Our 25+ Year History
About SideStarter
The world is changing. For decades, your career was your primary professional asset. Today, the professionals creating the greatest long-term opportunities are also building assets they own—assets that can generate income, expand their influence, create new relationships, and open doors long after a particular job title or employer changes.
We've seen this pattern before. The early days of the internet rewarded those who built websites before everyone else. Social media rewarded those who built audiences before platforms became saturated. We believe we're at a similar moment today. Artificial intelligence, digital distribution, and modern creation tools have made it easier than ever for experienced professionals to package decades of expertise into assets that can compound in value for years to come. Those who start earlier have more time to grow, monetize, refine, and benefit from what they create.
Our team has had the opportunity to work with C-level executives from more than half of the Fortune 500, over 90% of the Am Law 200, thousands of business owners, venture capitalists, entrepreneurs, and other accomplished professionals. Along the way, we've helped professionals publish books, launch webinars, build thought leadership platforms, join advisory boards, grow businesses, and create opportunities far beyond their day jobs.
Throughout that experience, one theme became impossible to ignore: some of the best ideas almost never happen. Busy executives and experienced professionals often have the expertise, vision, and motivation to create something meaningful, but not the time, team, or roadmap to bring it to life—especially in a way that fits alongside demanding careers and family responsibilities.
That's why we created SideStarter.
Inspired by the collaborative spirit of the Italian Renaissance bottega, SideStarter combines experienced strategists, editors, designers, developers, marketers, and operators into one integrated team. Rather than asking professionals to figure everything out themselves, we provide the systems, expertise, and execution needed to transform an idea into a professional asset they own—faster, with less risk, and with significantly greater leverage.
Whether your goal is to write a book, launch a podcast, develop an app, package your expertise into intellectual property, or build a business, our mission is the same: to help exceptional professionals create something that continues working for them for years to come.
SideStarter (formerly Aspatore Ventures) was founded in 1999 by Jonathan Aspatore and is headquartered in Marin County, California, just north of San Francisco, with team members across the United States and an upcoming office opening in Italy in 2027.
Our Manifesto: Every Professional Should Own Something
That model is changing.
Today, the professionals creating the most freedom, influence, and long-term value are doing more than advancing their careers. They're building assets they own.
Some write books that establish their authority. Others launch podcasts that connect them with remarkable people. Some develop software, package their expertise into intellectual property, or build businesses that continue creating value long after the work is done.
These aren't hobbies. They're professional assets.
Unlike a résumé or job title, an asset belongs to you. It can appreciate over time. It can create income, attract opportunities, expand your network, and continue working even while you're focused on your career.
We believe every experienced professional has enough expertise to build one.
The timing matters.
When the internet first emerged, those who built websites early gained an enormous advantage. When social media took off, those who consistently built audiences became the creators, educators, and thought leaders millions follow today. Those opportunities still exist—but the easiest days to start have passed.
We believe we're at another defining moment.
Artificial intelligence, modern software, digital publishing, and global distribution have dramatically lowered the barriers to creating something meaningful. What once required a company, a publisher, or a large team can now often be accomplished with the right strategy, expert guidance, and modern tools.
The professionals who begin building today won't just create another project. They'll create years of additional compounding value.
Every year your asset exists, it can gain more readers, listeners, customers, users, referrals, credibility, relationships, and revenue. The earlier you start, the longer that compounding has to work in your favor.
That's why we believe every accomplished professional should be asking a different question.
Not:
"What's my next job?"
But:
What should I build that I'll own for the rest of my career?
At SideStarter, that's our mission.
To help exceptional professionals transform decades of experience into books, podcasts, apps, intellectual property, and businesses they own—assets that create new opportunities, generate long-term value, and continue opening doors throughout their careers and beyond.
Because your career creates income.
The assets you own create optionality.
Leadership
Jonathan Aspatore
Jonathan is the Founder and CEO of SideStarter, and for the last 25+ years has been a serial entrepreneur who is passionate about starting and scaling new businesses.
Jonathan’s primary role at SideStarter is to conceive new business ideas, work with leaders of our in-house businesses, and collaborate with professionals we help start a business.
Jonathan has been an advisor and board member for numerous businesses, ranging from startups to Fortune 500 companies. He has authored seven books on entrepreneurship, and most recently authored a book on (attempting to achieve) work-life balance as a Dad (The WonderDads Way). He also mentors aspiring entrepreneurs at all levels, from high school students to professional athletes finding their way.
