Top Illinois Software Angel Investors

Last updated: December 5, 2024
Top Illinois Software Angel Investors

Illinois is known for its booming software sector, boasting exceptional startup growth. The state is home to nearly 10 software unicorns and the sector has generated more than $1B in 2023.

That being said, there are hundreds of angels who are ready to invest in software startups and boost their growth.

But!

How do you determine which investor is the most active one and matches your mindset?

Well, that is what the following list of top 8 angel investors in Illinois is meant for.


Find out The List of The Top 8 Angel Investors in Illinois Who Fund Software Startups

Investor NameFocused SectorsFunding StagesNotable InvestmentsInvestment Range
Charles BossartConsulting, Financial Services, IT, Advertising, Software, InsuranceEarlyNomios, Commodity Blenders, TLC CompaniesUp to $1M
Tim HogaboomSoftware, AI, Big Data, Biotechnology, Health Care, TherapeuticsEarlyNuo Therapeutics, X4 Pharmaceuticals, Aileron TherapeuticsUp to $200K
Christopher GraberMedical Devices, Financial Services, SaaS, Clinical Trials, BiotechEarlyEastern Dental, Anovia Payments, Jazz Pharmaceuticals$50K - $500K
Ben ConradHealthcare, Veterinary, IT, Software, EducationEarlyQualDerm Partners, Verisys Corporation, HHA eXchange$50K - $500K
Andrew RocheE-Commerce, Retail, Child Care, Health Care, IT, PersonalizatioEarlyXixi Maternal and Baby Care, It's U, Beilai YoupinUp to $250K
Jeff VranekElectronics, Real Estate, E-Commerce, Healthcare, Market ResearchEarlySurvey Sampling Intl, Riverchase Dermatology$50K - $500K
Richard McClainConsulting, Financial Services, IT, Transportation, InsuranceEarlyCommodity Blenders, TLC Companies, Claims Recovery Financial Services$25K - $300K
Ryan MilliganIT, Software, Legal Tech, Big Data, IT ManagementEarlyCommodity Blenders, TLC Companies, Claims Recovery Financial ServicesUp to $200K

Before moving on to the list of the top-ranked investors in Illinois, it is recommended to do in-depth research and understand the:

  • Investment Interests
  • Investment Range
  • Funding Preferences
  • Required ROI
  • Portfolio Deal Closings  

Enough talk, let’s get started!

Charles Bossart

  • Reach Out:Charles Bossart | LinkedIn
  • Focused Sectors: Consulting, Financial Services, Information Technology, Insurance, Transportation, Advertising, Mobile Apps, Software, Technical Support
  • Present In: Illinois
  • Notable Investments: Nomios, Commodity Blenders, TLC Companies, SourceGate Systems

Known as the senior investor at High Street Capital, Charles Bossart is also a famous individual angel investor. He has been making personal investments for more than a decade and usually invests at the early stage.

With a strong focus on lower-middle market investments, Charles Bossart looks for startups that are expected to have high growth and don't have a lot of competitors. As an investor, he invests in seed-stage businesses and has more than 13 years of experience in buy-side investment management across multiple asset classes, including structured fixed-income, publicly traded equities, and private equity.

The investment range of Charles Bossart can range up to $1M, depending upon the startup's sector and estimated ROI.

Tim Hogaboom

  • Reach Out:Timothy Hogaboom | LinkedIn
  • Focused Sectors: Software, AI, Big Data, Biotechnology, Clinical Trials, Health Care, Pharmaceutical, Therapeutics, Biopharma,
  • Present In: Illinois
  • Notable Investments:  Nuo Therapeutics, X4 Pharmaceuticals, Ocata Therapeutics, Lightwave Logic, Aileron Therapeutics

Tim Hogaboom is an angel investor with a strong focus on biotech and software startups. He has been actively investing in startups since joining Lincoln Park Capital in 2017 and prefers to invest in early-stage companies, particularly those that are women-founded or Hispanic/Latinx-founded.

When investing in businesses, Tim Hogaboom prefers to fund startups that are fostering innovation and can easily generate 2-5x ROI, within 24 months of investment. The average check size of Tim Hogaboom can range up to $200,000.

Christopher Graber

  • Reach Out:Christopher Graber | LinkedIn
  • Focused Sectors: Medical Devices, E-Commerce, Financial Services, Computer Vision, Software, Clinical Trials, Dental, Computer, SaaS, Human Resources, Recruiting, Biotechnology, Pharmaceutical
  • Present In: Illinois
  • Notable Investments: Eastern Dental, Anovia Payments, Jazz Pharmaceuticals

Funding startups for around 5 years, Christopher Graber is an active angel investor who usually makes private and venture investments along with Waud Capital Partners.

