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Founder’s Friday featuring Brett Siegal @ Ruuster

Brett Siegal

Please provide a brief description about your company.
Ruuster is the first “homebuying management platform” empowering thoughtful and ambitious homebuyers throughout their whole homebuying journey with the tools, resources, and people they need to accomplish their dreams confidently. Our resources and tools are free for consumers and we monetize by connecting homebuyers to vetted industry partners in a first-of-its-kind centralized marketplace of agents, lenders, insurance companies, etc.

What are your top tips for balancing work and life?
Don’t sacrifice things that matter for things that don’t. Relationships matter, family matters, health matters, being involved in communities matters. If you’re not broadly fulfilled, no amount of money or professional success will bring happiness. And the inverse is also true, broad fulfillment, even if that means working fewer hours, will lead to more productive hours worked. This is admittedly hard to achieve and a perfect balance isn’t practically achievable most of the time(especially in the early stages of a startup!), but having this as your north star will give you a fighting chance to enjoy any success you’re fortunate to have down the line.

What is something new that you learned about running a business this year?
Raising capital isn’t just something you do at the right phase of the development of your business. If you are going to need to raise capital to exist, you need to execute your business early on in a way that makes it investable at the time you are going to need to raise capital. Despite the hype, your job isn’t actually to hit “product/market fit” at the earliest stage, it’s to exist and thrive in 12 or 24 months, and so, instead, you really need to hit “company/investor” fit at the time you need capital. Getting capital when you need it may or may not require product/market fit or revenue or certain conversion or traffic or usership – it all depends on your business model and your team and how investors would underwrite you and your type of business – and that should dramatically impact how you allocate precious resources at the beginning of your lifecycle as a business. So you need to talk to investors at the stage ahead of where you are before you start executing on that stage of the business. At the idea stage talk to angel investors, at the angel stage talk to seed investors, etc. Plus fostering long-term relationships with investors (especially when you don’t immediately need capital) is a great idea anyway!

What is a legal mistake you wish someone warned you about?
You get what you pay for in legal advice! Cheap legal advice is very expensive. Make sure you go the best (like Meyer Law!) and get specialty help where needed.

When running your business, what do you struggle with most?
There’s so many things you can do, but limited resources to do it. Culling your great ideas in favor of the greatest ideas is important but always feels like you’re giving up a part of yourself while you’re doing it.

What advice would you give to yourself at 25 years old?
Invest time in building a personal network and personal brand that is independent of the company you are working for. It’s hard to prioritize allocating time to non-work work – you’re tired at the end of the day and want to have fun, but having relationships and having credibility outside of your day job is a huge personal asset you’ll benefit from as you move through your career.

Tricia Meyer 301

Tricia Meyer is Founder + Managing Attorney of Meyer Law, one of the fastest growing law firms in the United States. Meyer helps entrepreneurs and technology companies from startups to large corporations with day-to-day matters and notable clients include companies that have appeared on Shark Tank to companies gracing the Inc. 500 to some of the largest companies in the world.

Tricia has been named on the Forbes Next 1000 list, is one of the Most Influential Female Lawyers in Chicago according to Crain’s Chicago Business and been recognized as a top 10 technology lawyer.

As an entrepreneur and a lawyer, Meyer has a unique perspective and has mentored thousands of startups and scaling companies at tech incubators and accelerators across the United States such as 1871, WeWork Labs and Techstars. Tricia has been featured in Inc., Crain’s, Chicago Tribune, NBC Chicago, American Express OPEN Forum, and more. Learn more at and follow Meyer Law’s story on Instagram @loveyourlawyer.