions" and reaching her $5 million liquid target, plus immediate lifestyle changes.
Lifestyle Business vs. Growth Business (21:41) Laura's perspective on why businesses should serve lifestyle goals rather than pure growth, and defending the "lifestyle business" concept.
Laura's Investments and Expenses Breakdown (24:18) Detailed breakdown of her $15M net worth, investment strategy, monthly expenses, and spending priorities including extensive family travel.
Balancing Work and Personal Life (30:09) How Laura continues working on Paper Bell part-time while maintaining focus on family and lifestyle rather than aggressive business growth.
Avoiding the Comparison Trap (32:54 ) Strategies for staying grounded when surrounded by entrepreneurs achieving higher financial metrics and avoiding the endless pursuit of "more."
Final Thoughts on Wealth and Happiness (36:33) Laura's philosophy on money as an exchange tool, the importance of defining "enough," and why happiness doesn't scale linearly with wealth.
How Do You Stop Hustling When You've Already Won?
Laura Roeder told herself that at $5 million liquid she could live the life she wanted and refocus her life on what matters most: living. Unlike a lot of entrepreneurs who get caught up in the game and keep chasing more, Laura stayed true to that goal and quit hustling harder than she had to. But how did she avoid the endless treadmill for more?
What if you could build a business that supports the exact lifestyle you want—and then actually stop when you reach that goal? Most entrepreneurs get caught in an endless cycle of growth, always moving the goalposts higher. But Laura Rolla did something different.
Starting with a $28,000 salary in Chicago, Laura set a clear target: $5 million in liquid assets following the 4% rule to generate $200,000 annually. Today, with a net worth of $15 million, she's achieved that goal and chosen to focus on lifestyle over accumulation.
Laura, founder and successful SaaS entrepreneur, shares her journey of hitting her financial target, choosing simplicity, and focusing on what matters most. With a net worth of over $15 million, she explains how she prioritized lifestyle over accumulation, and how her upbringing played a key role in shaping her financial mindset.
In her story, Laura discusses how she hit her financial goal and resisted the temptation to keep pushing for more. You'll discover her business philosophy, why she believes in running a business for lifestyle and not just growth, and the importance of knowing when enough is enough. Plus, she reveals her personal investments, expenses, and how she balances wealth with family time.
Laura's journey from graphic designer to serial entrepreneur offers a masterclass in intentional wealth building. She's built and sold multiple businesses—from online courses to a SaaS company that hit $1 million in recurring revenue within 11 months. But what makes her story unique isn't just the financial success; it's her philosophy of building businesses to support life, not the other way around.
Laura's Financial Foundation
Laura's healthy relationship with money started early. Her parents provided a unique blend of financial wisdom—her father appreciated quality items like Mercedes and mid-century furniture, while her mother embodied extreme frugality, reusing plastic bags and finding treasures on "big junk day" when neighbors put large items on the curb for trash collection.
"I was very lucky to get a really solid financial foundation," Laura reflects. "My parents are great with money—they told me things like never have a car loan, always just get a car that you can afford to pay in cash, never have any credit card debt."
This foundation proved crucial because Laura didn't have the typical entrepreneur's "chip on the shoulder" motivation. "Sometimes you hear entrepreneurs being like, 'I'm motivated by my dad abandoning me or I have this chip on my shoulder'—I am not motivated by that, which I think I'm grateful for."
Practical Insight: Establish clear financial principles early. Simple rules like "no car loans" and "no credit card debt" create boundaries that prevent lifestyle inflation and debt accumulation.
Balancing Lifestyle and Financial Goals
Laura's entrepreneurial journey began with a lifestyle revelation, not a business idea. Working in Chicago for $28,000 annually, she couldn't take time off to hang out with her visiting friend because of rigid work schedules and limited vacation days.
Meanwhile, her actress friend in LA—despite working restaurant jobs—had complete control over her schedule. "She had tons of time for you... she could hang out with me during the day, she'd be like 'I'll just do an extra shift the day before you come.'"
This contrast sparked Laura's first epiphany: time freedom was more valuable than a traditional career path. She approached her boss about going part-time to start her own clients, but when her boss said, "If you go part-time, everyone will want to go part-time," Laura knew she had to quit entirely.
Her initial financial goal was simple: reach six figures annually. "I definitely wanted to make six figures, which is funny because I think that's still like—everyone who starts as an entrepreneur, it's still the same goal: get to six figures a year."
Practical Insight: Identify what lifestyle elements matter most to you before building a business around them. Time freedom often proves more valuable than higher income with less flexibility.
Starting and Scaling Businesses
Laura transitioned from employee to freelance graphic designer, then pivoted into social media consulting as platforms like Twitter emerged. This was the early 2000s, well before social media exploded into mainstream business use.