Graber's interest in the healthcare sector isn't a coincidence. He has a great educational background in the medical industry.  Before joining Waud Capital, he worked in investment banking at Robert W. Baird & Co. and has also worked with other investment networks.

The average check size from Christopher Garber can range up to $1M, depending upon the estimated ROI and target market.

Ben Conrad

  • Focused Sectors: Health Care, Software, Veterinary, Information Technology, Medical, Management Information Systems, Medical Devices, Education, Women-Led,
  • Present In:  Illinois
  • Notable Investments: QualDerm Partners, Verisys Corporation, HHA eXchange, Unitek Learning, People, Pets & Vets

Known as one of the most active investors in Chicago, Ben Conrad usually has a strong interest in funding early-stage companies that are women-led or have innovative solutions in their respective fields.

He has a strong finance-related background and has extensive experience in private equity and venture capital firms. When investing in businesses, Ben Conrad focuses on startups that are solving modern software problems in the fields of health, finance, telecommunications or graphics. He invests in startups by participating in fundraisers or other startup programs.

The investment range of Ben Conrad lies between $50,000 to $500,000.

Andrew Roche

  • Focused Sectors: E-Commerce, Electronics, Retail, Baby, Children, Service Industry, Art, Education, Media and Entertainment, Fruit, Child Care, Health Care, Personalization, Information Technology, Software, E-Learning, Quality Assurance, Training
  • Present In: Illinois
  • Notable Investments: Xixi Maternal and Baby Care, It's U, 51Testing, Yaspeed, ACG, Lianguo Wang, Beilai Youpin

Andrew Roche is a principal at CIVC Partners, where he focuses on investments in the information technology sector. He has been actively funding startups since joining CVC in 2016.

Similarly, Andrew prefers to invest in early-stage companies, particularly those that offer innovative solutions in IT consulting and outsourcing. He invests in startups that have a unique idea with minimal market competition and can provide huge returns.

The investment range of Andrew Roche can range up to $250,000.

Jeff Vranek

  • Focused Sectors: Electronics, Real Estate, Real Estate Investment, E-Commerce, Retail Technology, Software, Transportation, Health Care, Health Diagnostics, Medical, Business Development, Market Research
  • Present In: US
  • Notable Investments: Survey Sampling International, Riverchase Dermatology and Cosmetic Surgery, Tee International, Move This World, DRB Systems

Jeff Vranek is a notable angel investor with a strong interest in early-stage startups. He has been actively funding startups since 2018 and is known for his hands-on approach, often participating in screening contests and pitching events to find promising ventures.

When investing in businesses, Jeff prefers startups that demonstrate innovative solutions and have a clear path to scalability.

He invests in startups that can at least generate 3x ROI within the first 2 years of the funding and has an investment range of $50,000 to $500,000.

Richard McClain

  • Focused Sectors: Consulting, Financial Services, Information Technology, Insurance, Transportation, Advertising, Mobile Apps, Software, Technical Support
  • Present In:  
  • Notable Investments: Commodity Blenders, TLC Companies, SourceGate Systems, Claims Recovery Financial Services, LLC

Richard McClain is an angel investor with a strong focus on technology and consumer goods startups. He has been actively funding startups since 2015 and prefers to invest in early-stage companies, particularly those that demonstrate innovative solutions and have a clear path to scalability.

As for his background, Richard studied at Harvard Business School and has worked in various roles in investment banking and private equity, where he developed a keen eye for identifying high-potential startups.

The investment range of Richard McClain lies between $25,000 to $300,000.

Ryan Milligan

  • Reach Out:Ryan Milligan | LinkedIn
  • Focused Sectors: Information Technology, Software, Legal Tech, Big Data, IT Management, Computer
  • Present In:  Chicago
  • Notable Investments:  Profisee, ATP, SurePoint Technologies

Ryan Milligan is a partner at ParkerGale Capital and an active investor in the software sector. Funding startups since 2014, Ryan Milligan has invested in many startups and often prefers early-stage businesses with a high ROI.

Like most other investors, Ryan Milligan usually makes his personal investments through extra startup events or growth programs. He also participates in fundraisers and has a strong preference for investing in businesses that are offering scalable solutions.

The investment range of Ryan Milligan can range up to $200,000.

Wrap-Up:

Ending the list on a shorter note, remember that not all angel investors have a similar mindset and at some point, you will need to face rejections.

The most important part of submitting your pitch deck is to be confident and to be able to bear with the results. Two general tips that can help you secure funding from angel investors include:

  1. Study the mindset of your targeted investor.
  2. Always include the “profitability factor” in your pitch deck and add solid reasons why the investors should fund your startup.
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