@Scott Graham Thanks, I have been very fortunate. I borrowed money from my Dad first to do my first flip. He is pretty care free with his money and it was not doing anything for him (he literally had it in cash, wow) so there was not much hesitation there. After that I borrowed money from my brother, @Adam Detigfor material purchase on the same flip. At that point I had turned him onto real estate so he was up to his ears in research and learning using bigger pockets so he was super excited to get involved.
Later I borrowed money from my mom to buy a 'buy and hold' property. I was able to return her money quickly after I refinanced the property into my LLC. She was also not too hesitant to loan the money. I verbally talked through my out options with the property and made sure she understood what I was doing and what options I had if something went wrong.
Because I was able to repay her quickly with more than expected interest (I threw in an extra $500 when I repaid her) she was more than willing to send me a check to purchase the flip house I am closing on tomorrow.
While an over the phone discussion worked for Mom, Dad, and Brother, I took a much different approach when asking to borrow money from my grandparents. They had loaned me school money in the past which I had faithfully repaid over the last 5 years so there was some history established. When approaching them I wrote a very long email giving them the who, what, when, where, why and how answers. I broke down the cash flow and even double or tripled my expenses in the analysis to show them that even being super conservative it is still a good deal. Thankfully I was lucky enough to get a 85K property that grosses 2250 a month in contract so I had plenty extra to inflate the expenses and still show a good positive cash flow. After the email was sent we talked via facetime 2 or 3 days later and they said they were willing to loan me the money but 5% (which is what I purposed) was not going to work. They would not take over 2.5% interest.
So far this process as been extremely smooth with no issues, which I am very thankful for. My first flip goes on the market tomorrow. I am a little anxious to repay the loans as this is my first flip I know it is not truly successful until the check is in hand. After that closes and I can repay some of these loans I am sure the confidence with my family will increase which will hopefully lead to future borrowing opportunities.