He is an avid tennis player, having played at the University of Pennsylvania and later served as an Assistant Coach for five years at St. Mary’s College in the West Coast Conference.
He is a lover of dogs and all things Italian, and is also an Italian citizen.
Jonathan is based in Marin County California, where he lives with his wife, two sons and two dogs.
Leo Prada
Leo is the Chief Financial Officer for SideStarter and manages financial matters for all our portfolio companies. He is a results-driven finance executive with extensive experience in Strategic Finance, FP&A, M&A, OpEx management, and corporate accounting at companies such as Ask Jeeves, Ask.com, Dictionary.com, and IAC. Leo is a forward-thinking finance executive and entrepreneur who enhances operations through automation, increased workflow efficiencies and ERP & BI implementation. Leo spent most of his youth in South America and is fluent in Spanish. He has his bachelor’s from Sonoma State University.
Keri Ribardiere
Keri Ribardiere has led growth and helped co-found the family companies of SideStarter for the last 10+ years.
Keri has previously worked with numerous business to consumer companies, including The Orange County Register and The Walt Disney Company.
Keri attended Cal State Long Beach and has her Bachelor’s in Business Administration.
Outside of the office she is a lover of dogs and all things Disney.
Danny Schmieding
Danny is the Chief Product Officer for SideStarter and manages the product and user experience for its portfolio companies.
Data-driven and design-inspired, his mix of marketing testing and business sense have given him a unique perspective into how to grow from idea to launch to operations quickly, confidently, and efficiently.
Previous roles at various small businesses, including his own in the health & fitness industry over the decades, have helped hone his ability to work with and motivate executives and entrepreneurs.
Danny studied digital design at the Academy of Art University in San Francisco, as well as Historiography at Sonoma State University.
He is currently based in central Texas with his wife, two sons, and giant dog that could pass for a small cow.
Sara Pickett
Diane Robertson
Our Principles
Case Studies
ASPATORE BOOKS
Aspatore Books began when Jonathan Aspatore got his first book deal from McGraw Hill as a 21-year-old.
In order to convince them he was capable of writing such a book, he received letters of recommendation from business leaders he reached out to that agreed to be interviewed for the book. After publishing this book and 5 others with McGraw-Hill and Houghton Mifflin in a 2-year period, he took the concept and founded his own publishing house, Aspatore Books.
Aspatore Books turned interviews with top business executives, lawyers and entrepreneurs into chapters in thousands of books it published over it’s 10-year history. At it’s height, Aspatore Books was publishing over 500 books and 5,000 professionals a year, making it one of the five largest business book publishing houses by number of annual titles. Thomson Reuters eventually acquired Aspatore Books as the team was already in the process of starting several new companies.
Jonathan recognized the interest in business professionals and lawyers wanting to get published, but not sure how to approach the process. This theme has continued to play out over the last 20 years in our professional businesses we’ve started, helping them utilize new digital media (webinars, and now A.I.), get on advisory boards, and start a side business.
EXECSENSE
ExecSense was built to solve a simple but growing problem: senior leaders needed practical, real-world insight—not theory—from people who had already been there. From its earliest days, ExecSense focused on delivering on-demand executive intelligence created by experienced business, legal, and financial professionals for peers facing real decisions.
Over time, ExecSense developed one of the largest professional learning libraries serving senior executives and corporate professionals, offering content designed to fit into the realities of busy leadership roles.
Key highlights included:
- Thousands of expert-led webinars featuring executives, attorneys, consultants, and industry specialists
- A substantial library of eBooks, reports, and executive briefings
- Podcasts and digital content focused on timely business, legal, and leadership issues
- A practical, experience-driven approach to executive education and professional development
This positioning allowed ExecSense to become a trusted resource for professionals looking to stay informed in a rapidly changing business environment.
ExecSense was acquired by the Financial Times, then part of Pearson plc, marking a significant milestone in the company’s history. The acquisition reflected the value of ExecSense’s deep content library, executive audience, and practitioner-driven approach to professional learning.
Under the Financial Times umbrella, ExecSense aligned with a global brand known for high-quality business journalism, analysis, and executive insight, further validating its role in the executive education and information ecosystem.
ExecSense’s legacy is rooted in its commitment to real expertise, real experience, and real value for leaders. It demonstrated that executive learning is most powerful when it comes directly from those who have navigated the challenges themselves—and when it respects the time, intelligence, and responsibility of its audience.