Joe DiPasquale is the founder and CEO of, the premiere social media platform for
schools, companies, and organizations that empowers them to support and manage their constituents’ communication. Regroup, which secured a round of venture funding from HighBAR Ventures last year, provides an group communications platform for organizations that integrates with Facebook, SMS messages, email, and more. He is also one of the a co-founders of StartOut, an organization dedicated to fostering and developing entrepreneurship within the LGBT community. He is a member of the New York Tech Meetup Community Committee.

1. You worked in both banking, consulting, and media for big companies. Is it sweet to be your own boss? How did you start Regroup?
I’ve been fortunate to have bosses in the past who let me effectively be my own boss (with clear goals), which I think is always a great way to manage. I started Regroup out of a need I found when in business school at Stanford – I saw all the students going outside of the school to communicate, and Stanford didn’t adequately support our needs to communicate. So I linked up with some others and we started a site that could be used by students at a school (and eventually by the schools themselves to support their students), providing a more robust feature set for group communication while integrating with the other platforms students are using (SMS, facebook, email, etc).

2. What inspired you and your co- founders to start Startout?
We all wanted a way to learn from other LGBT entrepreneurs, while developing LGBT entrepreneurship and helping others. We’re starting a lot of awesome programs such as a mentorship program, capital connections, monthly events (in NY and SF to start), and more. I’m very excited about it.

3. How are you planning to reach out to the gay community to find other potential entrepreneurs?
We’ve all relied on each other to help spread the word. We’re hoping it will grow over time and as we build a core group of good people, things will build. We had over 150 people at our first meeting in NY, so things are off to a good start.

4. Startups are notorious for being able to get a lot done for little or no money. What are some money saving tips could you pass on budding entrepreneurs?
This is a hard question, because hindsight is 20/20. Meaning: there are always ways you can save money, but it’s rare that you know them ahead of time. If you try to build a profitable company from the beginning, I think you’ll always be very conscious of your burn. Probably the best way to save money is to review monthly your burn and balance it with the revenue you’re earning.

5.  So I hear you spent some of your childhood in Alabama (as did I). How has living in a big city changed what how you spend money?
Obviously some things are more expensive, like your apartment, movies or food. And then also patterns change: in NYC it’s so easy to grab food on the way home that I find myself making food less. I think the base cost is just higher. But the things I tend to buy haven’t changed much.

6. What personal finance applications do you use or money-oriented websites do you read?
I DVR Suze Orman; she’s great because she makes it fun to think about your finances. I recently read Andy Tobias’ “My Vast Fortune” and loved the memoir-style advice on going through life and his lessons-learned about how he navigated the financial waters. One of the best resources, I think, is always just listening to what people who’s been there/done that have to say. Running a business has also made me more diligent personally – when you put a lot of energy into organizing a business’ finances, it’s easier to take small steps to start organizing your own finances.

7. When you were a kid, did you get an allowance?  What would you buy?
I did; it was $5 a week but it wasn’t consistent. (Unless I was building towards something in which case I would nag my parents). I remember when Crazy Eddie was going out of business and getting really excited b/c Nintendo games that could be $40-$50 were $20. I made my parents buy me a ton of games.

8. What is the one personal item that you always splurge on?
Food, but not “good” food, just a lot of food.

9. What is the one thing that you feel is always overpriced?
I think everything is overpriced. But I think paying $10 for internet at airports/hotels is ridiculous.

10. If money can’t buy happiness, what can it buy?
I think money can do a lot, e.g. the Gates Foundation. Money can save lives.

Read other Queercents interviews in the Ten Money Questions archive.