Her first online course about Twitter generated $3,000 from a single promotional webinar. "I used to hustle to get one client for $3,000, and now I just did a live promotional webinar to sell it and made the money. I was like, this is amazing."
The course business quickly scaled to six figures in the first year, but Laura already recognized limitations. Course businesses are typically built around the founder's personal brand, making them difficult to scale beyond the founder's direct involvement.
B-School Partnership and Strategic Exit
Laura co-founded B-School, an online education business, with a partner. The business grew rapidly, but Laura realized it wasn't her calling. "I liked it but I didn't love it," she explains.
More importantly, she was already thinking strategically about her future. "I've always known that I wanted to have kids, so I'm like, I'm going to have kids in the future—I want a business that I can take a lot of time off from and isn't relying on me."
Laura sold her stake to her co-founder, using the proceeds to buy a house in Venice, California. While financially successful, this exit didn't reach her ultimate $5 million goal, so she began planning her next venture.
Building Edgar: The Perfect Timing
In 2012, Laura met her future husband and business co-founder. They launched Edgar, a social media management software, in late 2014—just months before their son was born in January 2015.
"I always joke that everyone should go on parental leave right after they launch a business because it was an amazing forcing function that the business had to not rely on me."
This constraint proved brilliant. From day one, Edgar was designed to operate with a team rather than depending on the founders' constant involvement. Laura went on maternity leave knowing the business had to survive without her, creating systems and processes that would serve them throughout the company's growth.
Edgar's growth trajectory was remarkable. The company hit $1 million in annual recurring revenue just 10-11 months after launch, while Laura and her husband maintained their target salaries of around $200,000 each ($300-400,000 combined before taxes).
"We had always paid ourselves really well along the way," Laura explains. This decision reflected a core philosophy: "If your business is having financial troubles, the owner should not be the first to go... the whole point of the business is to pay you."
By 2019, Laura was ready to complete her journey to the $5 million goal. "I was like, no, I just feel ready to be complete with it and be done with it entirely." The sale process took six months from decision to close, with Laura and her husband retaining 100% ownership (minus taxes) of the "single-digit millions" sale price.
Practical Insight: Look for business models that can eventually operate without your constant involvement. Use constraints to force better business design, and evaluate business opportunities against your long-term life goals.
Selling the Business and Life After Exit
"We had always paid ourselves really well along the way," Laura explains. This decision reflected a core philosophy: "If your business is having financial troubles, the owner should not be the first to go... the whole point of the business is to pay you."
By 2019, Laura was ready to complete her journey to the $5 million goal. "I was like, no, I just feel ready to be complete with it and be done with it entirely." The sale process took six months from decision to close, with Laura and her husband retaining 100% ownership (minus taxes) of the "single-digit millions" sale price.
Hitting the $5 million liquid goal fundamentally changed Laura's relationship with money and work. "The only point of the money is to exchange it for other things," she emphasizes. "It's easy to get caught up in growing the money, but the only point of growing the money is to trade it for the pizza and the hotel room and the after school club."
Post-sale, Laura and her family redesigned their lives around travel and time together. They spent six months traveling full-time as a family, including a month in Japan when their son was two and later extensive European travels.
"Last year we spent six months traveling full-time as a family... it made our family so much closer and our kids so much closer to each other. It's where our family feels our true selves."
Practical Insight: Pay yourself appropriately throughout your business journey rather than sacrificing personal income for business growth. This builds lifestyle sustainability and prevents the need for dramatic adjustments post-exit.
Lifestyle Business vs. Growth Business
Despite achieving financial independence, Laura and her husband launched Paper Bell, another SaaS business. This decision might seem contradictory, but it reflects Laura's nuanced approach to work and purpose.
"I'm trying to bring back the term 'lifestyle business,'" Laura explains. "What is the point of having a business if it's not supporting the lifestyle that you want? I just genuinely don't get it—just get a job if you don't care about having control over your lifestyle."
This philosophy challenges the startup world's bias toward high-growth models. In Laura's view, businesses optimized for lifestyle support rather than maximum scaling can provide superior life satisfaction. The key is designing work around your priorities rather than letting work define your life.
"I check in with myself regularly... some days I wake up and I'm just like, I'm ready to sell this today, I'm done with this. But I'm like, oh, but I want to see—we have this project coming up and I want to see where... we haven't tried this thing yet. That shows me that I am still enjoying it."
Paper Bell generates about $12,000 monthly after-tax income combined, while they work part-time schedules. The business operates as a true "lifestyle business"—profitable, sustainable, but not optimized for maximum growth.
Practical Insight: Financial independence doesn't mean retirement from meaningful work. It means having the freedom to choose work that aligns with your interests without financial pressure.
