Tope Awotona built Calendly from a $200,000 personal investment into a $3 billion company—one of the rare immigrant founders to achieve billionaire status while maintaining majority ownership. His journey from Lagos, Nigeria to Georgia at age 15, through American higher education and corporate roles, to founding one of tech's most successful bootstrapped companies represents both the promise and complexity of the U.S. immigration system for high-skilled professionals and entrepreneurs.
The trauma of losing his father created the catalyst for immigration, but also instilled a resilience that would define Awotona's entrepreneurial journey. Arriving in Georgia as a teenager meant navigating American high school, cultural adjustment, and the complexities of maintaining legal immigration status—challenges familiar to many international students and recent graduates.
After completing his undergraduate education, Awotona spent years in corporate sales and business development roles at major technology companies including EMC Corporation and IBM. This period—spanning roughly a decade—built the business acumen, industry knowledge, and capital reserves that would later fuel Calendly's creation.
In 2013, Awotona founded Calendly with approximately $200,000 of his own savings, bootstrapping the automated scheduling platform for its first eight years. The company addressed a universal pain point—the back-and-forth email chains required to schedule meetings—with elegant simplicity that scaled globally.
By early 2021, Calendly had some 10 million monthly users and more than 50,000 company customers, including 116 of the Fortune 500. The company's Series B funding round that year, led by OpenView Venture Partners and Iconiq Capital, valued Calendly at $3 billion. Awotona retained a majority stake—extraordinarily rare for venture-backed companies—making him one of the few Black tech founders to achieve billionaire status.
While Awotona has not publicly disclosed his specific immigration pathway, his timeline and circumstances reveal common routes followed by thousands of high-skilled immigrants building careers in the United States.
Most immigrant founders who arrive as teenagers or attend U.S. universities begin on F-1 student visas. After completing their degrees, they typically transition to Optional Practical Training (OPT)—a period of work authorization directly related to their field of study. For STEM graduates like Awotona, extended OPT can provide up to three years of work authorization.
Working at established companies like EMC and IBM likely provided Awotona access to employer-sponsored visa pathways. Large technology companies routinely sponsor H-1B visas for foreign national employees, followed by employment-based green card petitions for valued talent they want to retain long-term.
The employment-based immigration system issues approximately 140,000 green cards annually across five preference categories, with most high-skilled professionals qualifying for EB-2 or EB-3 categories. Processing times typically span 2-5 years from initial filing to green card approval, though this varies by category and country of origin.
For entrepreneurs, this timeline creates complexity—starting a business while on employer-sponsored status requires careful legal planning to avoid jeopardizing immigration status.
Immigrant entrepreneurs face a unique set of constraints that native-born founders never encounter, shaping business decisions and growth trajectories in fundamental ways.
H-1B visas tie employees to sponsoring employers, creating significant barriers for entrepreneurship. Starting a company while maintaining H-1B status requires either:
These constraints often force immigrant founders to delay launches, bootstrap longer than ideal, or turn down opportunities that would require leaving stable employment and visa sponsorship.
Venture capital firms sometimes hesitate to invest in immigrant founders without permanent residency, concerned about potential immigration complications affecting business continuity. While visa status does not prevent equity ownership, founders must have proper work authorization to perform services for their company. This nuance can contribute to investor concerns.
The data reveals stark disparities: Black-founded startups received less than 0.5% of U.S. venture funding in 2023. Awotona's decision to bootstrap Calendly for eight years may reflect both strategic choice and the challenges of accessing institutional capital as both an immigrant and Black founder.
For founders navigating these complexities, Alma's startup immigration services provide specialized support for 1-25 foreign nationals with transparent pricing and fast turnaround times that match the pace of startup growth.
Several visa categories offer pathways for immigrant entrepreneurs, each with distinct requirements and strategic considerations.
The O-1 visa for extraordinary ability provides one of the most flexible options for immigrant founders. Unlike H-1B visas tied to specific employers, O-1 status allows work for multiple entities—including your own startup—as long as you have a qualified sponsor.
For successful professionals with strong track records, the O-1 offers entrepreneur-friendly flexibility. Alma's O-1 New services start at $8,000 for new petitions with a guaranteed two-week document processing turnaround.
The EB-2 National Interest Waiver allows qualified individuals to self-petition for a green card without employer sponsorship—ideal for entrepreneurs. NIW applicants must demonstrate their work benefits U.S. national interests and that waiving the standard labor certification requirement serves America's interests.
Successful NIW petitions typically show:
The EB-2 NIW pathway has become increasingly popular among STEM professionals and entrepreneurs seeking permanent residency independence from employer sponsorship.
Awotona's success exemplifies documented patterns in immigrant entrepreneurship that drive American innovation and economic growth.
The numbers reveal immigrants' outsized entrepreneurial contributions:
These statistics demonstrate that immigrant entrepreneurship isn't an outlier—it's central to American business formation and economic dynamism.
Research shows immigrants are significantly more likely than native-born Americans to become new entrepreneurs. Several factors explain this pattern:
Nigerian immigrants specifically demonstrate the highest education levels of any immigrant group, with about 67% holding bachelor's degrees or higher—nearly double the national average. This educational foundation creates fertile ground for entrepreneurial success.
Awotona's path from teenage immigrant to billionaire founder offers actionable insights for those navigating similar journeys.
The median time from entering the U.S. to starting a business for immigrant entrepreneurs is about 13 years. This timeline reflects the reality that most founders need to establish stable immigration status before launching companies.