Laura's Investments and Expenses Breakdown
Laura's current net worth sits around $15 million (excluding her current business), but she remains committed to her original philosophy of "enough." Her investment strategy is deliberately simple:
- 50% Vanguard US fund (VTI)
- 25% Vanguard global fund (VXUS)
- About $1M in bond funds
- Small allocations to REITs and dividend funds
- Multiple real estate properties totaling about $4M
Her monthly expenses reflect her priorities around family and experiences:
- $3,000 mortgage (on $2M house, mostly paid off)
- $700 other house bills
- $1,000 groceries
- $900 eating out
- $200 kids' activities
- $300 weekly house cleaning
- Major travel expenses (e.g., $25,000 for a month in Spain)
"I had to look this up for this interview because I had absolutely no idea what my monthly expenses were. I actually didn't even know how much my mortgage was because that comes out of my husband's account," Laura admits. This casual relationship with money tracking reflects her confidence in having "enough."
Balancing Work and Personal Life
Laura's approach to work-life balance challenges traditional entrepreneurial narratives. Rather than grinding toward some future reward, she designed her businesses to support her desired lifestyle from the beginning.
"Something I always say is like keep your eyes on your own paper. You know, what other people have done really has nothing to do with me like they're not living my life," Laura explains when discussing how she maintains perspective in competitive entrepreneurial environments.
Her family's extensive travel demonstrates this philosophy in action. They've taken months-long trips while maintaining their business operations, proving that work can serve life rather than dominating it.
"We've gone on and off with that stuff over the years," Laura says about hiring help like chefs and assistants. "I think people tend to view that stuff as like a black and white or kind of a step up in your life... we always try to really check in with like what feels good for this stage of life."
Practical Insight: Design your business and lifestyle to evolve together. What works at one life stage may not work at another, and that's okay—adjust as needed rather than locking into fixed patterns.
Avoiding the Comparison Trap
Being surrounded by successful entrepreneurs creates constant opportunities for comparison and the temptation to always want more. Laura has developed strategies to maintain contentment despite being in communities where others achieve higher financial metrics.
"I try to remind myself that everyone's journey is different and a lot of it is luck," Laura reflects. "When you... it's luck, it's motivation, it's purpose so it's like we're all on different paths, we're all on different journeys, we've all made different choices."
She's also observed that wealth doesn't automatically create happiness: "I've been lucky enough to know a lot of really wealthy successful entrepreneurs and I've just been able to see firsthand that a ton of money does not add happiness to your life. Enough money to not have to worry about money is huge... but adding extra houses or having a $20 million house instead of a $2 million house... not only does it not increase your happiness, it often comes with massive downsides."
Laura finds that being a woman in entrepreneurship actually provides some advantages in this area: "Something nice about being a woman is I find a lot of women are more willing to talk about it... there's so much talk about like 'I feel like I just want to kind of step away from my business for a year and I've given myself permission to do that.'"
Practical Insight: Recognize that comparison is inevitable but not useful. Focus on your own journey and remember that more wealth often brings more complexity without proportional happiness gains.
Final Thoughts on Wealth and Happiness
Laura's philosophy boils down to a simple but powerful concept: money is for exchange, not accumulation. "The only point of the money is to exchange it for other things," she emphasizes. "It's easy to get caught up in growing the money, but the only point of growing the money is to trade it for the pizza and the hotel room and the after school club."
This perspective allows her to spend confidently on what matters while avoiding lifestyle inflation in areas that don't bring joy. When considering purchases, she and her husband ask themselves: "If we have the money we should spend the money because we never miss it later... once the money's gone it's gone and it's fine because we can afford it."
Laura's approach to the wealth and happiness question is refreshingly direct: "You only get one life... I don't want to die today but I want to feel like yeah if I died today I was happy with the choices that I made, I was happy with where my life is."
She rejects the common entrepreneurial narrative of grinding now for future rewards: "I'm so not a believer in this entrepreneur thing of like oh yeah you're going to hustle and grind for five years but then it's going to get better. It's like do those five years of my life not matter?"
Instead, Laura advocates for intentional living at every stage: designing businesses and lifestyles that create satisfaction in the present while building toward future goals. Her story demonstrates that it's possible to build significant wealth without sacrificing life satisfaction—but only if you're clear about what "enough" means and stick to that definition.
Practical Insight: Define what wealth means to you beyond just accumulation. Focus on creating a life you enjoy today while building for tomorrow, rather than sacrificing present happiness for future theoretical rewards.
Conclusion
Laura Rolla's journey demonstrates that entrepreneurial success doesn't require sacrificing life satisfaction for business growth. By maintaining clear priorities around lifestyle, family, and personal fulfillment, she built multiple successful businesses while avoiding the common trap of endless accumulation.
The key insight from Laura's approach is that business should serve life, not the other way around. By defining what "enough" looks like early and designing businesses around life priorities rather than maximum financial outcomes, entrepreneurs can build sustainable success that enhances rather than dominates their personal lives.