Early consultation with immigration attorneys prevents costly mistakes and identifies optimal pathways. Alma offers free consultations to explore visa options and receive personalized guidance.
Whether pursuing O-1 or EB-1 petitions, documentation proves essential. Start building evidence early:
This portfolio becomes invaluable when petitioning for entrepreneur-friendly visa categories.
The immigration legal process involves complex regulations, frequent policy changes, and high stakes. Consult an attorney when:
Professional guidance prevents errors that can delay cases by months or years. Alma's platform combines expert attorneys with technology for fast turnarounds—guaranteed two-week document processing—and 99%+ approval rates.
Quality legal representation dramatically affects immigration outcomes, processing times, and entrepreneurial flexibility.
Not all immigration attorneys understand entrepreneurial needs. Essential qualities include:
Traditional law firms often lack the speed and transparency startups require, with opaque billing and slow communication creating unnecessary stress.
Modern immigration platforms combine legal expertise with technology to deliver superior experiences:
Alma's business immigration platform provides these capabilities for founders scaling from solo entrepreneurs to companies managing dozens or hundreds of foreign nationals, with transparent per-case pricing and integration with HRIS systems.
The journey from temporary visa status to U.S. citizenship typically spans a decade or more, involving multiple stages with distinct requirements.
Employment-based green card processing involves several steps:
Country-specific quotas create significant disparities, with nationals from India and China facing backlogs exceeding 10 years in some categories, while others process relatively quickly.
The U.S. issues approximately 140,000 employment-based immigrant visas annually across five preference categories. Family-sponsored immigration accounts for about 64.6% of all legal permanent resident admissions, though employment-based categories remain critical for high-skilled professionals.
After obtaining permanent residency, the path to citizenship requires:
Citizenship provides absolute security—no visa renewals, no risk of status loss, and the right to vote and sponsor family members for immigration. For entrepreneurs, it eliminates any remaining immigration-related business constraints.
As Calendly scaled from Awotona's solo project to a company serving millions of users, his immigration story evolved from individual visa holder to corporate immigration sponsor.
Building a team often means hiring foreign national talent, transforming founders into petitioners who navigate corporate immigration obligations:
Startups managing 26-250 foreign nationals need structured immigration operations. Alma's Growth Plan provides:
This infrastructure prevents the chaos that often accompanies rapid hiring growth, ensuring compliance while minimizing administrative burden.
Ready to begin your own immigration journey toward entrepreneurial success? Follow these concrete steps.
Schedule a free consultation with an immigration attorney to:
Alma's immigration experts provide personalized assessments that account for your specific circumstances, career trajectory, and entrepreneurial ambitions.
Start building your extraordinary ability portfolio now:
These materials become essential for O-1, EB-1, or EB-2 NIW petitions.
Immigration represents a significant investment in your future. Typical costs include:
Alma provides transparent pricing with no hidden fees. All administrative charges, platform access, and up to three attorney consultations included in quoted fees. Payment plans available for business clients.
The investment in proper legal support prevents costly mistakes and denials that can derail careers and business plans. With Alma's 99%+ approval rate and two-week document processing guarantee, you get speed, excellence, and care—the foundation for immigrant entrepreneurial success.
Awotona has not publicly disclosed his specific immigration pathway. His arrival at age 15 with family following his father's death could align with several visa categories, including family-based immigration. After establishing legal status, he would have navigated the transition to work authorization and eventually permanent residency, though the exact timeline and visa types he used remain private.
Founders on H-1B or other employer-sponsored visas face constraints when starting businesses. Common strategies include maintaining full-time employment with the sponsoring employer while building the business part-time, having the new company become the H-1B sponsor, or waiting until obtaining permanent residency before launching full-time. Awotona's decade of corporate experience before founding Calendly in 2013 suggests he may have secured permanent residency during his time at EMC or IBM, though he has not confirmed this publicly.
Yes, visa status does not legally prevent foreign nationals from raising venture capital, owning equity, or operating businesses in the United States, though founders must have proper work authorization to perform services for their company. However, some investors express concern about immigration uncertainty affecting business continuity, which can create additional friction in fundraising. Obtaining permanent residency removes any investor concerns about immigration status and provides greater operational flexibility.
Nigerian immigrants demonstrate the highest educational attainment of any immigrant group in the United States, with about 67% holding bachelor's degrees or higher—nearly double the national average. This strong educational foundation, combined with English language proficiency (Nigeria's official language) and cultural factors that emphasize professional achievement, creates favorable conditions for entrepreneurial success. However, Nigerian founders still face systemic barriers including limited venture capital access, with Black-founded startups receiving less than 0.5% of U.S. venture funding in 2023.
For high-skilled immigrants following the most common pathway, the timeline typically spans 12-20 years: F-1 student visa (4 years undergraduate), OPT work authorization (1-3 years), H-1B status (3-6 years while green card processes), employment-based green card processing (2-5 years), permanent residency (5 years before naturalization eligibility), and naturalization (6-12 months processing). Country-specific quotas dramatically affect timelines, with nationals from India and China facing significantly longer backlogs in some employment-based categories.
Yes, Alma offers a dedicated startup immigration plan for companies with 1-25 foreign nationals, providing streamlined legal support with flat-rate per-visa pricing, two-week document preparation turnaround, and transparent costs. The platform includes guided workflows, compliance tracking, and case management designed for fast-moving startups. For scaling companies managing 26-250 foreign nationals, the Growth Plan offers custom pricing with structured workflows, automated compliance alerts, and dedicated attorney support.
